The Best Ways to Explore Downtown Portland: What to Do

If you only have a day or two to explore Portland, Oregon, you may be overwhelmed by all of the possibilities. The city’s compact, walkable downtown offers easy access to great food, green spaces, cultural events, and even tax-free shopping. Many people don’t know where to start, and Starfish Vacation Rentals can help! Here is our ultimate guide to downtown Portland: what to do.

Learn more about the best attractions in Portland on our Things To Do page. It’s a great resource to help you plan your vacation in the Rose City.

Downtown Portland: What To Do

Have Brunch at Tasty n Alder

Start your day downtown like a local at Tasty n Alder, one of the most celebrated brunch destinations on Portland’s west side. This hotspot is spearheaded by James Beard award-winning chef John Gorham. The menu features small plates like pork schnitzel, pan-fried halibut sandwiches, and chocolate potato doughnuts, all best enjoyed with one of their boozy milkshakes. Brunch is available from 9 a.m. to 2 p.m.

Check Out Pioneer Courthouse Square

Often referred to as “Portland’s living room”, Pioneer Courthouse Square is a 40,000-foot public space in the center of downtown PDX. The square is named after Pioneer Courthouse, an 1875 federal building occupying the block east of the square. The block itself dates back to 1856.

Today, Pioneer Courthouse Square boasts a variety of features including outdoor chess tables, a fountain, and an amphitheater. Dozens of events are held here each year, including free shows during the spring and summer. Click here for a full list of programs.

Wander Through the Japanese Garden

When the hustle and bustle of the city starts to get to you, seek out zen-like tranquility at the Japanese Garden in Washington Park. This traditional Japanese garden occupies nine acres and is comprised of eight garden spaces, including the Sand and Stone, Tea, and Strolling Pond gardens. There’s also a pavilion that hosts several cultural festivals and art exhibitions throughout the year. No matter what you choose to explore, the Japanese Garden is a great place to relax amongst nature.

Shop at the Portland Saturday Market

The Portland Saturday Market is the largest open-air arts and crafts market in the country. If you’re in the mood for a little retail therapy, stop by and browse handmade arts, crafts, and exotic foods from the Pacific Northwest. You can even chat with local artisans and listen to live music on the main stage. The market is held in the historic Old Town Chinatown neighborhood from March through Christmas Eve.

Take a Portland Brewery Bike Tour

Have you ever wanted to burn calories while enjoying your favorite alcoholic beverage? Now you can! BrewCycle Portland is a bike tour like no other. This pedal-powered trolley takes you to the city’s most popular microbreweries, including Lucky Lab, Bridgeport, and Deschutes, for an informative beer tasting. It’s perfect for reunions, birthday celebrations, bachelor/bachelorette parties, and more!

Book Your Stay with Starfish Vacation Rentals

When it’s time to find lodging in Portland, look no further than our beautiful vacation rentals. Our properties are ideal for family getaways and weekends with friends. Book your stay in our Brooklyn Cottage for close proximity to downtown nightlife and attractions, or reserve our Luna Serena home with its charming décor and spacious deck. You can even check out 617 Brownstone, an exclusive three-level townhouse at the center of Portland’s renowned Pearl District. Book online or give us a call and start planning your vacation today!

For activities and attractions that are off the beaten path, check out our blog about Weird Portland.