A Weekend in Portland, Oregon Itinerary | Things to do, food, & more!

Last updated on December 23rd, 2025

Looking to spend a weekend in Portland, Oregon? We’re sharing a detailed Portland itinerary and guide with everything you need to know before you visit including where to stay, what to eat and drink, the best things to do in Portland, and more!

Just 3 hours from Seattle lies the quirky, fun, and delicious city of Portland. We love spending a weekend in Portland because it reminds us of a hybrid of Seattle and our hometown of Austin. Similarly to Austin, it is proud of its title of being a “weird” city, is home to tons of great restaurants and food trucks, and has an artsy culture/vibe.

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We always have a blast exploring the beautiful outdoors, checking out unique shops, eating at cheap, local eateries, and obviously drinking tons of coffee.

Heading to Portland soon? Here’s our go-to itinerary and guide with all of our favorite things to do in Portland if you only have 48 hours!

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Weekend in Portland, Oregon Itinerary Map

Weekend in Portland, Oregon 2 Day Itinerary

Saturday

Have Breakfast

Start out your weekend in Portland, Oregon with breakfast at Pine State Biscuits. Everything here looks incredible. We recommend the Reggie Deluxe! We had it and loved it.

However, if you’re looking for a fancier breakfast experience, check out our “if you have extra time” section for other options!

Experience Portland’s Coffee Culture

You can’t spend a weekend in Portland and not have coffee! Some spots you certainly should check out:

Visit the International Rose Test Garden

If your weekend in Portland is from May to October, then admire all of the beautiful roses at the International Rose Test Garden. This garden is exactly what the name implies, a place to test new rose varieties.

The garden boasts over 10,000 rose bushes of 610 different rose varieties. Spend some time wandering the garden, admiring the blooms and taking beautiful photos!

The garden is completely free to visit and is located in Washington Park which is also home to the Japanese Garden!

Make a Quick Stop at Pittock Mansion

View Portland from above at the Pittock Mansion, since it is another great quick and free stop! Well, if you plan to park here then parking will be $2 per hour, but the views and enjoying the grounds is free.

If you want to tour the mansion then you can for $16.50 per adult, but we recommend just stopping here for the views!

Visit the World’s Largest Bookstore

Explore the aisles of books at Powell’s City of Books, a Portland institution and the largest independent new and used bookstore in the world. This spot, while just a bookstore, is one of the most famous stops during your weekend in Portland! You can easily spend hours here, especially if you’re an avid reader!

It’s located right in downtown and is a must-do for your weekend in Portland, Oregon!

Eat Lunch

Afterwards, grab lunch at Nong’s Khao Man Gai, which is an awesome spot for Khao Man Gai, which is a chicken and rice dish from Thailand. It sounds and maybe even looks bland, but it’s SO good!

Take some Iconic Photos

Snap a photo in front of the Keep Portland Weird Wall and then walk down to the waterfront to see the White Stag Sign.

Try the City’s Best Doughnuts

For an afternoon snack, grab a doughnut at VooDoo Doughnuts or Blue Star Donuts (or both!)

VooDoo is an iconic Portland spot with fun toppings, while Blue Star is known for fancier gourmet doughnuts. There’s a battle over which is better, so we suggest trying both and deciding for yourself. 🙂

Explore the local neighborhoods

Spend the rest of the afternoon checking out some of Portland’s cool neighborhoods and streets, which are full of local shops, restaurants, and breweries. Some of our favorites include: Alberta Arts District (lots of fun murals!), Pearl District, Mississippi Avenue (Pistils Nursery is so cute!), Division/Clinton, Hawthorne.

Have Dinner

Dinner at Por Que No?, which is a great Mexican spot and one of our favorite places to eat during a weekend in Portland!

Get Ice Cream for Dessert

Lastly, enjoy delicious ice cream at Salt & Straw (multiple locations). This is one of the best ice cream shops we have ever been to! The flavors here rotate so there’s always something new and delicious to try. They also have vegan options which is a huge plus!

Sunday

Doughnuts and coffee for Breakfast

Start the morning with mini doughnuts and chai flights at Pip’s Original Doughnuts and Chai. We LOVE this place so much! Every flavor of doughnut or chai we have tried has been amazing. The owners care a lot about the community as well!

Explore the Columbia River Gorge

Spend the second day of your weekend in Portland by driving and exploring the Columbia River Gorge.

The Columbia River Gorge is a GORGEous area just 30 minutes from Portland with tons of waterfalls, hiking, and scenic views. In our opinion, it’s one of the best things to do in Portland!

Unfortunately in the summer of 2017, the Eagle Creek Fire tore through the area, making many beloved spots inaccessible for now. Our recommended list includes some of these spots, but we will mark them as closed and change their status once opened to the public again.

There are many other spots to explore along the Columbia River Gorge, but this list is just our go-to list if we only have part of a day. If you have more time, then we recommend stopping at some of the many other spots along the way (they are usually well marked!).

Portland Women’s Forum State Scenic Viewpoint or Crown Point Vista House (OPEN): These are super quick spots where you can just drive up, park, and soak up the views!
Latourell Falls (PARTIALLY CLOSED): 2 miles round trip, 643 ft elevation gain. The loop trail at Latourell Falls is pretty easy and quick and takes you by both Latourell falls and Upper Latourell falls! If you’re short on time, then you could just visit Latourell falls, which is close to the parking area.
Angel’s Rest Trail (OPEN): 4.5 miles round trip, 1,476 feet elevation gain. This hike is pretty steep, but you’ll be rewarded with views of the Columbia River Gorge! It does get busy, so be prepared to share the trail.
Multnomah Falls (OPEN): This is a classic Columbia River Gorge stop and a must-do! You can visit the iconic view of the falls just a quick walk from the parking lot, but you can also walk up onto the bridge and up to the top of the falls (2.6 miles round trip, 813 feet elevation gain).
Oneonta Gorge (CLOSED): 1 mile round trip, minimal elevation gain. This hike is absolutely incredible! You walk through a gorge and creek bed (yes, in the creek!) before you reach a beautiful waterfall at the end. You’ll have to climb over logs and walk through water, so we only suggest making this trek if you’re physically able and don’t mind getting wet.
Ponytail and Horsetail Falls (OPEN): 2.6 miles round trip, 610 feet elevation gain. We love this trail because it’s not too long of a hike and you get to see two waterfalls! But the best part? You can walk behind one of them (Ponytail Falls)!
Rowena Crest Viewpoint (OPEN): This quick overlook is located a bit farther from the other stops on this list, but it has views of both Washington and Oregon, the Columbia River, and a super cool horseshoe curve in the road (pictured above!)

Want to get 30% off an AllTrails Plus membership? Use our code aplusk30 (you must redeem this code on the website, not the app)!

We use AllTrails Plus on every single hike and it is the most helpful hiking tool out there! Some of the features we love are offline maps (so we can navigate even without cell service), wrong-turn alerts, and its 3D maps feature, so we can get a feel for trails before we hike.

Grab a Treat on the Way back to Portland

Afterwards, grab a sweet treat on your way back to Portland at Sugarpine Drive-In, an awesome little spot with sandwiches, salads, and soft serve sundaes.

Have Dinner at a Local Portland Spot

Finally, head back to Portland. For dinner, check out Güero or Teote. Both are fast-casual spots with equally delicious food!

Get After Dinner Drinks

End your weekend in Portland with drinks after dinner. Head to Hale Pele or Multnomah Whiskey Library, which is a beautiful bar in downtown Portland.

For Multnomah Whiskey Library, walk ins are welcome, but it is a very popular spot, so expect a wait. While reservations are only technically available for members, they do have a Hall Pass where for $25/person, you can get a reservation without being a member.

If you have extra time…

Have more than a weekend in Portland? Here are some other suggestions of equally awesome things to check out!

Food

Lardo
Gumba
Pine Street Market
Ox
Mother’s Bistro & Bar
Matt’s BBQ
Pambiche
Eem
Screen Door
Cheese & Crack Snack Shop
Proud Mary Coffee (coffee + breakfast!)

Coffee

Sweets

Wailua Shave Ice: Our favorite shave ice from Kauai that also has a spot in Portland. SO good!
The Pie Spot
Eb & Bean
Fifty Licks
The Cookie Dough Cafe
Miss Oz Ice Cream & Desserts
Churros Locos
1927 S’Mores Company
East Wind Drive-In: By the Columbia River Gorge. Have one of their massive ice cream cones!

Breweries

Activities

Our top pick: Drive to the Oregon Coast and then visit Cannon Beach (1.5 hours each way from Portland). Check out our Weekend on the Oregon Coast guide for ideas!
Check out the Rowena Crest Viewpoint
Visit the town of Hood River
Visit the beautiful Portland Japanese Garden
Do the 4T Trail, since it is a unique way to explore Portland by trail, tram, train, and trolley!
Hike to Tamanawas Falls–3.3 miles, 597 ft elevation gain (~1.5 hours each way from Portland)
Visit Trillium Lake for an especially beautiful view of Mount Hood (~1.5 hours each way from Portland)
Chase waterfalls at Silver Falls State Park (~1.5 hours each way from Portland)

When to visit Portland for a weekend

While the temperatures are bearable year round in Portland and snow isn’t a huge issue in the city, Portland, similar to the rest of the Pacific Northwest, can be a bit rainy during certain times of the year.

If you want lots of sunshine, the best time to visit Portland is between June-September (May and October can also be great, but sometimes more of a gamble). The temperatures are perfect, the sun is out, and there is way less rain. The snow in the mountains is also melting, which means that more hikes are accessible.

However, if you don’t mind getting a tiny bit wet, we have visited Portland during rainier months and have always had a blast! There is still so much to do when it rains, like chase waterfalls, eat more food, drink more coffee, and wander around shops. You could even go visit a ski resort! The rainier months will definitely be less busy and cheaper, so if you don’t mind some gloom, the late fall, winter, and spring may be a great time for you to visit!

Getting to a weekend in Portland

Portland is home to Portland International Airport (PDX), which is one of our favorite airports in the US! It has tons of local eateries inside, which obviously we love, plus some ugly carpet that has become a popular thing to photograph on Instagram. If you need to fly to Portland then you should have no problem getting a flight to this major airport.

PDX is located about 13 minutes Northwest of the city, so it is about a 20 minute drive or 55 minute MAX ride to downtown Portland.

Getting Around Portland for the weekend

Portland has a great public transportation system, like the MAX light rail! Between that, walking, and Uber/Lyft, you can easily get around the city for a weekend in Portland. However, if you want to explore the Columbia River Gorge (on this guide) or any nature spots outside of the city, we highly recommend renting a car for a portion of your trip!

Where to stay for a weekend in Portland

Vacation Rentals

Similar to our other guides, we highly recommend staying at a VRBO while in Portland. There are indeed many neighborhoods in Portland and here are some options of where you could stay:

Alberta Street Option 1 (1 bedroom, 1 bathroom): A rental unit in a cute craftsman-style home that sleeps 4 and is located in a great neighborhood!
Alberta Street Option 2 (1 bedroom, 1 bathroom): This cozy urban cabin is perfect for two people complete with a full kitchen, local coffee and has hundreds of 5 star reviews.
Mississip p i Ave (1 bedroom, 1 bathroom): This modern Micro-loft (aka tiny home) is upgraded and has everything you could need in this small but still comfortable space!
Woodlawn Option 1 (1 bedroom, 1 bathroom): An adorable greenhouse turned VRBO that’s super modern and cute.
Woodlawn Option 2 (2 bedroom, 2 bathroom): A stunning Victorian home with a private hot tub!

Hotels

If you would rather stay at a hotel, here are some good options:

Looking for more things to do in Oregon? Check out these guides & videos:

Ready to get enjoy a weekend in Portland?

Pin this weekend in Portland guide to help plan your trip!