How to Plan an Incredible 3 Day Portland Itinerary

We love Portland for many reasons. The innovation in the food and drink scene is almost unrivaled (we’ll get into why we think that is below). Within 90 minutes, you can be either on the Pacific Ocean or in the mountains (we’re mountain people, but we do love the Oregon Coast). The city is compact and easy to get around.

If you’re visiting Portland and looking for a guide to help you figure out the best way to spend your time to experience the best of the city, you’re in the right place. 

We’re Matt and Alysha, and we live in Portland and are here to help you figure out what to do and see, and, most importantly, what to eat and drink on your trip. We’ll use our experiences exploring the city to help you plan an incredible three day foray into what makes Portland special. 

Is it a perfect utopia? No, of course not. Every city has its flaws, and Portland is no different (though the reports you’ve seen on the news are likely a gross exaggeration). 

Is it a great place to spend three days eating, drinking, and exploring? Absolutely 100% yes. 

In this guide, we’re going to cover everything you need to know to spend 3 days in Portland (at least everything we think you need to know). 

We’ll start with the logistics – the best time to visit, where to stay, and other things you need to know for a smooth trip – and then go into a complete 3 day Portland itinerary that you could copy and paste for your own trip, if you wanted (we support plagiarism in this very narrow context). 

Sound good to you? Let’s get into it. 

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

What Can You See With 3 Days?

At a high level, we think three days is a good amount of time to spend in Portland, which is a relatively compact city compared to other major west coast cities. 

Three days gives you enough time to see the highlights, eat and drink your way through one of the best food cities in the country, AND get out of the city for a half day or so to experience one of Portland’s best day trips (which we would say is one of the highlights). 

At a high level, Portland is split into two halves by the Willamette River, and each half of the city has a distinct vibe that we think is worth experiencing (we get frustrated when people spend their entire trip in downtown Portland, which is fine, but not where we think Portland shines). 

We generally recommend spending a day on each side of the river, and having three days gives you the time to do that. 

Over the course of those three days, you’ll get a taste for what made us fall in love with Portland and choose it as our forever home after spending a few years on the road full time: the green spaces within the city limits, easy access to world-class wilderness within 90 minutes, and, of course, the food and drink culture that is chock full of innovation and alluring options. 

By the end of your trip, we hope you fall head-over-heels in love with Portland like we have. 

Where to Stay

Portland is a fairly compact city, but there is a definite vibe shift when you cross the Willamette River, which splits the city in two, in either direction. 

The west side is more urban and walkable, while the east side is almost a series of suburbs, with some great stretches of commerce where you’ll find many of Portland’s best places to eat, drink, and shop. 

The first thing that we’d say about choosing a place to stay is that the rumors of downtown Portland’s demise are largely overblown. No, there are no protests and riots burning down the city, despite what your uncle might have told you. 

However, that’s certainly not to say that Portland isn’t facing some major issues, particularly around the explosion of the unhoused population over the past few years. 

We’d avoid staying near Chinatown / Old Town on the north end of downtown, where the issue is most visible and prevalent. 

If you want to stay downtown and be able to walk to just about everything, the southern side of downtown Portland near Portland State University, or the Northwest District (we just call it “Northwest”) near NW 23rd Ave are great home bases (our specific recommendations below will reflect this). 

We have an entire guide dedicated to choosing a place to stay in Portland, which you should read for far more detail than we have in this summary. 

There are four areas we recommend, and it depends on what you’re looking for. 

  • Our overall recommendation is to find a hotel on the Central Eastside, which is probably our favorite part of Portland. It’s close to the river, which means you can walk to downtown Portland and all the sights there (don’t miss Powell’s Books!) but it’s a little more residential and, as a result, quieter. We have personally stayed at the Jupiter NEXT Hotel, a beautiful boutique hotel, but we also like some of the more affordable options in the area like the Kex. If you’re looking for a unique stay, look at the tiny homes at Tiny Digs (which is near one of our favorite food/drink stretches in the city on 28th).

  • If it’s your first time in Portland, you can’t go wrong with downtown Portland. Downtown Portland is about as central as it gets, walking distance to…pretty much everything. We’d recommend staying in the southern half of the neighborhood near Pioneer Courthouse Square (check out the budget-friendly Hyatt Centric, the stylish Dossier, or the hip Hotel Zags).

  • For a balance between the location of downtown and the vibes on the Eastside, stay in the Northwest District. You’ll be walkable to downtown and Washington Park (home of the International Rose Test Garden), and right in the middle of some of the best food in the city. Stay at the Inn at Northrup Station, which is a little odd, but is the best hotel in this neck of the woods.

  • If you want a more residential neighborhood full of great places to eat and drink, look at Southeast Portland. It’s our favorite part of Portland (we live in the area!) and the stretches of Division and Hawthorne are two of the best places to wander in the city. The downside is that there are very few places to stay. There are two guesthouses in great locations – Bluebird and Evermore – and a handful of nice vacation rentals (like this studio above the garage and this basement level guest suite). 

Do You Need to Rent a Car in Portland?

The short answer is no, for a three day trip we probably wouldn’t rent a car. 

Most of the time, it’ll be more of a nuisance than anything else, and you’ll be paying a pretty penny to leave it parked in a garage for the majority of the time. 

However, it might be useful to have a car for longer trips (4+ days) where you wanted to do multiple day trips. There are a lot of cool places to visit within 60-90 minutes of the city, and a car certainly makes it easier to get to places like the coast and the Willamette Valley.  

If you only have three days, the day trip we’d strongly recommend is the Columbia River Gorge, land of the waterfalls, and that happens to be relatively easy to access from downtown Portland either by public transit or guided tours (more on that in the actual itinerary below). 

Getting around Portland

One of the reasons we like Portland is the fact that it’s a relatively compact city. Even with traffic (which is getting worse, which seems to be the story of every city in the country) it only takes about 20 minutes to get clear across the city. 

When you zoom in on the areas of the city that most tourists are going to be focused on, it gets even more compact and easy to get around.

For the most part, we’d strongly recommend using a combination of walking, public transit, and ride share apps like Lyft to get around.

Given rental car prices over the past several years, we’d be willing to bet that it actually works out to be cheaper than renting a car anyway. 

Things to Know Before You Visit Portland

Here are a few other odds and ends to keep in mind as you’re planning your trip to Portland. 

Be prepared for rain outside of summer (which is July – September). Pack a raincoat (or an umbrella, but Pacific Northwest locals don’t really use umbrellas like east coasters do).

Restaurants and bars are often closed Monday and/or Tuesday. A lot of our friends and family have come to visit and we’ve learned that Monday and Tuesday are the days where every restaurant we want to take people to is closed. Just something to be aware of. 

If you’re parking downtown, download the official parking app “Parking Kitty.” Yes, it’s the official app. The reason we’d recommend downloading it rather than paying at the parking machines around town is that you can extend your parking session without having to go back to the car, which we find helpful. 

3 Days in Portland: A Complete 3 Day Portland Itinerary

FINALLY. On to the itinerary itself!

We’re going to give you a day-by-day Portland itinerary that we think captures the best of the city.

Most importantly, it’s essentially the exact itinerary we do with our friends and family who are visiting who have never been to Portland before. 

For each day, we’ll be giving you food and drink recommendations that make sense for that day’s itinerary based on location. We’ll give you breakfast + coffee, lunch, and dinner ideas for each day. 

One very important note at the top: If you are in town on a Saturday, we’d make sure to swap around your days so that Saturday is the day that you do downtown Portland (day 1 of the itinerary below). 

The reason? Two of our favorite things to do in Portland only happen on Saturdays, and you shouldn’t miss them! 

They are the PSU Farmers Market, the best farmers market we’ve ever been to (and we’ve been to A LOT of them), and the Portland Saturday Market, which is more of a crafts/art market (it only happens from spring to fall). 

If you’re in town on Saturday, start your “Downtown” day with coffee, head to the PSU Farmers Market, and then walk to the Saturday Market along the river. Here’s a sample route

A quick note up top: Many of the places to eat below are not necessarily gluten free, because Alysha can eat gluten and loves exploring the gluten-full side of Portland’s food scene. If you need to eat gluten free, you should read our guide to gluten free Portland with our favorite Celiac-safe spots.

Day 1: Downtown Portland, Washington Park, and Northwest 

On your first day in Portland, it makes sense to start with the downtown core, which includes many of the more traditional “tourist” sights in Portland. 

Unlike cities like, say, Seattle, who have the Space Needle, Portland doesn’t have any traditional tourist attractions to speak of, and its biggest draw might actually be an independent bookstore. 

But that certainly doesn’t mean it’s not worth visiting. 

Start with a short exploration of downtown Portland, then move up the hill to Washington Park (and the International Rose Test Garden) before heading to NW 23rd Ave for dinner and drinks. 

REMINDER: If you’re here on a Saturday, make sure to do this day on Saturday and hit the PSU Farmers Market and Portland Saturday Market. To do that, we’d suggest going from coffee/breakfast → PSU Farmers Market / Riverfront / Portland Saturday Market → Powell’s City of Books. 

Coffee and Breakfast

Coffee and the Pacific Northwest; name a more iconic duo.

My hypothesis as to why coffee is so synonymous with the region is that sometimes you need something to get you out of bed when the sun is still down at 9am, and another hit to get you through the drizzly gray winter days. 

Plus, is there a better place to hang out on a cool gray day than inside a cozy coffee shop?

Downtown Portland is littered with great coffee shops, and that’s where we think you should start your day.

  • If you’re looking for our overall favorite spot in downtown Portland, head to Less and More Coffee. They have two locations within a few blocks of Pioneer Courthouse Square – an abandoned bus shelter (better for innovative flavored drinks) and a storefront (better for pure coffee, with pour over options). Whether you’re in the mood for a unique latte or want to try a cup of single origin coffee, Ryan and his team have you covered. 

  • If you’re in the mood for what I can only describe as “craft cocktails, but make it coffee” head to Never Coffee. It’s our favorite place to take people who don’t necessarily like the taste of coffee because the highlight is truly their specialty lattes, which are many steps above your typical vanilla latte. For example, our favorite is the Midnight Oil, which is a combination of fennel and star anise. 

For breakfast around downtown, you have a couple of options. Note that we’re saving Fried Egg I’m in Love and their famous breakfast sandwiches for tomorrow, which is why you won’t find it listed here. 

If you’re craving pastries and you’re up for a bit of a walk, definitely head over to Northwest and go to Ken’s Artisan Bakery. It’s an iconic spot, and despite being sold relatively recently (to the employees), the quality here is still outstanding. Get there early or be prepared to wait in line. 

If you’re in the mood for donuts, allow us to take a second to talk about Portland’s doughnut scene, which has become quite famous over the past decade or so. 

The OG spot that you’ve almost certainly heard of is Voodoo

We recently went to a comedy show where the performer was talking about Voodoo, and he made a good observation about their “stick it to the man!” anti-capitalist vibes. They have a location at Disney World now, so they kind of became the man over time. 

Voodoo is, in our opinion, not really worth going to. There’s always a line, the doughnuts aren’t that great (though they’re cheaper than other options), and the location in Old Town is pretty gnarly in terms of the visibility of the unhoused population nearby. 

It’s true that they have some fun flavors, and that they have that nostalgia factor going on, harkening back to a time when Portland was a little more weird and offbeat. 

If you want to experience that, we’d actually head to their second location across the river (here on Google Maps), which is in a better area. 

Here are a few other doughnut spots downtown that are, in fact, worth your time (at least according to, well, us). 

  • Blue Star Donuts: We were talking with a friend who was visiting recently about what niche Blue Star fills in the Portland doughnut scene, and landed on the fact that their flavors tend to be really fun. Come here for the unique flavors, but be prepared to pay for it. They’re also another Portland donut shop that has expanded to have locations all over the country. 

  • Sesame Donuts: If you’re looking for donuts that aren’t fancy and bring you that nostalgic vibe of biting into the crispy crust of an apple fritter or old fashioned, this is the spot. They’re also cheaper than most of the options on this list, and fit the bill for “good doughnuts you don’t have to pay $5 a pop for.” 

  • Petunia’s: If you’re gluten free, this is the spot. As a Celiac, Matt thinks these are among the best gluten free doughnuts in the world. They’re ACTUALLY FRIED, which is a rarity in the gluten free doughnut world, for some reason. Weekends only. They’re also vegan (as is their entire shop).  
A special doughnut from Blue Star
Gluten free (and vegan) doughnuts from Petunia’s

If you’re really looking for the “best” (which is entirely subjective) doughnuts in Portland, you have to head over the river to some combination of Pip’s (mini doughnuts fried to order), Doe (fun flavors), or Delicious (blend of playing the classics/hits and innovative flavors/textures). 

We’re also suckers for the gluten free + dairy free mochi doughnuts at Mikiko, especially on Saturday mornings when they have a fried chicken sandwich between two of their doughnuts (it’s amazing). 

Powell’s City of Books

Powell’s City of Books is our favorite “tourist attraction” in town, but it’s hard to call it touristy when we go there ourselves. In our experience, it’s the best (and largest) independent bookstore in the world. 

It’s so big and vast in its collection that we often walk in with visiting friends and family and pick a time 30-60 minutes in the future when we’ll reconvene in the lobby, otherwise we’ll be there forever. 

They have an excellent collection of sci-fi / fantasy books, graphic novels, travel books, and cookbooks. It’s also worth checking out their bestsellers and staff picks to discover some new books, a regular occurrence for us. 

Walking the Waterfront

Another thing we like to do, particularly on a nice morning, is walk the waterfront along the Willamette River, which runs right through the middle of the city with numerous bridges of different shapes and styles crossing it.

Aside from roses and hipsters, Portland is also known for its bridges.

From Powell’s, we’d take this route to get down to the waterfront. 

Our favorite stretch of the waterfront is from the Hawthorne Bridge up to the Steel Bridge and back along the other side of the river. Here’s a map (we do this as a bike ride fairly often from our house – evidence below).

It’s a 2.5 mile loop that is mostly flat, and offers great views of Portland’s many bridges and downtown Portland (from the east side of the river). It’s really lovely. 

However far you go, you’ll want to end close to Pioneer Courthouse Square so that you can hop on the MAX to get up to Washington Park, your next stop. 

Exploring Washington Park

Washington Park is not the biggest park in Portland, but it is the most action-packed in terms of attractions. 

To get there, hop on the MAX line downtown and take it to Washington Park MAX Station.

To take the MAX, which is sort of like a cross between a light rail and a subway, you’ll either buy tickets from the machines on the platform, or tap your credit card at the “tap” machines located on either end of the platform. 

The MAX line drops you at the Oregon Zoo, which we’ve never actually been to, but kids love. 

You can also walk up from the downtown core, but fair warning that it does include a bit of a climb up the hill.

Here’s a good route that takes you up to the rose garden and Japanese Garden. 

As we mentioned, there’s a ton to do and see in Washington Park. Here are our three must-see spots. 

  • The International Rose Test Garden: Portland is known as the City of Roses, which was essentially a marketing campaign decades ago, and this is probably the best place in the city to see them on full display. At least between Memorial Day and Thanksgiving, which is when they are blooming. Thousands of roses of all different colors, shapes, and sizes. We take just about every visitor here. 

  • The Portland Japanese Garden: We love the Portland Japanese Garden, but it is the only of these three spots that isn’t free. Still, it’s a lovely collection of art, plants, and peacefulness. It’s particularly stunning in April/May, when the cherry blossoms are blooming, and October/November, when the Japanese maples littered throughout the grounds turn a stunning shade of “red lipstick” red. We’re members here, and we love bringing people here. The cafe, Umami, is also a fun experience with unique tea service and light bites to enjoy. 

  • The Hoyt Arboretum: This is essentially a tree nursery, where they’ve cultivated a wide variety of different trees from all over the world. We’d make sure to walk a loop that includes a visit to the redwood grove and viewing platform, like this loop
The Portland Japanese Garden in the fall

Practically speaking, there are two ways to explore Washington Park – on foot or using the free park shuttle. If you’re up for hiking (it’s a relatively easy hike), we like this loop, which takes you to all of the spots we listed above. 

Here’s a handy PDF map of the park

If not, the best way to do it is probably going to be the free Washington Park shuttle, which picks up from the Washington Park MAX Station and stops at various spots around the park. 

Northwest 23rd for Dinner and Drinks

After you’re done in Washington Park, we’d recommend heading back down the hill into the Northwest District to finish your afternoon and evening. 

The Northwest District is, as you might imagine, northwest of the core of downtown Portland, across 405, the freeway that runs right through the city. 

It’s one of the more upscale areas in Portland, which is pretty obvious as you’re walking down the leafy stretch of NW 23rd Avenue, the main corridor here. It’s lined with shops, hip restaurants and bars, and tons of trees. 

This also seems like a good place to note that there are a couple of sub-neighborhoods here too, notably the industrial-chic Slabtown, which is at the north end of NW 23rd. 

This is a great place to walk, shop, eat, and drink, which is exactly what you should spend the rest of your day doing. 

We’re going to share a few of our favorite spots in the area, but don’t be surprised if you discover a few of your own as you wander a little bit. 

Eating Dinner in the Northwest District

There are far, far too many places to list here that are worth your time. But we’re going to give you a few options to get you pointed in the right direction. 

You might not know this, but Portland is a pretty outrageously good pizza city. Which was a little surprising to us. There are a bunch of pizza options in the area, and we’d implore you to go for pizza tonight for that reason. 

Go to Escape from New York Pizza for no nonsense NYC-style slices. Life of Pie for woodfired pizzas and more creative toppings (plus great happy hour deals on a margherita pizza). Please Louise is for thin crust pizza and a cozy ambiance. Pizza Thief for their crust and their bar (with a focus on natural wine), but also their focaccia and cannoli. 

Not into pizza? Here are a couple of other options. 

  • Go to Grassa for their Portland-famous handmade pasta.
  • Go to Harlow for gluten free + vegetarian fare.
  • Go to Langbaan for upscale Thai food with a Portland twist.
Drinking in the Northwest District

Here are a few cool spots to grab a drink in the area, depending on what you’re into.

If you’re looking to try one of the best breweries in Portland, head to Breakside at the north end in Slabtown.  

For wine, head to Bar Diane for their rotating selection of wines by the glass and by the bottle (we go here often before Timbers games because it’s a short walk to the stadium). 

Their sister spot, Négociant, is right around the corner and has a nice menu of sandwiches, cheese and meat plates, and a slightly different selection of wines. 

For bourbon, head to Pope House Bourbon Lounge and get a flight or try some local Oregon whiskey. 

For a fun atmosphere, go to McMenamins Rams Head Pub (everyone should probably experience a McMenamins establishment on their first trip to Portland). 

For a nice patio (two, actually) and a good selection of Belgian beers, North 45 is the spot. 

We All Scream for Ice Cream

For a post-dinner and drinks treat, you’ve got a few options on and around NW 23rd. 

First, a special shout out for Salt and Straw, which has a location on NW 23rd that we’ve been to. Salt & Straw is no longer a hip little chain confined to the Portland city limits – they now have locations all over the west coast (and Miami, of all places). 

However, that doesn’t mean their ice cream isn’t delicious. 

The innovative seasonal flavors are where Salt & Straw really shines, and we’d implore you to at least try them when you’re here.

In particular, the berry seasonals in the summertime (Oregon and the broader Pacific Northwest are known for incredible berries) are spectacular. I LOVE the Marionberry Habanero. 

Second is Fifty Licks, which is a few blocks east on NW 21st, and has more of a Portland vibe these days (they were started by a person who moved here to learn how to brew beer, and ended up making ice cream). 

Once again, it’s the seasonal concoctions that really shine here – Alysha recently had a matcha mochi ice cream and a caramelized honey ice cream that she loved. 

Last, and certainly not least, is Kate’s Ice Cream, who recently opened a second location on NW 23rd (summer of 2024). 

Their original location up on Mississippi is within a couple of blocks of where we first lived in Portland, and their 100% gluten free and plant-based ice cream is incredible (they won second place in the dairy free category for the North American Ice Cream Association awards).

We’re fairly certain that if you had us blind taste their plant-based ice cream next to similar flavors full of dairy, we wouldn’t be able to tell the difference. 

Shopping on NW 23rd Avenue

There are a nearly unlimited number of places to shop your little heart out along 23rd, but here are three that we gravitate towards whenever we’re in the area. 

Tender Loving Empire: A cool gift shop full of, well, gifts, most of them locally made and inspired by the Pacific Northwest. Our favorite parts are the apparel section, which has some cool t-shirts and hats, the local food products, and the art. 

Title Nine: Alysha’s favorite outdoor apparel! They’re a women owned and operated company focused on making the best outdoor clothes for women around. Alysha’s favorite hiking pants came from here. 

The Meadow: We actually first discovered the Meadow on Mississippi Ave, and later found out they have stores on 23rd and Hawthorne Blvd now too! It’s a cool store dedicated to salt, bitters, and chocolate. They have an incredible selection of all three from all over the world!

Day 2: The East Side (Southeast + Northeast Portland)

On your second day, take in the contrast between the east and west sides of the city by spending your time exploring the more residential, “neighborhood-y” east side of the river. 

This side of the river is much harder to get around, with a thinner network of public transit to rely on. It makes the most sense to split it into two separate areas – Southeast (which includes Belmont, Hawthorne, and Division) and Northeast (which includes Alberta and Mississippi).  

We’re going to recommend that you start with northeast Portland, and work your way south. You can absolutely do it the other direction if you’d prefer. 

In terms of getting around, your best bets are either using Biketown bikes, Portland’s bike share service with e-bikes for rent around the city, or rideshare apps. It’s fairly walkable within the two areas (e.g. northeast and southeast), but getting between them is a little bit of a pain if you don’t have a car. 

Coffee and Breakfast on Alberta

Northeast Portland is one of the best places to eat and drink in Portland. There are two excellent stretches of places to eat and drink – Alberta and Mississippi – and Alberta is where we’re going to send you to start off this morning. 

Proud Mary: This is a weird one, because it fits for both coffee and brunch in one place. Proud Mary is an Australian coffee brand that set up its US headquarters in Portland years ago, and it’s usually the first place I suggest when people ask me where to find great coffee in Portland. They have great coffee and a fun brunch menu (with great names/descriptions). It’s popular, so be prepared to wait if you show up at 10am on a weekend morning. 

Prince Coffee + Pip’s Original Doughnuts and Chai: Prince is on NE Fremont, which is two main streets (or about 10 blocks) south of Alberta. Prince is harder to get to than Proud Mary, but offers a very useful advantage; it’s right next to our favorite doughnut spot in Portland. Pip’s serves up both fried-to-order mini doughnuts AND a range of amazing chai flavors. Coffee at Prince is a mix of local roasters (including Proud Mary, usually), a rotating mix of international roasters, and great house-made syrups that go into interesting specialty lattes. They’re a couple of blocks away from each other, and make for a great one-two punch to start the day. 

Bialy Bird: We almost always take visitors here if they’re in town on a weekend, because it’s a pop up on NE Killingsworth that is only open on Friday and Saturday mornings (at the time of writing), about a half mile from Proud Mary and the rest of Alberta. A Bialy is similar (though not identical!) to a bagel. It’s sort of like a bagel, but the hole in the middle only got pressed halfway through the bread. It’s also not boiled (only baked), which means the texture is going to be different. Anyway, the point is that Bialy Bird has some really eclectic and unique topping combinations and schmears. The highlight, at least for us, is the sandwiches.  

Tin Shed: If you’re in search of a more traditional brunch experience, complete with lines to match, this is the best option on Alberta. They have a nice outdoor patio too, which is perfect for summer mornings.  

After you’re all fueled up for a day of exploring, we’d head out on a counter-clockwise journey to explore Northeast Portland, starting on Alberta, making your way west and then south from Alberta to Mississippi. 

Exploring NE Alberta Street

Alberta is one of the many stretches of commerce that runs through a residential neighborhood that we think makes Portland special. It’s always a pleasure to bring visitors here and just walk the main stretch, which is lined with shops, places to eat and drink, and some solid people watching. 

Here are a few of our favorite spots (other than Proud Mary and Tin Shed, which we mentioned above). 

  • Crafty Wonderland: A great arts and crafts store with offerings from local artists. They put on an annual winter wonderland show at the Convention Center, which is where we get a lot of our Christmas gifts. 

  • Ecovibe: A very hip-feeling home goods store with plenty of plants. 

  • Roseline Coffee: Another of Portland’s local coffee spots, Roseline is worth stopping at if you need another pick me up. 

  • Revive Athletics: A second hand athleticwear store that Alysha really likes to pop into. 

  • Alberta Cooperative Grocery: Probably our favorite grocery store in Portland! We moved to the other side of the city, and now anytime we’re up on Alberta we make a detour to stop here. 

  • Citizen Ruth: Another great gift shop, particularly their stickers and greeting cards, which are usually creative takes on current events / pop culture. I got my brother a Roy Kent mug (of Ted Lasso fame) for Christmas a few years ago. 

Peninsula Park

Peninsula Park is a bit of a detour on the way from Alberta to Mississippi. However, it’s worth the detour for the Rose Garden, which is the oldest in Portland (despite its more famous counterpart in Washington Park getting all the fanfare). 

Worth noting that the roses bloom from roughly June through October, and it’s probably not worth the detour outside of those months. 

Mississippi Avenue 

When we first moved to Portland, we lived right off of Mississippi Avenue in Northeast Portland, which is one of our favorite stretches in the city. 

However, there is one important piece of historical context to think about here. 

Portland is a very white city (which was a little jarring coming from Seattle and the Bay Area, where there are large non-white populations). Which, as I learned recently at the Oregon Historical Society, was a very intentional choice made by Oregon at the state’s founding. 

The area around Mississippi Avenue, which today is full of hip bars and restaurants, is a historically Black part of the city. You would barely know that walking through today, which is why we’re bringing it up. 

We love all of the great places to eat, drink, and shop along Mississippi, but that development has come at a cost, as rising rents have pushed primarily Black residents that called this area home further east in search of affordable places to live. 

In reality, the story is much darker than that, but we don’t have room (or knowledge, honestly) to get into it here. 

Instead, we’d point you here to learn about the discriminatory history of policies around housing in Portland, and this piece on the changes the neighborhood has seen through the eyes of elementary school students. 

We’re obviously not saying don’t go to Mississippi Avenue – it’s here in this itinerary for a reason – but to keep that context in mind as you’re enjoying the places here. 

With that out of the way, let’s talk about Mississippi Avenue today. 

There are two things we think you should definitely do while you’re here – eat at the food carts at Prost! (which have been recently featured on Somebody Feed Phil, our favorite food show right now) and grab a drink at one of the local breweries on this stretch

One thing every single person who comes to Portland should do on their first trip is eat at a food cart. It’s a unique aspect of Portland’s culture, and is partially responsible (in my opinion) for the amazing food scene in Portland by allowing for low cost innovation and risk taking. 

In terms of the food carts, you have plenty of options in the little pod at the corner of Skidmore and Mississippi. Here the highlights:

  • The most famous is probably Matt’s BBQ, which routinely has a line at lunchtime and sells out most days. They do Texas-style barbecue, and are known for ribs, brisket, and burnt ends. 

  • Our personal favorite is DesiPDX, which is Indian cuisine featuring fresh Pacific Northwest ingredients. Their cardamom chai chicken is in our top three favorite dishes in Portland. It’s spectacular. Plus, it’s all gluten free, and they have plenty of vegetarian and vegan options. They also have a newer restaurant nearby called Masala Lab, which is worth a visit on a later trip (get the amazing hash with housemade bacon). 
The cardamom chai chicken at Desi PDX
A sandwich at Matt’s BBQ

From there, walk south down Mississippi. 

There are tons of places to shop here, like another location of the Meadow (the salt/chocolate/bitters store where we get all of our gifts around the holidays) and the very cool Rebuilding Center, which is a nonprofit dedicated to reducing waste by taking broken stuff, fixing it up, and selling it at affordable prices. 

If, somehow, after lunch, you’re up for something sweet, head to either Blue Star Donuts (Portland’s original $5 hipster donut) or Kate’s Ice Cream (plant-based and gluten free ice cream), which are two of our favorites. 

The other thing you should do here is grab a cold locally-brewed beer. Stormbreaker, which has a lovely patio and live music on weekend evenings, is at the southern end of Mississippi, and is a fitting last stop on your mini tour-de-Mississippi-Ave. 

After that, your next stop is Hawthorne and Belmont in Southeast Portland. Unfortunately, there’s no real good way to get there other than driving. If you don’t have a car, you’ll need to take a rideshare. 

We’d take it to Cubo (here on Google Maps), which is the western end of the cool stretch of Hawthorne Blvd. 

An Afternoon and Evening in Southeast Portland: Hawthorne and Belmont

After your time in Northeast Portland, head directly south to explore the areas around Hawthorne and Belmont, two really nice stretches full of bars, restaurants, shops, and more. You can make a nice little loop, stopping for dinner, drinks, and shopping along the way. 

Hawthorne is known for vintage shopping, which we’re not really into, but my hip cousin Aubrie is all about it and loves browsing on Hawthorne. 

The stretch of these two streets to focus on is roughly between 30th and 39th (aka SE Cesar Chavez Blvd), so a loop might look a little something like this

If you have the time and the energy, it’s worth venturing out to Mount Tabor, the cinder cone that looms over this part of Portland to the east. It’s now a park, and it’s one of the best green spaces in Portland. 

Portland is a city of cinder cones – which are formed by volcanic activity – with Mount Tabor being the most famous of the bunch. 

You’ll often find us up here with the dog on warm summer days walking this loop, which is one of our favorite hikes in Portland.

There are some great views of Portland from the top of the stairs near Reservoir Number 5, and some nice views of Hood on the east side of the park. 

Spoiler: We have you heading to Division Street for your third night, so we’re sticking to Belmont and Hawthorne here. There’s still plenty to do, see, eat, and drink, don’t worry!

For Dinner: We love Taquería Los Puñales and their thick tortillas make the perfect base for their stewed fillings – guisados – and they also make the best fresh-fried tortilla chips. Great aguas frescas too! 

For Drinks: If cocktails are what you’re in the mood for, head to the Sapphire Hotel (do not pass go, do not collect $200) for a swanky yet down-to-earth vibe and creative cocktails (plus, a nice food menu and good happy hour deals). For beer, go to Belmont Station on Stark, which is a neighborhood institution. If you want wine, go to Nil for their rotating glass pours that are focused on natural wines from all over the world. 

Day 3: The Columbia River Gorge, the Central Eastside, and Division

On your third day in Portland, it’s worth leaving the city for a morning spent in the Columbia River Gorge, which is our go-to destination both for a quick weekend hike, and to take visitors from out of town to “ooh” and “ahh” over the many, many waterfalls in the Gorge. 

Take a Day Trip to the Columbia River Gorge

The best way to do this is definitely to have a car so you have more flexibility (and if you do have a car, you should read our guide to planning a day trip to the Columbia River Gorge), but we also don’t think you should rent a car if you flew in from out of town, so we have two options for you: a guided tour, and using public transportation.

There are obviously pros and cons to each approach, and it really comes down to cost vs. convenience and flexibility. 

Doing a guided day trip means that you basically just get to sit back and relax as you are whisked around from waterfall hike to waterfall hike. It also includes transportation to and from Portland, which is nice. 

Doing a day trip using public transportation is going to be more affordable and means that you have a little more flexibility in itinerary and timing. But you do have to figure out how to get to the pickup point, which is a little bit of a nightmare. 

However, given the available options for public transportation, we’d recommend a guided tour if you don’t have a car. 

Unfortunately, the public transportation options still kind of require you to have a car (or to take a long Lyft ride). They essentially mean you either have to get out to a parking lot in the Gorge that doesn’t have a public transit connection OR limit your trip to Multnomah Falls (which isn’t how we’d do it!). 

For full transparency so you can see what we mean, the two options are the Columbia Gorge Express (takes you from Gateway Transit Center to Multnomah) and the Sasquatch Shuttle (nice loop, but requires you to get to Bridal Veil Falls in the Gorge). 

Here are the two guided tours that stand out to us – both are owned and operated by local Oregonians (which is key!), get great reviews, and follow an itinerary that makes sense to us.

Half-Day Columbia River Gorge and Waterfall Hiking Tour (4 hours): This tour meets in Portland (in the Central Eastside) and heads out to the Gorge straight to Multnomah Falls, the most impressive waterfall in Oregon. From there, it makes a few different stops that we really like – great views from the Vista House and Women’s Forum Viewpoint, and two additional waterfalls – before bringing you right back to Portland. Is it a perfect itinerary to us? Probably not, but it hits 90% of the stops we’d make on a self-guided tour!

Hike and Bike Tour to Columbia River Gorge Waterfalls (5 hours): The main difference between this tour and the first tour above is the fact that, in this tour, you’re getting to see parts of the Gorge on a bike! Which is both unique and VERY Portland. It’s a very similar list of stops, you just break them up on a bike rather than in a van. 

If you choose either of these tours, we’d recommend the morning tour that leaves at 8:30am, which will have you back in Portland around lunchtime. You’ll get dropped back in the Central Eastside, which is a perfect place to grab lunch. 

Lunch in the Central Eastside

The Central Eastside is the area directly across the Willamette River from downtown, and its roots are very industrial, with big warehouses along the railroad tracks. 

However, in recent years, there has been a noticeable effort to reinvigorate the Central Eastside with cultural events like the Portland Night Market and remodeled warehouses being used for office and commercial space. 

The point is that there is a good mix of places to eat in the Central Eastside. Here are a few that we like. 

  • Hawthorne Asylum: This is one of our favorite – and the most developed – food cart pods in Portland. There are 15-20 carts here, and a big seating area to enjoy their food (with fire pits in the cooler months!). We come here for Your Side Chicks, a cart making excellent gluten free fried chicken (his whole thing is that the chicken is fresh, not frozen, which means it’s much juicier), but you also can’t go wrong with the dumplings from Pelmeni Pelmeni

  • Grassa: If you missed their handmade pasta over on NW 23rd, they also have a location here. They serve a range of pasta dishes like carbonara and squid ink linguine, along with sides and drinks. 

  • Lardo: One of the most famous sandwiches in Portland! This is the place to go for a sandwich and a beer post-hike.

  • Dos Hermanos Bakery: One of the best bakeries in Portland, you see Dos Hermanos a lot at other coffee shops and cafes around Portland since they have a robust wholesale business. They also have a cafe in the Central Eastside where you can get sandwiches made on their baguettes, along with all of their pastries and baked goods. 

  • Afuri: A ramen spot hailing from Japan (fun fact: Portland is their only location outside of Japan!) specializing in crafting dishes with local, seasonal ingredients.

  • Obon Shokudo: Plant-based Japanese comfort food. Think onigiri, udon, and curries. A fan favorite among our vegan friends, but Aysha also loves it.

  • Shalom Y’all: Some of the best Mediterranean food in Portland. Don’t miss the Halloumi, pita delivered straight to your table from the wood fired oven, and fun cocktails (the Turkish Delight Slushy is perfection on a warm summer day).

Exploring the Central Eastside

The Central Eastside is probably the single neighborhood where we find ourselves most often in Portland. Which probably has something to do with the fact that we live nearby, but still. There’s a lot going on!

After lunch, it’s worth spending a second walking around and exploring this part of the city. 

  • Revolution Hall: If you’re looking for a great rooftop patio where you can grab a drink with a view, this is our favorite spot in Portland. It’s an old school that has been turned into a concert venue on the ground floor with a rooftop patio. It’s very vibey, but there’s something special about sitting up there with a view of both downtown and Mount Hood on a warm sunny day. 

  • Smith Teamaker: Perhaps Alysha’s single favorite place in all of Portland? If you’re a tea lover, this is basically a must-stop. Their flagship here in the Central Eastside is where they pack all of the tea, and as soon as you’re within half a block you get wafting smells of whatever tea they happen to be packing that day. They have a vast menu of teas, including tea lattes and tea flights. We like the nitro chai, which is very unique (there’s no dairy, but the nitro gives it that creamy mouthfeel). It’s also a good place to grab edible souvenirs (read: tea) to take home. 

  • Sunflower Sake: Another of our very favorite spots in Portland, Sunflower Sake is everything we love about Portland’s food and drink scene packed into one cozy high-ceilinged, industrial-chic space. Nina, the proprietor here, is passionate about many things, and they all come together in this space dedicated primarily to the world of sake. Which we knew next to nothing about before making semi-regular visits to Sunflower to introduce visiting friends and family to sake. It’s a one-person show, and Nina’s passion shines through every time I talk to her (I just like listening to passionate people talk about whatever thing they’re passionate about). 

  • Cowbell Cheese: Another gem in the Central Eastside! Cowbell is a lovely little cheese shop tucked into what must have been a garage at one point. They have a rotating selection of cheeses from small producers all over the world, and the staff are super knowledgeable and able to help you find something you like. They also have some fun imported products for sale, and make a mean sandwich. 

  • Schilling Cider: If you didn’t already know, the Pacific Northwest is the center of the world’s apple production. Specifically, Washington State and the area around Wenatchee, but northern Oregon produces a fair amount of apples too. Schilling – which Matt knows from his days living in Seattle, where they started – has a cider bar with 50+ different hard ciders on tap, and it’s a great place to either get acquainted with the world of cider, or for cider lovers to try some local options. 

  • Portland Syrups: We really enjoy Portland Syrups, which are basically flavored syrups that you dilute with sparkling water and/or alcohol to create your own soda-ish concoctions (and avoid buying plastic bottles of soda or flavored sparkling water when paired with something like a Sodastream!). They’re born and bred – and still produce everything – in Portland. They have a brick and mortar location in Portland where you can buy a wide range of their flavors (and they’re generous with letting you try them here). Another good souvenir to bring home. 

  • Cargo: This store is super fun! Situated in a classic Central Eastside warehouse space, it’s basically an upgraded version of World Market, with knick knacks, cards, clothing, textiles, and more from all over the world. It is huge and covers two floors, so plan to spend some time wandering.

Division Street

We saved the best for last here, and we’re more than a little biased because we live within walking distance of Division. Close out your time in Portland with what is our single favorite stretch in the city – Division Street between SE 20th Ave and SE 50th Ave. 

Here are some of our favorite spots to eat, drink, and be merry along Division. 

Alysha also really loves Artifact, a consignment shop on Division that has an eclectic collection of recycled clothes, furniture, art, and more.

However, unlike other consignment stores where it’s a mix of more modern items and items from your grandma’s wardrobe, everything here is modern!

For Dinner

There are an endless number of great places to eat and drink along Division, so we’re having to do some picking and choosing here. 

  • Rangoon Bistro: One of our favorite restaurants in Portland! They are a classic food cart to full restaurant (and now, two!) story, and it’s easy to see why. Their food is fantastic. Particularly the fried chicken and Laphet salad. 

  • Magna Kusina: A block off of Division in the Clinton Triangle, this place started as a pop up and has quickly become one of the most popular places to eat in the neighborhood. It’s Filipino food, and it’s a mix of street food, small plates, noodle dishes, and bigger proteins. It’s a great introduction into Filipino food, if that’s something you’ve never tried before. They’ve begun expanding into different pop ups featuring their chef friends, which is fun. Make a reservation! 

  • Kashiwagi: We walked by this tiny spot tucked into the back corner of a nondescript parking lot all the time before finally realizing that it was a very popular, very highly rated bento and sushi place. They have good lunch specials, and are very affordable. 

  • The Turning Peel: Excellent sourdough Neapolitan pizza served in a classic Portland Craftsman style home with an even cuter patio. Do not miss the tiramisu when they have it!

  • Ava Gene’s: A little more upscale here, they serve Roman food made with fresh Pacific Northwest fruits, veggies, meats, and cheeses.

  • Oma’s Hideaway: While everyone still mourns the loss of Pok Pok, a Division Street institution that closed in 2020, Oma’s fills the void with incredible hawker food from Singapore and Malaysia. The roti, a handmade flaky Malaysian flatbread, served with parsnip & squash curry hits the spot every time. Plan to share so you can try a bunch of dishes, and be ready for spice.
Fried chicken (gluten free) at Rangoon Bistro
Great pizza (not GF) at Turning Peel
Dinner at Magna in Portland
For Sweets

For a post-dinner treat, there are two places along Division that really stand out from the crowd. 

  • Lauretta Jean’s: When was the last time you had pie that wasn’t on a holiday? It doesn’t happen often for us, and walking into Lauretta Jean’s is heaven for pie lovers. They sell pies by the slice and full pies with a wide range of flavors, including rotating fruit and chocolate options. You really can’t go wrong, but salted honey and coconut cream are Alysha’s favorites.

  • Pinolo Gelato: Easily the best gelato in Portland, and perhaps the best gelato on the west coast (?). They source ingredients from Italy, and it shows (their pistachio gelato is a darker brown color, not a fluorescent green, which is a sign that it’s made with real pistachios without colorings). It was started by an Italian-American born in Pisa, and it’s legit really, really good. 
For Drinks
  • Division Wine: Our favorite wine bar in the neighborhood, the selection is big and the prices are (relatively) small here. Plus, the staff are extremely helpful. The last time we were here, we had friends from California in tow who had a specific view of chardonnay that leaned into oak, which is not how it’s made in the Willamette Valley. We asked our server to help us find some Chardonnay that would change their minds, and he delivered! Get a flight, which features surprisingly hefty pours. They usually have several bottles open that aren’t on the menu, so ask your server for help!

  • Imperial Bottle Shop & Taproom: A spot for beer lovers to try beer from multiple breweries around Oregon. They have an outdoor patio, too, and it’s a great place to spend a warm summer evening with friends. Lots of bottles and cans to choose from, too. 

  • Little Beast Brewing: Portland’s craft beer scene is famously good, and Little Beast’s Beer Garden on Division is a good place to experience it. They have a nice (covered and heated in the winter and spring) outdoor patio, a food truck and live music on weekends, and an eclectic range of beer (including too many different IPAs to count, several sours, and rotating seasonal beers). 
A flight at Division Wines in Portland (LOOK AT THOSE POURS!)

What to Do with Less Time in Portland

Less time to spend in Portland? We have entire guides dedicated to spending one day in Portland and 2 days in Portland, where we’ve picked and chosen our favorites from this itinerary and condensed it into a shorter time frame. 

What to Do with More Time in Portland

If you have more time in Portland, our biggest recommendation is to plan another day trip to explore outside of the city. 

Again, one of our favorite things about Portland is the fact that we’re 90 minutes from both the coast and the mountains. 

If you’re blessed with some extra time, you have the opportunity to experience all that sheer natural beauty, from snow-capped peaks and never ending evergreen forests to rugged sea stacks and pristine sand beaches for yourself. 

…Eat (and Drink) More

Most of the time, when people come to town to visit, we follow some version of this itinerary. Which usually involves a lot of eating and drinking with some breaks for digestion and other attractions in between. 

There is an absurd amount of good food to eat in Portland, and you could spend weeks going from place to place to try and check them all off your list (we know because that’s basically what we do!). 

The sheer amount of innovation and people trying cool stuff is one of our favorite things about the city. 

Remember, most of the places listed above aren’t necessarily gluten free (though they lean that way given Matt’s dietary needs). If you need to eat gluten free, you should head over to our guide to the best gluten free restaurants in Portland

Catch a Portland Timbers (Or Thorns!) Game

Portland is home to three professional sports franchises – the Portland Timbers, the Portland Thorns (NWSL), and the Portland Trail Blazers. 

Matt is a big soccer nerd (his favorite stat – as a goalkeeper by training – is PSxG), and so we’re partial to Timbers and Thorns games, which are at Providence Park right in the middle of the city. 

The other cool part about Providence Park is that it’s a soccer-specific stadium, rather than being an NFL stadium that is retrofitted to hold a soccer game. 

Check the schedule for the Timbers and the Thorns for your trip dates to see if there’s a game in town. 

The Blazers – Portland’s NBA team – are a little bit of a mess right now (I’m writing this during the height of the Dame drama), but if you’re into basketball, Blazers games are also a good time. 

Stop By the Oregon Historical Society

While Portland doesn’t really have a world class museum, it does have a unique museum right in downtown Portland that covers the history of Oregon. It’s called the Oregon Historical Society, and I only made it there recently for the first time and was blown away at how comprehensive it is. 

Here’s the thing about Oregon: it may be one of the most progressive states in the Union today, but it.. uh… wasn’t when it was founded.

The thing I appreciated about the Oregon Historical Society is that it covers the history of Oregon from soup to nuts AND doesn’t pull punches.

And, for some of the more scandalous claims (like the fact that Oregon explicitly excluded all non-white people at its founding), it brought the receipts with pictures of original documents and quotes from said documents. 

The best permanent exhibit is the “Experience Oregon” on the top floor. It’s worth catching the video at the beginning, and then you’ll embark on a journey that takes you through the history of the state, from the time where humans weren’t here at all until almost the present day. 

You’ll learn about the people that lived here before Lewis and Clark showed up, the first European settlers and how their ideas about land ownership clashed with the indigenous tribes here, and the formation and evolution of the state. 

It’s well worth an hour or so of your time to understand the context that Portland and Oregon as a whole exist in today. 

It’s $10 – free for Multnomah County residents – and there are reduced prices for kids. 

Hike to Pittock Mansion

We did our best to find a way to include the hike to Pittock Mansion in the main itinerary above, but ultimately it came down to choosing between a day trip and this hike, and we think the Columbia River Gorge (or another day trip) is ultimately more worth it for visitors. 

The view from Pittock Mansion is the best view of the city, we think, with a view of downtown, “Big Pink” (that’s the big pink office building downtown), Providence Park, and the snowy peak of Mount Hood in the distance. 

The hike starts from Lower Macleay Park in Northwest Portland, and starts with a gentle walk along the creek through the woods before it gets a little more difficult, climbing through a fern-laden forest up to Pittock Mansion. 

Pittock Mansion is where one of the original Portland moguls made his home after he made a fortune in the timber industry. 

Seeing rich people’s homes isn’t really our thing, so we’ve never actually been inside (we’ve also been told it’s not really worth it by people who have done it), but the view from the viewpoint just outside is well worth the couple of miles of climbing to get there. 

We have an entire guide to hiking to Pittock Mansion, which you should read for more details on how to actually make it happen and what to expect. 

Head Out to the Oregon Coast

The Oregon Coast is another one of our favorite day trips, but it’s a little harder to get to from Portland without a car.

There are two main Oregon Coast destinations that we think make for a nice day trip, and you can actually do both and form a loop that starts and ends in Portland. Those two destinations are Astoria and Cannon Beach. 

Unfortunately, there is essentially zero public transit to speak of between Portland and either of those places. If you don’t have a car and you want to head out to the coast, your only option is to do a guided tour. 

Obviously, we have a car since we live here, but we combed through the tour companies and options to see if there were any tours to the coast that we’d recommend. 

If we were going to do a guided tour that took us out to the Oregon Coast from Portland, this is the tour we’d choose

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