A Weekend in Portland: How to Spend 2 Days in Portland

Y’all, Portland is one of the best cities in the country for a weekend trip. It’s a big enough city that there’s plenty to do and see to keep you busy for a couple of days, but it’s not so big (looking at you, New York City) that it’s nearly impossible to even make a dent in.

Portland has a couple of things going for it that make it a really special place to explore.

First and foremost, it’s an incredible food city. There’s something about the culture of food carts – which are very prominent in Portland – that has created this unique atmosphere that is the perfect breeding ground for innovation.

Second is the great green spaces within the city limits. In particular, we love Washington Park, which is near the top of the list of the best urban parks in the country (don’t worry, you’ll find it in the guide below!).

With 2 days in Portland, we think you can see some of the highlights, eat and drink your heart out, and walk away with a list of even more things to do, see, eat, and drink the next time you’re here. If you’re anything like we were before moving here, you might even book your next trip here on your way home from this one.

In this guide, we’re going to start off with some logistics – when to visit, where to stay, and how to get around – before we dive deep into EXACTLY how we’d spend a weekend in Portland, Oregon. Including, of course, what to eat and drink. Because, as you’ll soon see for yourself, Portland is an underrated food city (though not for long – the secret is out!).

Sound good to you? Let’s get into it and help you plan an amazing trip to Portland.

Our credentials: After nearly 9 trips to Portland over the course of a decade, and plenty of “oh, now’s not the right time, maybe next year” conversations, we finally made the decision to move to Portland permanently. We’ve seen the city as tourists in all of its different seasons. And now we lived in Portland, which means we’ve seen it from a slightly different angle.

Disclaimer: Some of the links in this post, like hotel and vacation rental 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 absolutely never recommend something to you that we don’t stand behind 100%.

Why Listen to Us When You’re Planning Your Weekend Trip to Portland?

We have a somewhat unique perspective on Portland. It has been our favorite city on the west coast for almost a decade at this point (and even then, we were a little late to the party). 

We’ve visited as tourists more than seven times over that time period. Then, we finally made the move to Portland happen, and we’ve also seen the city as residents. 

Having lived in other places, we know that living somewhere long term sometimes means you take things for granted (for example, the amazing parks inside the city limits), and having a visitor’s perspective and mindset from our first several trips to Portland helps us appreciate and remember those small things that make Portland a special place. 

We’re not really locals just yet – though we’re learning more and more about the City of Roses with every passing day – but we do live here and spend a lot of time exploring the city and surrounding areas. 

Is 2 Days in Portland Enough Time?

Portland is a relatively small city, which means that we think you actually can do most of the highlights in Portland in 2 days.

If you spend your time wisely, you can explore downtown Portland, spend some time in the amazing green spaces that make Portland special, and explore the cool neighborhoods on the hipper, more residential east side of the river.

However, we also think that part of what makes Portland special is everything just outside the city limits – the Columbia River Gorge, Hood River, and the Oregon Coast to name a few. With 2 days, you probably don’t have time for a day trip from Portland to make it out to some of those special places. 

To summarize, you’ll get a great overview of the city, but you’ll miss out on those places just outside the city, which you’ll have to save for a return trip. 

The Best Time to Visit Portland

Chances are, if you’re on this page, you already have some idea of when you want to visit Portland. In this section, we’ll talk through what to expect in each season, along with some of the pros and cons of visiting in each season. 

Summer in Portland is MAGIC

Summer is, without a doubt, the best time to visit Portland. You’ll have long, sunny days to maximize the amount of daylight for exploring, and it’s the least wet time to be in Portland. The sun rises before 6:00am, and sets between 9:30 and 10:00pm. 

Summer in the Pacific Northwest generally means July 5th through Labor Day (for some reason, 70% of the time it’s cloudy on July 4th).

Portland really comes alive during the summer, with all sorts of street fairs and outdoor events that pop up to make the most of the warm, dry weather. 

What’s the catch? Higher demand means more tourists and higher prices. There will be more competition for flights and hotels, so you’ll want to book as early as reasonably possible. 

The other consideration for a summer visit is the fact that, increasingly in recent years, it can get very hot in Portland. If you’re coming from the midwest or east coast, I can hear you scoffing right now. But the difference between your city and Portland is that the infrastructure in Portland is not meant to experience that heat.

Just 5 years ago, it was fairly uncommon to have days over 100 degrees. It would happen, sure, a couple of times a year, but not for extended periods. 

This summer, there were at least four different stretches of three to four days each where it was over 98 degrees. If you’re visiting in the summer, make sure to have A/C at your accommodations! We don’t have air conditioning in our house, and it’s miserable when it’s that hot outside. 

A related thing to think about is smoke from wildfires in the western United States. Again, increasingly so due to climate change, Portland finds itself blanketed in a thick bank of smoke from nearby wildfires a couple of times during the summer and early fall. It’s impossible to predict, and can change in a matter of days, but it’s something to keep an eye on. 

Fall in Portland is a Good Balance

Fall is, in our opinion, a great option for visiting Portland. You’ll get to experience many of the same benefits as summer – the dry, warm weather – without the drawbacks like crowds and extreme heat. 

Plus, while it’s not at the same level as it is in the mountains, there is some nice fall color to be had in Portland. 

We’d recommend timing your visit for early September (after Labor Day) for the best weather. 

Winter and Spring in Portland Can Be Dreary

Hiking just outside of Portland in the winter – it’s not so bad!

We’re going to group these together, because they’re largely the same. Before moving here, we had actually spent a fair amount of time in Portland between January and April, partially to make sure Alysha (who was born and raised in California) could handle the gray. 

The first thing to know about visiting in the winter is that when people say “it rains a lot,” the reality is a little more complicated than it seems. 

Yes, it rains. A lot. From roughly November to April or so.

But “a lot” is more about the frequency than the quantity. The day-to-day experience is more of a constant light drizzle than a huge downpour. 

However, that means that doing things outside is a little less enjoyable. If you want to explore Portland and all its lovely green spaces, winter and spring aren’t going to be great (prepare to be muddy and damp). 

If you’re content exploring the food scene, Portland’s amazing coffee shops, and spending a little more time indoors, then winter and spring are definitely going to be a more affordable time to visit Portland. 

Where to Stay for a Weekend in Portland

Since you’ve only got two days, you’re going to want to immediately narrow your search to the downtown core so that you’re not having to trek back and forth between the place you’re staying and your destination. 

By the way, we have an entire guide dedicated to the best places to stay in Portland, which has far more detail than the abbreviated version below. If you want to go deeper, read that.

There are basically two areas we’d recommend that fit that description: Downtown Portland and the Central Eastside (a specific part of Southeast Portland).

A Quick Note About Airbnb in Portland

First of all, we used to love Airbnb, especially because we often need a kitchen when we travel because Matt has Celiac Disease, which means eating out can be tricky (that’s putting it lightly). 

However, between the fact that we’re in the midst of a full-fledged housing crisis in every major city on the west coast, the fact that Airbnb has gone from someone renting an extra room to corporations building huge vacation rental empires, and the sometimes exorbitant cleaning fees (even though you often have to do the dishes and the laundry yourself) we find ourselves having a harder time recommending it. 

We’ve fallen back in love with hotels as they’ve stepped up their game, and the prices of Airbnb have risen so that they’re actually more expensive (unless you’re traveling with a big group). 

However, we know that you might prefer a little more space or a different experience than staying downtown, and there are pockets of the city without any hotels to speak of. So here’s our recommendation: for the best experience, stay in an Airbnb where the owner lives onsite, like a backyard bungalow or a studio over the garage. 

In our experience, those stays – where you’re able to make a small connection with the host and get some recommendations from them – are where Airbnb is at its best. 

Also, the best places to find an Airbnb in Portland are going to be on the east side of the river, in southeast Portland and northeast Portland (near Alberta and Mississippi). Don’t stay in an Airbnb downtown or in the Pearl – it won’t be meaningfully different from a hotel stay. 

Staying in Downtown Portland

Downtown Portland is the most convenient place to stay if you’re trying to see the best of Portland in two days. You’ll have full access to the downtown core, you’ll be able to get up to Washington Park fairly easily, and you’ll be able to hop across the river to the eastside too. It’s central, it’s well connected, and it’s practical. 

The downside is that downtown Portland isn’t particularly charming and doesn’t have the best food and drink scene, but that’s probably okay for a couple of days (if you’re looking for charm, consider staying in the Northwest District / Slabtown near 23rd Avenue). 

In terms of specific hotel recommendations, we have a couple. We haven’t stayed at this particular location, but we’ve stayed at other Ace Hotel locations (in Seattle and NYC) and liked them both, so we’d definitely consider the Ace Hotel Portland. It’s a block or two away from Powell’s City of Books and some of the best food and coffee options in downtown Portland. 

The Hyatt Centric is in the same vicinity as the Ace, and is essentially brand new. It’s part of Hyatt’s relatively new hip, trendy, modern hotel brand that takes inspiration from brands like CitizenM (who we love and have stayed at multiple times, but they don’t have a Portland option…yet). 

Staying on the Central Eastside

The Central Eastside is a specific part of Southeast Portland that is a little less practical in terms of location and public transit connections, but is closer to the absurdly good food and drink scene on the east side of the Willamette River. 

As you move east from the river, Portland gets progressively more residential. The Central Eastside skews more industrial than residential, but it’s as close as it gets to stretches like Hawthorne, Division, and Belmont, which are packed full of great food and drinks. 

It also happens to be home to some of the coolest hotels in Portland, which is an added bonus.

First of all, if you’re looking for a unique stay to match the city’s vibe, stay at Tiny Digs Hotel, which is a hotel made up of cool tiny homes! It’s a bit further out, but a few of our favorite spots in Portland (like Mikiko Mochi Donuts, Güero, and Pollo Norte) are within walking distance.

And can you really say no to spending a couple of nights experiencing tiny home living while you’re visiting Portland? 

If you’re on a budget, we’d look at the Kex Hotel and Lolo Pass, two affordable-but-stylish options in the area. Both are sort of hotel/hostel hybrids, which means you can get what is essentially a boutique hotel room at a more affordable price. 

We stayed at the Jupiter NEXT Hotel for our last trip before moving here, and it’s legit. It’s not the cheapest option, but the rooms are big, clean, and comfortable, and some rooms have great views of Portland.

Our room at the Jupiter NEXT in Portland

The service was also fantastic, and we chatted with the hosts at the front desk just about every time we walked by. Highly recommended!

Getting Around Portland

First of all – and this is important – we would definitely NOT recommend renting a car if you’re just here in Portland for a weekend

Parking can be difficult, and 95% of the time you’re going to want to leave your car parked at your hotel anyway. 

We’ve specifically designed this Portland weekend itinerary so that you don’t need a car to do it. 

If you’re driving to Portland, then we’d recommend leaving your car parked where you’re staying for most of your trip. 

If Portland is a jumping off point for a road trip – like an Oregon road trip or a road trip on the Oregon Coast – we’d say the same thing. If you can, rent a car on your way out of town to save money on parking fees!

Using Public Transportation in Portland

Look, we love a good public transportation system. I got laughed at in London when my answer to “what’s your favorite thing about London?” was “the great public transportation network.”

Portland is no London. Let’s be super clear on that. However, it is relatively easy to get around using public transportation, and is getting better over time. 

There are basically three forms of public transportation in Portland – the MAX (light rail), the Portland Streetcar (also sort of light rail), and the TriMet bus system. 

All three are useful, and also happen to be relatively easy to use. 

Buses in Portland

Buses in Portland are run by TriMet, and are generally a good way of getting around. 

For buses in Portland, all you need to do to pay is tap your credit card when you get on. The best part? The system caps you at $5 a day AS LONG AS you use the same credit / debit card to tap every time you ride (you can only tap one card per person). Each ride costs $2.50, and includes transfers for two and a half hours. 

In general, if you need to go diagonal (e.g. northwest), you’ll need to make a transfer. Most buses run either north/south or east/west. 

The MAX 

The MAX is Portland’s light rail. Its biggest purpose is to connect the suburbs immediately around Portland with the core of the city, which means it’s not going to be SUPER useful for your visit to Portland. 

The most useful line for your purposes is either going to be the red line from the Airport to Downtown, or the Red/Blue lines from downtown to Washington Park (which we’d recommend for getting from Downtown Portland to Washington Park on day 1 above). 

To ride, you can either tap your credit card at the HOP Fastpass reader on the platform, or buy tickets from the automated machines on each platform. Again, it’s $2.50 a ride (good for two and a half hours) with a daily cap of $5 AS LONG AS you use the same credit / debit card to tap.

Trains come relatively frequently – every 15 minutes or less – which is nice. 

The Portland Streetcar

The Portland Streetcar is the first modern streetcar service (what constitutes a “modern” streetcar, you ask? Not a clue.) in the country, making its first ride in 2001. Since then, it has been consistently expanded, adding more tracks every few years.

For your purposes, it’s probably most useful to get from downtown to the PSU Farmers Market or Northwest District, though it also runs to the Convention Center, MODA Center (where the Blazers play), and along the main corridor in the Central Eastside (if you’re staying in the Central Eastside, it’s a good option for getting downtown, though there are also multiple bus lines too).  

The Portland Streetcar is not operated by TriMet, but the fares are interchangeable, so you can transfer from bus or MAX to Streetcar, and vice versa. However, if you’re starting with a ride on the Streetcar, you’ll need to purchase a specific fare for it to be valid on TriMet services.

It’s called the “TriMet 2.5 hour” and costs $2.50. Otherwise, a single ride on the Streetcar only is $2. 

Cycling in Portland

Portland is a fairly bike-friendly city, with dedicated streets for cycling with limited traffic (especially on the more residential eastside). 

There are also a few scenic rides within the city limits – like the Eastbank Esplanade, which boasts great views of the Portland skyline – that are worth a few hours of your time (though probably on your next visit). 

The easiest way to rent a bike in Portland is through Biketown, which are the orange electric bikes you’ll see all over the city. If you’re a tourist (as opposed to someone who buys an annual pass, which is only worth it if you’re a frequent rider), it’s $1 to unlock a bike, and $0.20 a minute. 

For what it’s worth, we often use this service. The easiest way to do it is to pick up and drop off at dedicated Biketown platforms. Here’s a guide on how to use Biketown bikes

Your other option is to rent bikes through a bike shop or bike rental company, which are largely concentrated along the river (because that’s where most people ride them). Cycle Portland is probably your best bet given the location. 

A Perfect Weekend in Portland: A Complete Guide to Spending 2 Days in Portland, Oregon

And now, the main event! We’re about ready to get into the meat of how to plan an amazing weekend trip to Portland. 

Day 1: The West Side of the River (Downtown and Northwest)

On your first day in Portland, spend your time on the west side of the river, exploring Washington Park and the Northwest District before heading east into Downtown Portland and the Pearl District. 

I’m going to assume this is a Saturday for most people, which means you should definitely stop at the PSU Farmers Market  (info here) for breakfast and walk from there along the river to the Portland Saturday Market (info here).

Both of those events take place on Saturdays only. If you’re not in town on a Saturday, head from coffee in Downtown Portland up to Washington Park, and then continue the itinerary as written. 

Coffee in Downtown Portland

Spoiler alert. Portland is a legendary coffee city. Whether you’re into specialty coffee and trying the absolute best single origin beans money can buy, or delicious flavored lattes, you’ll find it in Portland. 

The thing to know about Portland is that you can find great coffee on basically every other corner. Please, whatever you do, skip Starbucks and at least try a local coffee shop. 

When it comes to where to find great coffee, it really depends on what you’re looking for. Here are three places I love, and what they’re good at. 

Courier Coffee: In a city of very hip and trendy coffee shops with similar decor, I love Courier, who has been roasting coffee in Portland for more than a decade. They do things their own way, and they do them unapologetically. It reminds me of how Portland (and Seattle, which is where I grew up) was about ten years ago, before all the money started to flow in. And I mean that in the best way possible. Their coffees are great, and the owner is also an avid baker, so they have fun pastries (like the caneles!) that you should definitely try. 

Never Coffee: The highlight here is their signature lattes. I love the Midnight Oil, a delicious combination of fennel, star anise, and black licorice, which is a fun, inventive flavor combination I would never have expected. There are plenty of other options, so if that seems a little too out there for you, they have others that are a little less adventurous. Their design aesthetic is delightful, too, with color-coded mugs (depending on which latte you order) and pops of bright color throughout the shop. 

Stumptown at the Ace Hotel: In many ways, Stumptown is the OG coffee shop in Portland, and arguably kicked off the third wave coffee revolution around the world (or at the very least, hit the fast forward button). Today, they’re owned by a multinational corporation and have locations around the world, but I still love the ambiance at their location on the ground floor of the Ace Hotel. 

Signature lattes at Never Coffee in Downtown Portland
Signature lattes at Never Coffee in Downtown Portland
A perfect cappuccino at Stumptown Coffee in the Ace Hotel Portland
A perfect cappuccino at Stumptown Coffee in the Ace Hotel Portland

If you’re into coffee and wondering where to find the best coffee in Portland, we have an entire guide – written by me, a huge coffee snob – to the best coffee shops in Portland. You’ll definitely want to read that if you’re on the hunt for amazing coffee while you’re in town. 

The PSU Farmers Market

The PSU Farmers Market – which covers several city blocks on Portland State University’s campus downtown, is quite a spectacle. It is easily the best farmers market we’ve ever been to, and it has an eclectic mix of local produce, local food producers (think kombucha and fresh corn tortillas), and ready-to-eat food stands. 

There are a couple of food stands worth noting here – Enchanted Sun Burritos (for their New Mexico style breakfast burritos) and ROAM (for their delicious Roti). 

Powell’s City of Books

I love Powell’s. Full stop. You’ll often find me out and about – in Portland and beyond – in my light blue Powell’s Books shirt that I bought almost a decade ago, and every time I wear it I get at least a couple of people who come up to me and say “I love Powell’s!”

If you’re not familiar, Powell’s is the largest independent bookstore in the world. If you’re an avid reader and book lover like me (Matt), I challenge you to walk into this place and not walk out with 30 pounds of books. I’m pretty sure it’s impossible. 

You could honestly spend hours wandering the shelves here. There are many floors, all mostly organized by genre, and we still haven’t quite explored every nook and cranny here. 

I got a chuckle out of this one

I personally love the section in the entryway, which has a bunch of staff picks and sale books to peruse. Start there if you’re not sure where to begin your journey.

It’ll probably take you an hour or two to explore here. Take your time and find a book or two to take home as a souvenir. 

Washington Park: The International Rose Test Garden + Hoyt Arboretum

One thing to know about Portland is that it is a city of incredible green spaces. Forest Park, for example, is 5,200 acres of urban forest (one of the biggest urban forests in the country). 

Of the many amazing parks in Portland, Washington Park is our favorite. We find ourselves here often, mostly because the rose garden is one of Alysha’s favorite places on earth. 

There are two things we think you should focus on here if you have limited time – the International Rose Test Garden, and Hoyt Arboretum

There’s also the Portland Japanese Garden, which is definitely cool, but isn’t free to visit like the other two spots. 

With limited time, we’d focus on the Arboretum and rose garden, and save the Japanese Garden for next time. 

We’d start with a stroll through Hoyt Arboretum, then head down to the Rose Garden. That way, the journey between them is downhill, and from the rose garden, you’ll be able to walk down into the Northwest District for dinner, ice cream, and drinks to cap off your first day in Portland. 

To get to Hoyt Arboretum from downtown, the easiest thing to do is hop on the MAX line at Galleria/SW 10th Ave (here on Google Maps) and grab a westbound train on either the red or blue line to Washington Park. It costs $2.50, and you can buy tickets at the machine on the platform. 

You’ll arrive at the Washington Park MAX Station, which is the deepest subway station in the country, and the fourth deepest in the world – a fact that blows my mind every time I see it. 

From there, you can either walk up the hill to the Arboretum (here’s the route), or take the free Washington Park Shuttle that links the two (although there are usually long lines midday on a weekend). 

Hoyt Arboretum

Hoyt Arboretum is essentially one big tree nursery, holding more than 2,000 different species of trees coming from six continents. It’s a lovely place to spend an hour wandering and learning about the different ecosystems they’re cultivating here. 

It’s also completely free to visit (though parking is not free), which is another bonus.

There are several options in terms of hiking at the Arboretum, and we’d make sure whatever route you choose includes a visit to the Redwood Deck, which we enjoy. This trail is a nice, short hiking option.  

Here’s a more robust map of the hiking trails running through the park. 

In terms of getting between the arboretum and rose garden, you have a few options. 

You can link them with a quick and easy walk through the woods, you can drive between them, or you can turn it into a lovely five mile hike that explores broader Washington Park that is one of our favorite hikes in Portland

There’s also a free Washington Park shuttle that runs between them. It comes every 15-30 minutes. 

The International Rose Test Garden

The International Rose Test Garden is magical, especially in the late spring and early summer (around May and June). There are more than 10,000 roses (all cataloged and organized, which you can see on the signage in the middle of the garden). 

It’s a popular place for obvious reasons, and we actually have a recommendation for a less-visited but equally beautiful park to visit on your second day that is actually the oldest rose garden in the city. 

For a great view of Mount Hood peeking through the dense forest, head here (roughly) to the stone stairs connecting the tennis courts to the rose garden. 

An Afternoon and Evening in Portland’s Northwest District

After you’re done in Washington Park, we’d recommend walking down the hill into the Northwest District to finish off your first day in Portland with some dinner and drinks. 

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 boutiques, 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.

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 M Bar for their rotating selection of wines by the glass and by the bottle (and great happy hour deals). 

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. 

Ice Cream at Salt & Straw

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. 

At the time of writing (it’s September), they have a Spiced Goat Cheese Pumpkin Pie and a Beecher’s Flagship Cheese with Apple Pie (Beecher’s is a Seattle cheese company) that look amazing. 

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 of the River

On your second day in Portland, spend your time on the other side of the river, which is our personal favorite part of the city. 

In many ways, this is the area that makes Portland special, and put Portland on the map as a quirky, unique place to visit (hence the unofficial  slogan “Keep Portland Weird”). 

On one hand, there are some truly amazing food and drink spots to be had here (you absolutely have to eat at one food cart on your first trip to Portland), some great vintage shopping and consignment stores, and an overall lovely mix of small businesses selling all sorts of different things.

On the other hand, it’s much harder to get between places on this side of the river, which means you’re going to have to be prepared to either bike (we use – and love – the orange Biketown bikes), use a rideshare (we use Lyft), or take the bus to get between places. 

We’ll give you recommendations on how to get between each set of places below, but we’d also refer you to the “Getting Around” section for more details on how to use the bikeshare and buses in Portland. 

The other thing to know is that there are a bunch of places to eat on the eastside that are just not practical if you don’t have a car (exhibit A: Pip’s Doughnuts and Chai). We won’t include them here, because we absolutely don’t recommend renting a car for a weekend trip to Portland, but you’ll find some of them over in our guide to the best places to eat in Portland (forthcoming). 

Last, but certainly not least, we spent a decent amount of time figuring out what order to put these three neighborhoods in based on what time of day they really shine. However, we constantly found ourselves saying things like “yeah, but XXX and YYY are also great for dinner, so should we move it to the end of the day?”

Turns out, all three of these areas are excellent places to explore at all hours.

Here’s our best attempt at consolidating the entire east side of the river into one action-packed day. 

Breakfast and Coffee in the Alberta Arts District

We went back and forth as to whether this should be the first or last stop of the day, and ultimately landed with it being stop #1 on your tour-de-Portland’s-Eastside.

The reason? It has a few of the best coffee shops in Portland, AND a few of the best brunch spots in Portland. 

So, it makes sense to start your day with coffee and brunch on Alberta Street. 

For coffee, you have two excellent options on Alberta. 

Proud Mary is my absolute favorite place to get coffee in the city (read my guide to Portland’s best coffee for more!). They have single origin coffee available as drip or espresso, and some really special coffees that you would never get to try elsewhere.

They do a great job, which is unsurprising since they’re from Melbourne, Australia, the world capital of hipster coffee. 

Barista is another great option. They specialize in espresso drinks (like cappuccinos and lattes) and give you a choice between two or three different coffee beans to use in your drink.

Also, fun seasonal drinks, like an iced coffee with ube foam in the summer. They bring in roasters from around the world, so it’s a fun place to try coffees you wouldn’t ordinarily find at home. 

For brunch head to the Tin Shed Garden Cafe for a more sit down brunch experience, or to Pine State Biscuits for Portland’s famous biscuit sandwiches. Expect to wait in line for both. 

A breakfast brisket biscuit drowning in ranch

To get to Mississippi Avenue, your next stop after brunch, you have a couple of options. 

Our top recommendation is to take the 72 bus westbound to Peninsula Park, which is the oldest rose garden in Portland and is much more low key than the one you saw yesterday (we often walk here in the morning from our house – it’s gorgeous).

Here’s that route

Refer to the “Getting Around” section below for how to ride the bus (spoiler: it’s easy!). 

From the park, you just walk south on N. Albina Ave! 

You could also pick up a Biketown bike at one of the stations on Alberta and ride it to the park, then walk the same stretch of Albina. 

If you don’t feel like walking or biking, a rideshare is the next best option. 

Lunch and Shopping on Mississippi Avenue

Welcome to our neighborhood! This is a prime example of where we started to say things like “yeah, but Interurban is such a good bar, maybe it should be at the end of the day!” 

However, the highlights here, at least for us, are the food cart pod at the north end of the street, and the shopping from there to the south. 

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). 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.

Famous Matt’s BBQ, a food cart serving Texas-style barbecue in Portland

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 brunch restaurant nearby called Masala Lab, which is worth a visit on a later trip (get the amazing hash with housemade bacon). 

  • If you missed it on your first day, Fried Egg I’m in Love – which has been rated the second best breakfast sandwich in the country – has a cart at this pod too. 
The cardamom chai chicken at DesiPDX is spectacular

After lunch, walk south down Mississippi. There are tons of places to shop here, like another location of the Meadow (the salt/chocolate/bitters store from yesterday) 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. 

For more places we love, refer to our guide to Mississippi Avenue (coming soon!).

The other thing you should do here is grab a cold locally-brewed beer. There are two great options here – Stormbreaker, which has a lovely patio and live music on weekend evenings, and Ecliptic Brewing, which is a little down the hill. We can’t choose between them ourselves, so it’s up to you (or, why not both?!). 

After that, your next stop is Hawthorne and Division 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 Evening in Southeast Portland

For the afternoon and evening, explore two of our favorite stretches in the city – Hawthorne Blvd and Division Street

There’s a ton to do and see here, and it’s nearly impossible to fit it all into one afternoon and evening. We’d focus on shopping, then grab a drink, and end your day with dinner. 

As far as shopping goes, we’d start from here, and wander east along Hawthorne, which is lined with all sorts of shops and vintage stores. The best stretch is between 30th and 38th or so. 

Here are some suggestions for dinner. Some of these are on Hawthorne, some on Division, which are about five blocks away from each other. It’s a nice place to walk, so we’d just walk from Hawthorne to Division if that’s the direction you’re headed. 

For plant-based burgers, head to Next Level Burgers at Hawthorne and 41st. 

For great Mexican food (and margaritas), head to either ¿Por Qué No? (Hawthorne and 47th) OR Taquería Los Puñales (Belmont and 33rd). 

For a cool beer garden atmosphere and alpine-inspired (as in the Alps) cuisine like sausages, spaetzle, and risotto, head to the Olympia Provisions Public House.  

Definitely don’t miss Lauretta Jean’s for their homemade pies (it’s at Division and 34th)!

What to Do with More Than 2 Days in Portland

If you have more than 2 days in Portland, congratulations! The extra day is going to give you the opportunity to dive a little deeper into what makes Portland and the area around it special. 

Our top recommendation is to get out into nature, either in the form of a day trip from Portland, or an urban hike. We cannot emphasize our love of the green spaces in and around Portland enough. 

The best part? There are several great green spaces that are accessible even if you don’t have a car! 

P.S. We have an entire guide to spending 3 days in Portland, which you should go over and read if that’s the amount of time you happen to have. 

Take a Day Trip

One of our favorite things about Portland is the fact that, within 90 minutes, you can be either in the mountains or on the coast. The sheer amount of natural beauty within 90 minutes of the city is staggering. If you have an extra day or two in town, we’d highly recommend using that extra time to get outside of the city and explore that beauty!

We have an entire guide to the best day trips from Portland which has far more detail than you’ll find below. 

Here are three great day trip options. 

The Columbia River Gorge

The Columbia River Gorge is just a half hour outside the city, and is a paradise of lush forests, towering waterfalls, and great views. The Columbia River runs east to west along the northern border of Oregon, separating Oregon from adjacent Washington State. 

There are worthwhile attractions on both sides of the Gorge, but we’re going to focus on the Oregon side here, because it’s closer to the city and home to a staggering number of great waterfalls. 

In terms of getting to the Gorge, there are three options. 

First is to rent a car for the day. You could use Turo, or you could rent a car from one of the major car rental companies in town. 

Second is using the Sasquatch Shuttle, which stops at many of the main attractions on the Oregon side of the Gorge. The downside is that you’ll have to get to the pickup area yourself, which will require either driving or a somewhat pricey Lyft/Uber. This means that, depending on your situation (particularly for couples), it might actually be more cost-effective to do a guided day trip if you don’t have a car (more on that below).

Last is taking a guided tour that includes transportation from Portland. This is the most expensive option, but is the most convenient if you don’t have a car. Once you factor in the price of a car rental, it’s not that much more expensive, and it’s far less hassle. We’d recommend this half day tour or this tour that gets you to three waterfalls at the western end of the Gorge.  

If it’s your first time to the Gorge, here’s what we would do.

Start at Multnomah Falls to beat the crowds and walk up to the bridge for a great view of the falls. Then, head to Horsetail Falls, and do the one mile hike up to Ponytail Falls, which is cool because you can hike up behind the falls. Finish with a hike to Latourell Falls on your way back to the city, and make sure to drive along the Columbia River Scenic Highway and stop at the Vista House and Women’s Forum Viewpoint for some great Gorge views. 

Silver Falls State Park

Silver Falls State Park is home to the Trail of Ten Falls, which is exactly what it sounds like. In terms of the concentration of beautiful waterfalls, it’s hard to beat this 8 mile loop. Both the South Falls and North Falls are spectacular, and there are eight other falls to be had along the trail between the two. 

Silver Falls is an hour south of Portland, and there is no way to get there with public transportation. You will either have to drive yourself, or you can take a guided day trip.

If you absolutely cannot get a car (for example, if you’re only in town for a couple of days) and still want to see some waterfalls, this guided tour with transportation is a good option. 

The Oregon Coast

If you’re more interested in the coastal beauty in Oregon, a day trip to the Oregon Coast is possible. It’s a little further, at 90 minutes or so, but it’s a different landscape than the other two options above. You also need a car here – there’s really no other way to do it. 

Our recommendations in terms of what towns to visit would be Astoria, which is known for Lewis and Clark-related history and breweries, or Cannon Beach, which is better for coastal hiking and sandy beaches. 

If you go to Astoria, don’t miss Fort Stevens State Park and the Peter Iredale Shipwreck, the Astoria Column (climb to the top for great views!), and a walk along the waterfront (with a stop at either Buoy Beer or Fort George Brewing). 

If you choose Cannon Beach, the highlights for us are Ecola State Park, which has great coastal views and beaches just north of town, Short Sand Beach in Oswald West State Park, and Haystack Rock which is the towering sea stack on Cannon Beach itself (with a lively puffin colony). 

OMSI

If you have kids, OMSI (the Oregon Museum of Science and Industry) is a fun way to spend a few hours. It’s a cool museum with lots of interactive exhibits, mostly focusing on Oregon’s ecosystems and some rotating exhibits. 

They also have a cool “after dark” series that sees the museum turn 21+ and serve drinks, featuring different themes and talks and exhibits related to those themes. 

For example, we went to one focused on the ocean, and there were guest speakers about how  the sea otters are key to saving the world (from the excellent Elakha Alliance, and I’m only slightly exaggerating), a cool film about Great White Sharks in the huge theater, and various other features. 

Hike to Pittock Mansion

We really tried to find a way to work this into the itinerary above, but it just doesn’t make sense given limited time, and we’d opt for the Washington Park sights instead. 

Forest Park is the other great park near downtown Portland, sprawling for miles northwest of the city center. 

One of our favorite hikes in Portland is the hike from the Lower Macleay Trailhead up to Pittock Mansion. It passes the Witches Castle along the way, which is a graffiti-covered old park structure, and climbs up to Pittock Mansion, which has an excellent view of the city. 

We wouldn’t actually go into Pittock Mansion – it’s just kind of a well-preserved rich person’s house – but the hike up there is definitely worthwhile.

If you don’t have a car, take a rideshare to the Lower Macleay Trailhead (here on Google Maps), do the hike one way up to the mansion, and then walk downhill into the Northwest District from there (or take another rideshare). 

Catch a Portland Timbers Game

The Portland Timbers play in Major League Soccer, the highest level of professional soccer in the US, and are known for having one of the best atmospheres in the country (okay, THE best) thanks in large part to the Timbers Army, a committed group of Timbers fans. 

A lot of times, you’ll find that the stadiums for major sports teams around the world aren’t really in the center of the city, and it can take an hour or two to get there and back. Which, given a short visit, isn’t entirely feasible. 

However, Providence Park, which is where the Timbers play, is smack dab in the heart of downtown Portland. Many locals even ride their bikes to the games!

We’ve been to several games at Providence Park, and it’s a fun atmosphere whether or not you like soccer (Matt is a fanatic, Alysha couldn’t care less). 

Check the schedule here – the season runs through the summer and fall, with most games falling on weekend afternoons and evenings. 

Getting To Portland

Getting to Portland is easy if you’re flying in.

Portland International Airport (PDX) is one of the best airports in the country. That’s where you’ll want to fly into when you arrive. 

Alaska Airlines is the main domestic airline flying in and out of Portland, and has direct flights from most west coast destinations, and some of the bigger cities across the country. 

Getting from the Airport to the City Center

One of the reasons that PDX is great is that it’s so close to the city center. Unlike airports like Seattle and San Francisco, where it can take an hour to get from the airport to the city itself, it’s only going to take a half hour, at most. 

If you’ve taken our advice, you didn’t rent a car for your weekend in Portland. That means you have two options for getting from the airport to your hotel – rideshare or the MAX Line. 

Rideshare is going to be faster and more convenient, but it’s going to cost more (think $20 or so for the ride, depending on where you’re headed and the time of day). 

Using public transportation is easy, with some caveats. There is a dedicated MAX Line – which is Portland’s light rail system – that runs between downtown and the airport. It’s the red line, and it runs between PDX and Pioneer Square in the heart of downtown Portland.

It comes every 15 or 30 minutes (less frequently in off-peak hours like early morning) and will cost $2.50 a person, and take 30-40 minutes. 

The caveat here is that it’s not well-connected to other parts of the city, like the Central Eastside, Northwest District, or Southeast Portland. Depending on where you’re staying, it’s not going to be a great option because you’ll have to transfer to either a bus, another MAX line, or a rideshare. 


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