While Portland may be Oregon’s biggest city both in population and square mileage, Downtown Portland is a compact urban nucleus of narrow streets and high-rise buildings separated from the rest of the city by the Willamette River.
The one square mile which makes up the Downtown district is home to less than two percent of the city’s residents, but that doesn’t mean there’s a shortage of things to do there. DT Portland has everything you could possibly imagine to keep you entertained. From comedy clubs to Chinese Gardens to art, history and maritime museums plus plenty of bars, restaurants, and a fantastic, weekly handicraft market.
Tip: Explore Portland on this 2-hour walking tour.
Downtown Portland is one of the best social and cultural hubs in the entire state of Oregon. Don’t miss any of these fifteen best things to do in Downtown Portland while you’re there. You’ll enjoy all of them.
1. Downtown Portland By Segway
Get kitted out with a helmet, do a few practice laps with your Segway and then set off on a tour of Downtown.
Take in all the famous sights at a sedate speed before whizzing along the waterfront trail for a breath of river air. The guides will narrate historical information if you want them to. If not, they’ll just act as your personal navigation system, so you don’t lose your way.
The Segway tours last about two hours and are a mega-fun way of exploring Downtown Portland no matter what your age.
Book online: Downtown Portland Segway Tour
2. Lan Su Chinese Garden
Located in what was historically Downtown Portland’s Chinatown, the Lan Su Chinese Garden is a stunning oasis of Asian horticultural beauty and tranquillity right in the center of the city.
The walled botanical gardens cover around forty-thousand square acres, a full block, on DT’s Everett Street and are decorated not just with amazing flowers but pagodas, ponds full of floating lilies and koi fish and ornately decorated Chinese bridges.
Take tea in the tea house while listening to poetry or Chinese music, join a Tai Chi class or watch a demonstration of Chinese calligraphy. Visiting the Lan Su Chinese Gardens is a soul-calming experience.
3. Portland Saturday Market
Market day is Saturday in Downtown Portland and so is Sunday too. While it’s called Portland Saturday market, it’s open both days of the weekend from March right through to the end of December.
The weekly open-air market is held in Downtown Portland’s Waterfront Park and is more focused on art and handicrafts than it is on food produce. Listen to live music from various local artists while browsing the three hundred stalls stacked with handmade treasures.
There are amazing and unique gifts or souvenirs on sale ranging from original pieces of jewelry, corkscrews adorned with figures of dancing cats and handcrafted stained glass. The list is endless, and there are great pop-up food stalls to grab a tasty bite to eat from. It’s the perfect place to visit at the weekend in Downtown Portland.
4. Portland Electric Boat
Pick up an ecological electric boat at Downtown Portland’s Riverplace Marina on SW Montgomery Street and set sail to explore the Willamette River. The boats sail at a maximum of five miles per hour and are super easy to handle.
Yes, you get to captain the boat, play your choice of music through the boat’s sound system, take your own picnic and drinks or you can pre-order from the boat company’s affiliated caterer.
Each Portland Electric Boat holds up to ten people and the minimum rental period is for two hours. Nothing beats messing about on the river.
5. Portland Art Museum
The Portland Art Museum is in Downtown Portland on SW Park Avenue. The museum, which also incorporates the Northwest Film Center, has over one thousand square feet of exhibition space displaying forty-thousand individual works.
Established in the late nineteenth century, the PAM has accumulated collections which include fascinating pieces by famous masters Van Gogh, Monet and Renoir. There are also extensive collections of American, European, African plus many more contemporary artworks.
6. Harvey’s Comedy Club
Tucked away on Downtown Portland’s 6th Avenue is an intimate venue hosting top comedic talent. Harvey’s Comedy Club opened in 1992 and has been putting smiles on peoples faces ever since.
Serving food and drink as well as non-stop jokes, this is a great place to have dinner followed by the stand-up comedian of the night. Soup, sandwich or prime rib steak followed by a slice of New York-style cheesecake in a cabaret theater-style setting all makes for a fantastic night out in Downtown Portland.
Think you’re funnier than the guys on stage? Harvey’s Comedy Club holds an open-mic night every Sunday. Get up if you dare.
7. Pioneer Place
One of the in places to head for a spot of retail therapy in Downtown Portland is Pioneer Place on 5th Avenue. The mall is comprised of four entire blocks interconnected by skywalks and has a stunning glass atrium at its center.
There are over fifty stores to browse stocking a wide variety of merchandise including fashion wear, shoes, electronics, and watches. There are restaurants, snack bars and cafeterias on every level and even a movie theater showing all the latest film releases.
8. Oregon Maritime Museum
The Oregon Maritime Museum is a floating nautical exhibition in the form of a sternwheel tugboat, the Portland, docked on the Willamette River near to Downtown’s Waterfront Park.
Built in the late 1940’s, the tugboat is the last of its kind fabricated in the United States and the only one remaining in working conditions. Now almost fully restored, the boat houses maritime memorabilia. The pilothouse and engine rooms are also viewable.
The Portland makes four iconic sailings a year along the river with food and drinks included. Places are limited and so book well in advance if you want to sail on the US’s last tugboat.
9. Shanghai Tunnels
Most cities in the states have some sort of shady history, and Downtown Portland is no different. Discover the dirty deeds and deprivation of DT’s seedy past by going underground into the Shanghai Tunnels.
Meet a guide on Downtown Portland’s 2nd Avenue and enter into the labyrinth of tunnels under the streets. The creepy tales of kidnapping, the movement of illicit booze during prohibition and all sorts of other eye-opening historical facts will give you goosebumps.
The tours generally last for around two hours and cover a distance of about a mile. If you suffer from claustrophobia, this tour is not for you.
Recommended tour: Underground Portland 2-Hour Walking Tour
10. Roseland Theater
The Roseland Theater is Downtown Portland’s exciting concert venue. Located on 6th Avenue, it’s the place to go to see some of the music world’s biggest successes.
The theater has standing room for around one-thousand four hundred and just a few balcony seats issued on a first come first served basis. Expect shows which vary from chart-topping stars of the current day to bluegrass country bands to famous DJs.
The Roseland Theater also has a show and dinner venue, Peter’s Room, on the ground floor for smaller, more intimate performances.
11. Jake’s Famous Crawfish
When a restaurant has been open and serving food to a community for over a century, then you know it’s going to be good. Jake’s Famous Crawfish on 12th Avenue in Downtown Portland has been doing just that and is one of the top seafood restaurants in the entire US.
The menu varies daily depending what fish or seafood is in season, but they still offer a staggering amount of choices. If a full meal is too much, stop off there for happy hour and indulge in some of their award-winning happy hour bar food. Tasty doesn’t even begin to describe it.
12. Pioneer Courthouse Square
Pioneer Courthouse Square is a forty-thousand square foot plaza in the heart of Downtown Portland. Affectionately known as Portland’s living room, the square is where the city’s population converge to enjoy some outdoor recreation or one of the over three hundred events held there during the year.
The square is decorated with many unusual sculptures and pieces of public artwork, has a stunning cascade fountain and a fun milepost sign showing the distances from DT Portland to places all over the world.
Stay awhile, grab a sandwich from one of the food trucks and you’ll start to feel such a part of Downtown Portland, you may even want to get a floor brick with your name on it placed in the square along with the eighty thousand others.
13. The Portland Wine Bar
Savor the true taste of Oregon at the Portland Wine Bar on SW Yamhill Street in Downtown Portland. The bar showcases wines made in small vineyards, of twenty acres or less, in Oregon and throughout the Pacific Northwest.
Don’t expect to see the same wine on the menu for long. They’re small batches only from single vineyards, no blends and are rotated frequently. Once they’re gone it’s a case of waiting until the next harvest for some more to be produced.
The Portland Wine Bar doesn’t serve food but has a very nice selection of sides to accentuate the flavors of the wine. Don’t miss the truffle popcorn with grated pecorino cheese. It’s mind-blowing.
Related tour: Portland: Full-Day City & Oregon Wine Tasting Tour
14. Waterfront Park Trail
A scenic and serene way to see Downtown Portland is by walking the length of the Waterfront Park Trail. It’s also one of the best places from where to get great views of DT Portland’s bridge architecture.
Join the one and a half mile trail at Downtown’s Steel Bridge which is just one of ten in the downtown district, and amble your way along the riverside on the paved pathway. Take time for a stroll around the Japanese American Historical Plaza which is full of poems and dedications to Japanese migrants.
Continue along the trail, and it’ll take you under Burnside Bridge, past the market, and you’ll arrive at Salmon Street Springs an interactive fountain perfect for cooling off in after a long walk.
15. Mother’s Bistro and Bar
For a home from home eating experience, dine out at Mother’s Bistro and Bar on Stark Street in Downtown Portland.
Tables are set in a cozy and homely atmosphere of chandeliers, flocked wallpaper and floor to ceiling curtains. Feast on home inspired dishes like chicken and dumplings or slow-cooked pot roast until you’re too full to move.
You’ll feel so at home at Mother’s, and in Downtown Portland too, you’ll probably start planning a second visit before you’ve finished your first.