The St. Johns Bridge in Portland, Oregon.

A Weekend in Portland

Portland, Oregon, is a beautiful location for a relaxing weekend getaway. Green mountain views and a metropolitan vibe make Portland appealing to a wide variety of interests. Our weekend itinerary will make it easy to fill three days in this lovely city. 

Friday Afternoon

When you first get to Portland, you are going to want to head downtown and check out some of the city’s famed landmarks. Start your trip with something sweet at Voodoo Doughnut, known for their wide variety of tasty creations.

From there, it is only a short walk down Burnside Street to Powell’s Books. One of the largest bookstores in the world, Powell’s has a collection so extensive that they give guests maps of the building. You could spend all afternoon navigating your way to a plethora of topics.

Voodoo Doughnuts

Friday Evening

After you have loaded up on books, take a walk down SW 5th Avenue, and check out the outrageous selection of food carts that have drawn so much attention from around the world. Whatever type of food is calling to you, it can be found on this strip. As it gets darker, Portland’s nightlife emerges. The city is known for its local music scene, so try to take in a concert at one of the nearby venues. Check out Dante’s, which has the famous “Keep Portland Weird” mural painted on the back.

Tom McCall Waterfront Park

Saturday Morning

On the weekends, hundreds of vendors come together for the Portland Saturday Market. Stretching from Waterfront Park into the heart of the city, the market will give you a great feel for the diverse cultures on display. You will also be able to get your fill of artisan crafts and festival food. Be sure to hang around the park to hear local musicians display their talents on stage.

Saturday Afternoon

After you grab a bite to eat, perhaps at Mandarin House, strap on your hiking boots and head to Multnomah Falls. Just outside the city, this magnificent waterfall will remind you why so many people are drawn to the natural beauty of the Pacific Northwest.

Multnomah Falls

Saturday Evening

After your hike, grab a slice of pizza at Sizzle Pie. This vegan-friendly eatery is proud of its punk rock atmosphere, and its pizza is as delicious as it is affordable. Across the street is Living Room Theater. While it might seem weird to go to the movies on a vacation, it will be a great break from being on your feet for the last two days straight. Not to mention, Living Room is an experience like none other. As its name would suggest, this intimate setting provides comfy, reserved seating with servers who bring food to you. While they have standard theater fare, they also offer specialty items and a wide variety of local beer and wine.

Sunday Morning

Start your peaceful Sunday morning at Peninsula Park. In the warmer months, you can truly appreciate the rows of blossoming roses. Portland has many public rose gardens, but Peninsula Park was the first. Plus, it doesn’t charge an admission fee. Since it first opened in 1909, the park has been a wonderful place to take a stroll, or simply sit and reflect on the gorgeous landscaping.

Portland, Oregon sign

Sunday Afternoon

Peninsula Park is very close to Mississippi Ave, so why not head over? When walking down this strip of local shops and restaurants, visitors are able to get a real grasp on what it's like to live in Portland. There are many businesses that display the city’s “do-it-yourself” attitude, so make sure you support the local vendors by purchasing some handmade souvenirs for your friends back home. Also, if the line isn’t too long, stop by Blue Star, which many consider the best doughnut shop in the entire city.

Last Updated: May 25, 2023