How to Plan the Ultimate 3 Day Weekend in Portland, Oregon

3 Days In Portland Downtown
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While I enjoy spending time in Washington state, it’s always a treat to go down to Oregon to spend a weekend in Portland. It’s a fun city to get out in, and I love exploring new breweries and food carts while I’m there. I’ve been there for bachelorette parties, conferences, and just because countless times.

I’ve explored many places in Oregon over the years, including the beautiful city of Astoria by the Columbia River and the excellent wineries of Willamette Valley. While I always recommend people visit different parts of a state, I always tell people to visit Portland. Many tourists stop by Portland for lunch on their way to another city, but I recommend spending a full 3 days in Portland to really experience the area.

From how to get to Portland to the best things to do to a sample Portland weekend itinerary, this guide includes everything you need to explore The City of Roses.

How to Get to Portland

Regardless of where you’re traveling from and what mode of transport you’re looking to use, reaching Portland is easy. You can make your way to the city via plane, by train, or by driving yourself there.

If the trip starts in one of the cities near Portland, using your car is a good option. There are many routes to choose from, including interstate 5 and interstate 84. If Portland is a stop as part of a long road trip, consider this Pacific Northwest road trip itinerary to add some fun to your drive.

An airplane is best for travelers making a Portland trip from outside the United States. The city is home to the Portland International Airport (PDX), considered one of the nation’s best airports for years. There are flights to the airport from nearly every country in the world.

For a budget-friendly alternative to driving, consider hopping on a train for a unique experience. Amtrak’s three routes are a popular choice for traveling to Portland from major cities such as Minneapolis, Seattle, Los Angeles, and Chicago.

How to Get Around Portland

Trimet Max Light Rail

Similar to making your way to Portland, getting around the city is easy during your Portland weekend trip. The city is full of fantastic transport systems, whether they’re public or private. The sheer number of options available means you may not even need to rent a car.

You can get around at all hours of the day using popular services like Lyft and Uber. Their drivers are readily available to chauffeur you around from place to place.

If you’re budget conscious, you’ll be happy to know Portland has a great (and cheap) public transportation system. The whole thing is run by Trimet, which offers buses, streetcars, and light rails at incredible prices.

Portland is full of biking lanes, so if you don’t mind working up a little sweat, you can choose a bike as your mode of transport. You can rent a bike at one of many bike shops, or you may get one for free from your hotel.

When to Visit Portland

Portland weather, much like anywhere in the world, varies from season to season. Therefore, there isn’t really a bad time to visit Portland. However, there is a great time to visit the Pacific Northwest – during summertime. 

Summer (July to September) has dry, moderate, and sunny days and cool nights, perfect for partaking in many of the best things to do in Portland, Oregon. It rarely rains, and temperatures usually sit around 80° F. Unfortunately, it’s the city’s busiest period, where attractions and experiences are pricier and more crowded due to the influx of visitors.

During spring (April to June), Portland weather is a little less predictable. However, temperatures are usually cool, clouds are grey, and there are occasional showers.

Fall (October to mid-November) is filled with cool temperatures that border on cold. It also rains more frequently than in summer and spring.

Winter (December to March) typically features cold days and nights with gray clouds, and it’s Portland’s rainiest season. It’s a perfect visit for cozy days spent in cafes and restaurant hopping. To ensure you don’t get wet during your weekend in Portland, Oregon, I recommend getting a rain jacket.

Where to Stay in Portland

Weekend In Portland Sign

Where you decide to stay during your visit depends largely on your needs and what you want to do in Portland. You can decide to stay in lively downtown or the more quiet and residential areas of the city’s eastern part.

No matter the size of your budget, there’s a place to stay for everyone. Whether you want to splurge on a deluxe hotel or get a homey feel at a VRBO rental – you’ll find it. 

Since you’re spending a weekend in Portland, being rooted in one neighborhood may not be the best way to go. That’s why I’ve recommended the following city areas and their respective hotels or home rentals.

Downtown Portland

Downtown Portland

Downtown is where you’ll find most of Portland’s visitor attractions, and it’s also the busiest part of the city. It’s an ideal area to stay in because there are so many things to do in Portland here. These are the places I’d recommend staying at in the area:

The Hoxton is easily one of the best places to stay in Portland. This fun hotel has well-decorated rooms featuring floor-to-ceiling windows and free Wi-Fi, as well as in-house restaurants and bars. It’s also conveniently located close to many shopping, food, and drinks spots.

The Ace Hotel caters to all travelers with cozy rooms for most budgets. It offers free Wi-Fi, a flat-screen TV, as well as stocked minibars in each room. Delight your palates at the hotel’s restaurant and cafe.

This amazing pet-friendly condo downtown is excellent if you’re looking for a more secluded stay  Downtown. It features Wi-Fi, a chic interior, a TV with Netflix, and more amenities, plus it spoils you with panoramic views of the city. I recommend it because of its proximity to restaurants, bars, and other attractions in the area.

The Pearl District

Portland Overhead Shot

The Pearl District is the “pearl” of Portland for anyone searching for a trendy area as it features excellent restaurants, art galleries, and more. I recommend staying in the following places in the Pearl District.

The Society Hotel is an affordable accommodation that features incredible decor in the rooms and an on-site bar, cafe, and restaurant. The rooms offer free Wi-Fi and stunning views of the city, which you can also enjoy from the rooftop terrace. It’s close to many nightclubs and bars, perfect for nightlife lovers.

This pet-friendly waterfront condo is in a quiet and central location in the Pearl District. It has a pool and hot tub, plus the room offers a view of the river. It’s within a short distance to many attractions in the area.

Southeast Portland

This area is the quieter yet more lively side of Portland. Staying in this neighborhood is perfect for intimate getaways. 

Jupiter NEXT is an incredible hotel that offers modern accommodations close to several city attractions. It has an on-site restaurant and bar, and the spacious rooms feature a flat-screen TV with cable and free Wi-Fi. Enjoy amazing views of the city from your room or the patio.

This two-bedroom apartment in the neighborhood is light and airy and features great amenities such as a coffee maker to kickstart your day, Wi-Fi, and a washer/dryer. Enjoy great views from the patio, or end your day glued to cable TV.

Northeast Portland

Northeast Portland is home to a vibrant and diverse group of communities. It’s arguably the best area for nightlife and live music. I recommend staying at the following places:

McMenamins Kennedy School was once an elementary school, but today it stands as unique accommodation. The rooms are cozy (especially during winter in Portland) and come with free Wi-Fi as well as a private bathroom. Soak in the heated saltwater pool to end your day in a perfect way (and make sure to check out their amazing selection of beer).

Country Inn & Suites by Radisson is located only a few minutes away from the PDX, making this a perfect place to stay upon arrival in Portland. This inn features rooms with a  TV that has cable, a coffee-making area, and other essentials. Enjoy a complimentary breakfast in the morning, then end your day by jumping into the heated indoor pool.

This pet-friendly apartment in Concordia is nestled on a quiet street close to many amazing diners and restaurants. The cozy accommodation features Wi-Fi, a washer and dryer, a smart TV with Netflix and Amazon Prime, and more. Being located just a short distance from the PDX, it’s also a great place to stay.

Where to Eat and Drink in Portland

Burger Getting Grilled

Everyone can agree that one of the best parts about traveling is tasting local cuisine you won’t find where you come from. Eating and drinking (tequilas and coffees alike) is also just an essential need to keep energized during your 3 days in Portland. 

To ensure you get to eat top-tier local food in the city, I’ve compiled this list of recommended eateries, cafes, and bars. Since you’ll have the entire weekend in Portland, you can try them all (well, most of them).

Where to Eat in Portland

While I love telling people what famous food in Seattle to eat, Portland also has a great reputation for its food. Whether it’s cheap fast food or seafood from an upscale restaurant, several places to eat cater to different individuals and their budgets. These are a few that I’d recommend.

Diners & Restaurants

In northeast Portland sits Bollywood Theater, an incredible casual stop Indian diner. The place serves authentic Indian cuisine, including street food and traditional curries. All while old Bollywood flicks play in the background.

You’ll find Mother’s Bistro & Bar near downtown Portland, a chic homey cafe and bar specializing in classics. These include fried chicken, turkey Reuben, lox platter, and more. Plus, you can down the food with drinks such as Bloody Marys and so on.

In northwest Portland, you’ll find Paley’s Place Bistro and Bar, an upscale spot selling various dishes in a Victorian setting.

In southeast Portland, I recommend a visit to Gino’s, which sells locally sourced Italian-inspired cuisines and seafood, alongside an extensive wine list.

I’d also recommend visiting Teote House Cafe for Latin American food, Taqueria Los Puñales for Mexican cuisine, and Tusk for Middle Eastern delicacies.

Donuts & Ice Cream

Portland Donuts

Portland is famous for its donuts and ice cream spots, which always brings up the debate on the best. Luckily, you can get to this conclusion all by yourself by visiting these places and trying them out. The most famous donut shops are Voodoo Doughnuts and Blue Star, but below are a few lesser-known ones to stop at during your weekend trip to Portland.

Pip’s Original Doughnuts is found in Northeast Portland and has many great options served alongside great coffee and chai.

Sesame Donuts, found in downtown Portland, is another great contender for the best donut shop. They have several selections on offer, including seasonal ones like Valentine’s Day donuts. You can indulge in them as well as coffee, tea, espressos, or sandwiches.

For ice cream, I’d recommend Salt & Straw near the Pearl District, which offers various flavors, including some that are gluten-free. Kate’s Ice Cream in northeast Portland opens on weekends only, and they sell plant-based and gluten-free ice creams in several flavors.

Carts on Foster

If you’re a fan of indulging in cuisine from different cultures and countries, you must include these delights from Carts on Foster. It’s an assortment of 17 different carts that sell diverse, authentic food, including Turkish delights, American foods, Italian cuisine, and more. Plus, it has an art gallery and a beer garden to add to your Portland itinerary for 3 days.

Where to Drink in Portland

Similar to the plethora of Seattle breweries, Portland has a great drinking scene to match its food reputation. There are several spots selling coffee and tea, cocktails, beer, and more.

Coffee & Tea

Steaming Hot Tea

Coava is a prime spot for coffee and has four different locations around Portland, plus you can buy some beans to take back home with you after your weekend in Portland. Smith Tea in east Portland sells various tea drinks they’ve been making since the 1940s, so you can’t go wrong here. 

Other great options here in Tao of Tea, Heart Roasters, and Stumptown Coffee Roasters.

Beer & Brews

Beer And Cloth

For people who love to wet their whistle with beer, there are several options. I’d recommend visiting the southeast side Cascade Brewing which offers handcrafted sour beers on a street-facing patio. Around Northeast Portland, you’ll find Upright, a microbrewery featuring handcrafted draft & bottled beers with snacks on the side.

On the northwest side of Portland, the award-winning Breakside Brewery is worth putting on your Portland 3 day itinerary thanks to its craft beers that you can enjoy on a rooftop patio with American delights. Sandwiched between the Pearl District Downtown, Deschutes Brewery features beers brewed on-site and pub grub for your pleasure.

Ciders, Wines, & Everything in Between

If beer isn’t your thing, don’t fret, as other options can give you a buzz during a weekend in Portland.

For ciders, I recommend the award-winning Cider Bite in the Pearl District, which has 32 hard ciders on tap plus plates and snacks. If you love tasting wines paired with different food, you’ll adore Noble Rot on the east side of Portland. Their selection includes wines from France, Italy, Spain, New Zealand, the US, and more.

If all you want are cocktails, then a visit to east Portland’s Vintage Cocktail Lounge is recommended. They sell various cocktails as well as other drinks like gin, whiskey, vodka, and more. Plus, they have hotdogs which you can down with your beverages.

A 3 Day Weekend in Portland Itinerary

Now that you know where you’ll stay, drink, eat and when and how to visit Portland, it’s time to get to the nitty-gritty stuff – how best to spend a 3 day weekend in Portland. For the purposes of the itinerary, I’m assuming you’re visiting during summer; however, most things here are available all year round.

To best maximize your 3 days in Portland, Oregon, I recommend participating in the following activities. Whether your idea of fun is a buzzing nightlife or an intimate and quiet adventure, you’re sure to find it below when looking for what to do in Portland this weekend.

Day 1

Portland In Fall

I’m starting this Portland, Oregon itinerary in Downtown and its surrounding areas (Pearl District and Nob Hill) because it’s arguably the best place to stay. Your first day may look different if you stay elsewhere, but it still applies since the Trimet transport system is at your service.

You’ll start the first day of your weekend in Portland at one of Downtown’s many cafes by grabbing a coffee, tea, espresso, and a small breakfast. Get your breakfast fix from the ones I listed above, or Pájaro and Café Ponté.

Afterward, I’d recommend making your way to the Portland Art Museum to view the splendid work of various artists. The museum showcases Asian, American, and Native American pieces in the form of paintings, sculptures, and more. Plus, it plays host to touring shows and theaters when looking for things to do in Portland this weekend.

Depending on what time your day may begin, you may have a late-morning sugary snack at Sesame Donuts or opt for lunch at the contemporary Southpark Seafood

After you’ve filled up your belly, go up north to continue the journey and land at Powell’s City of Books, Portland’s premier bookstore and landmark. The place is huge, so much so you get a free store map. 

It’s packed to the brim with books, both old and new; you’re likely to find that elusive book you’ve been looking to purchase. You can rip through a few pages while enjoying the coffee from their in-store cafe when visiting Portland in a weekend.

Portland Japanese Garden

Next, you can either go east to the Lan Su Chinese Garden or west to the Portland Japanese Garden to embrace the flora – you’re in the City of Roses, after all! I’d recommend going to the latter during your three days in Portland, so you also get to visit the International Rose Tea Garden, which is dotted with over ten thousand plants.

Plus, the area is close to the Pittock Mansion, a 1914 mansion-turned-museum, an iconic Portland landmark you have to visit. There’s a music room boasting a piano and a harp. 

A few minutes away is the abandoned house Witch’s Castle – visit it if you want some Instagram photo opportunities. It starts at the Lower Macleay Trailhead, and you’ll make your way up the woods until you reach the spooky place.

It should be late afternoon at this point, and you’ll have to make your way back to the lively Pearl District to continue the fun. Stop by Khao Soy or Thai Bloom! to fill your stomach. 

After that, go around exploring the area’s boutique shopping spots like Mercantile Portland, MUJI Portland, and Sloan Boutique. After all, Portland doesn’t have a sales tax.

End your day with either dinner from Swagat Indian Cuisine, Yama Sushi & Sake Bar, or upscale Portland City Grill. I’d also recommend the Xport Rooftop Lounge, which sells international food and various cocktails, all while offering scenic views of the Portland skyline.

You can also end it with a night full of booze at Shake Bar or Mingle Lounge before retiring to your hotel.

Day 2

Portland With Sunset

I’m assuming that day 2 of your Portland in 3 days journey is a Saturday, and you’re waking up in or around Downtown. If that’s the case, a quick visit to the Portland Farmers Market or Portland Saturday Market is on the cards.

The former is a haven for fresh produce, and the latter offers craft & gift vendors, food carts, entertainment, and more. Make sure you visit a cafe or eatery to grab breakfast and tea or coffee during your weekend in Portland.

For day 2, I recommend the northeast Portland area. Make your way there over the iconic Broadway Bridge and try to get a beautiful photo if you can. Since it will be right between breakfast and lunch, you can enjoy brunch at Kimura Toast Bar or Little Griddle before you get into your journey.

Make your way to The Wishing Tree, an iconic landmark where you can read other people’s hopeful messages or leave your own. Also, visit PDX Red Wall to snap an icon picture to serve as a memory of your time in Portland.

Distant Portland Photo

Another great spot to visit, especially when with a romantic partner, is Peninsula Park. It has lush greenery and incredible flora, perfect for picnics or just gazing at the sky. You can also visit the Paul Bunyan Statue for a picture next to a 30-foot-tall landmark.

For lunch, I recommend dining at Matt’s BBQ for various beef dishes, XLB for Chinese cuisine, or visiting one of the food trucks and carts scattered around the area. You can find many of them as part of this Portland food carts bike tour.

Whether you’re an artsy person or not, your first venture into northeast Portland should be the glorious Alberta Street. It’s dotted with art galleries showcasing pieces from all over the world, including Guardino Gallery, Talon Gallery, Alberta Street Gallery, and more. The street also has boutique shops where you’ll be happy to spend your money.

City Of Portland

If you love to embrace Mother Nature, there are two places I’d recommend around Roseway. The first is the Catholic church-owned “The Grotto,” a sanctuary that boasts beautiful flora. The other is the Rocky Butte Natural Area, perfect for relaxing around greenery while enjoying dramatic views of the city, airport, and the river.

If you have kids joining in on the trip, or you’re a kid at heart, I recommend a visit to Rainier Amusements for a fun experience. It features games, rides, and an assortment of attractions for all ages.

Since southeast Portland has little to offer in terms of attractions compared to other parts, I recommend heading down there to end the day. Enjoy dinner at the Italian Ava Gene’s, Coquine for American cuisine, or Tusk for Middle Eastern faves. 

You can also party the night away during your weekend in Portland at Holocene or Trio Club further up north before retiring back to your hotel.

Day 3

Portland City And Bridge

Having covered northeast and downtown Portland during your first two days, you’ve seen much of the lively parts of the city. Still, there’s more to see and explore that you should consider when planning a trip to Portland. 

You will concentrate your day around the Northwest District and the greater northwest Portland area.

Start your day with drinks and breakfast at Anna Bananas or Stepping Stone Cafe which serves huge pancakes. I recommend wearing clothing appropriate for hiking, like these shoes, as the day will be nature-filed. Also, pack food and water as there aren’t many eateries and retail shops in the area.

Before that, visit the Freakybuttrue Peculiarium and Museum which features creepy exhibits. I definitely wouldn’t recommend bringing easily-scared kids to this. The small museum is full of supernatural things you can interact with, like a bedroom with a ghost and a death-simulating coffin you can jump into.

The hiking adventure happens at Forest Park, a 5,200-acre urban forest boasting lush greenery. It features miles and miles of trails popular with runners, cyclists, and hikers. It’s home to an array of fauna, including over 100 birds and 50 mammals.

If you’re a bird enthusiast, I recommend setting up a picnic on the lawns and birdwatch Vaux Swifts as they migrate in thousands. It’s a perfect place to reconnect with nature and enjoy a serene experience.

Witchs Castle Portland

If you decided to skip visiting Witch’s Castle on day two due to time constraints, you get an opportunity to do that again here. Just start at the Lower Macleay Park trail and make your way up to Forest Park. After this, go back to your hotel to freshen up before you end the day.

After that, it should be the afternoon, and you should be right about ready to wrap your Portland visit up. Visit Papa Haydn for pastries and sandwiches or Serratto Restaurant Bar for Mediterranean food. 

I’d suggest visiting Cinema 21 and catching a flick as well; it’s a vintage theater showing classic and modern films. Plus, you can get grub and beverages from there as well.

If you’re leaving Portland by car, check out this day trip from Portland guide. It can help add to your adventure if your drive back passes by some of the places I recommended.

You can also extend your trip by heading down to a national park and finding all the fun things to do at Crater Lake National Park or going out on a road trip to the Oregon Coast.

Hopefully, this guide answered most of your questions about how to spend a weekend in Portland! Now all you have to do is enjoy your trip.

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