Top 15 Must-See Attractions in Downtown Portland

While Portland stands as Oregon’s largest city, both in terms of population and geographic size, Downtown Portland serves as a concentrated urban core characterized by narrow streets and towering buildings, divided from the remainder of the city by the Willamette River.

Spanning a mere one square mile, the Downtown district accommodates less than two percent of the city’s residents. However, this does not imply a lack of activities. Downtown Portland offers a diverse array of options for entertainment, including comedy clubs, Chinese Gardens, art galleries, historical and maritime museums, along with numerous bars, restaurants, and a vibrant weekly handicraft market.

Tip: Discover Portland on this 2-hour walking tour.

Downtown Portland represents one of Oregon’s premier social and cultural hubs. Ensure to experience these fifteen exceptional activities while visiting Downtown Portland; each promises to provide enjoyment and engagement.

1. Downtown Portland By Segway

Begin your experience by donning a helmet, engage in a few practice laps with your Segway, and then commence your exploration of Downtown.

Absorb all the iconic sights at a leisurely pace before gliding along the waterfront pathway to enjoy a refreshing breeze from the river. Guides will provide historical narration, should you wish for it. Otherwise, they function as your personal navigation aides, ensuring that you remain oriented.

The Segway tours usually span approximately two hours and are an enjoyable way to discover Downtown Portland, regardless of age.

2. Lan Su Chinese Garden

Situated in what once was Downtown Portland’s Chinatown, the Lan Su Chinese Garden provides a breathtaking refuge of Asian horticulture and tranquility amid the urban landscape.

The walled botanical sanctuary encompasses approximately forty-thousand square feet, occupying an entire block on Everett Street, adorned not only with exquisite flora but also pagodas, lily-filled ponds, koi fish, and elaborately crafted Chinese bridges.

Enjoy tea in the tea house while listening to poetry or Chinese melodies, participate in a Tai Chi session, or observe a demonstration of Chinese calligraphy. A visit to the Lan Su Chinese Gardens offers a restorative experience for the soul.

3. Portland Saturday Market

Market day occurs on Saturday in Downtown Portland, extending to Sunday as well. While it is designated as the Portland Saturday Market, it operates on both weekend days from March through December.

The bi-weekly open-air market is hosted at Portland’s Waterfront Park and is primarily dedicated to art and handicrafts, rather than food products. Patrons can enjoy live performances from various local artists while exploring over three hundred stalls brimming with unique artisanal creations.

From one-of-a-kind jewelry to corkscrews featuring handcrafted designs, the options are vast, complemented by excellent food stalls serving delectable bites. It represents a perfect weekend destination within Downtown Portland.

4. Portland Electric Boat

Rent an eco-friendly electric boat at Downtown Portland’s Riverplace Marina located on SW Montgomery Street, and set forth to explore the Willamette River. The vessels operate at a maximum speed of five miles per hour and are remarkably user-friendly.

Yes, you have the opportunity to pilot the boat, play your preferred music through the onboard sound system, and bring your own picnic and beverages, or pre-order from an affiliated catering service.

Each Portland Electric Boat accommodates up to ten individuals, with a minimum rental duration of two hours. There is nothing quite like enjoying time on the river.

5. Portland Art Museum

The Portland Art Museum, located on SW Park Avenue, also houses the Northwest Film Center and boasts over one thousand square feet of exhibition space featuring forty thousand individual artworks.

Founded in the late 1800s, the museum has amassed notable collections, including remarkable works by renowned artists such as Van Gogh, Monet, and Renoir. Additionally, its collections encompass significant contributions from American, European, African, as well as various contemporary art movements.

6. Harvey’s Comedy Club

Situated along Downtown Portland’s 6th Avenue, this intimate venue features premier comedic talent. Established in 1992, Harvey’s Comedy Club has been a source of laughter for patrons ever since.

In addition to food and beverages, the venue serves up humor with top-notch stand-up performances, offering diners a delightful combination of fine cuisine and entertainment. Indulge in a comforting meal followed by a selection of cheesecake in a cabaret theater-style atmosphere for an unforgettable evening.

Do you believe you have comedic talent? Harvey’s Comedy Club hosts open-mic nights every Sunday, inviting aspiring comedians to take the stage.

7. Pioneer Place

Pioneer Place, located on 5th Avenue, stands out as an excellent destination for retail therapy in Downtown Portland. The mall comprises four interconnected blocks linked by skywalks, highlighted by a magnificent glass atrium.

Featuring over fifty stores, shoppers can find a diverse selection of products ranging from fashion and footwear to electronics and timepieces. Various dining options, including restaurants, snack bars, and cafeterias, are available on every level, complemented by a movie theater showcasing the latest releases.

8. Oregon Maritime Museum

The Oregon Maritime Museum offers a floating nautical experience aboard a sternwheel tugboat, the Portland, which is docked on the Willamette River, adjacent to Downtown’s Waterfront Park.

This tugboat, constructed in the late 1940s, stands as the last of its kind ever built in the United States and remains in operational condition. Having undergone extensive restoration, the vessel contains maritime memorabilia and offers access to the pilothouse and engine rooms.

The Portland hosts four iconic sailings each year along the river, inclusive of food and drink. Due to limited availability, it is advisable to plan ahead if you wish to participate in a voyage on this historic tugboat.

9. Shanghai Tunnels

Most cities in the United States have an intriguing, and sometimes dubious, history, and Downtown Portland is no exception. Uncover the sordid stories and hardships of the area’s past by venturing underground into the Shanghai Tunnels.

Meet your guide on Downtown Portland’s 2nd Avenue and descend into the intricate network of tunnels situated below the streets. The unsettling accounts of forced labor, the smuggling of liquor during Prohibition, and other captivating historical insights will undoubtedly provide you with chills.

The tours typically last around two hours and traverse a distance of approximately one mile. Those who experience claustrophobia are advised to reconsider undertaking this tour.

10. Roseland Theater

The Roseland Theater serves as Downtown Portland’s vibrant concert venue. Located on 6th Avenue, it is renowned for hosting performances by some of the music industry’s most prominent artists.

The venue accommodates approximately one thousand four hundred patrons in standing-room settings, alongside a limited number of balcony seats offered on a first-come, first-served basis. Expect a lineup that features chart-topping contemporary artists, bluegrass acts, and renowned DJs.

Additionally, the Roseland Theater includes Peter’s Room, a dinner-and-show venue on the ground floor, tailored for smaller, more intimate performances.

11. Jake’s Famous Crawfish

A restaurant that has been a staple in the community for over a century is certainly deserving of attention. Jake’s Famous Crawfish, located on 12th Avenue in Downtown Portland, ranks as one of the finest seafood establishments in the United States.

The menu is subject to daily changes based on seasonal seafood availability, yet it offers a remarkable selection of options. If a full dining experience is too extensive, consider stopping by during happy hour to sample their renowned bar snacks. The flavors are exceptional.

12. Pioneer Courthouse Square

Pioneer Courthouse Square, covering forty-thousand square feet, serves as the central plaza of Downtown Portland. Affectionately termed Portland’s living room, this space attracts the city’s citizens to partake in outdoor activities or attend one of the over three hundred events scheduled throughout the year.

The square features a variety of distinctive sculptures and pieces of public art, alongside a captivating cascade fountain and a milepost sign indicating distances to various global destinations.

Relax and enjoy a meal from one of the food trucks, and you may find yourself enamored with Downtown Portland to the extent of considering the purchase of a personalized brick to be placed within the square, joining the ranks of eighty thousand others.

13. The Portland Wine Bar

Experience the authentic essence of Oregon at the Portland Wine Bar, located on SW Yamhill Street in Downtown Portland. The bar specializes in wines from small vineyards, typically encompassing twenty acres or fewer, throughout Oregon and the Pacific Northwest.

Expect to see a frequently changing wine selection, as only small batches from single vineyards are offered; no blends are included, and once a wine is sold out, patrons must await the next harvest for replenishment.

The Portland Wine Bar does not serve cuisine but features a curated assortment of accompaniments to enhance the wine-tasting experience. Do not miss the truffle popcorn sprinkled with pecorino cheese—it’s an astonishing delight.

14. Waterfront Park Trail

A picturesque and tranquil means to traverse Downtown Portland is by walking along the Waterfront Park Trail. This trail also offers splendid views of the downtown district’s unique bridge architecture.

Begin your stroll at Downtown’s Steel Bridge, one among ten bridges within the district, and meander across the riverside on the paved path. Allocate time to explore the Japanese American Historical Plaza, adorned with poems and tributes to Japanese immigrants.

Continue along the pathway, passing beneath Burnside Bridge, navigating past the market, and ultimately arriving at Salmon Street Springs—a delightful interactive fountain ideal for cooling off after a leisurely walk.

15. Mother’s Bistro and Bar

For a home-like dining atmosphere, visit Mother’s Bistro and Bar, located on Stark Street in Downtown Portland.

The restaurant features a warm and inviting decor, including chandeliers, wallpaper, and grand curtains. Indulge in comfort foods reminiscent of home, such as chicken and dumplings or slow-cooked pot roast, until you are thoroughly satisfied.

You’ll feel so at home at Mother’s that you may already start planning your next visit before concluding your meal.