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City Guide: What to See, Do, and Eat in Portland, Oregon

Portland’s charms range from books, bikes, and food trucks to a vegan bar and a bagpiping unicyclist.

two men walk a dog on a trail in Forest Park in Portland, OR, photo
Photo credit
Photo: NashCo
Photo caption
Visitors to verdant Forest Park can roam miles and miles of groomed trails.

Portland is a small town—an especially creative, entrepreneurial one—disguised as a major city. Its thriving maker culture shines in the close-knit food cart scene, handmade wares at the busy Saturday Market, and frequent celebrations of area artists.

Portland's International Food Carts

More than 500 carts scattered around town in stationary “pods” draw crowds all day. The Cartopia pod in Southeast is popular with the late-night crowd, but the sprawling Cartlandia pod on SE 82nd Avenue surrounds the brick-and-mortar Blue Room Bar, where you can bring in your food cart grub to pair with your locally brewed beer.

Insider's Tip: Too cold or rainy to eat street-side? Head to Pine Street Market for a taste of the food cart culture without the weather.

Read more: Distillery Row—Portland’s Must-Drink Destination

Soccer Fandom

Forget American football: Two major-league soccer teams—the Portland Thorns and Portland Timbers—play to enthusiastic crowds in downtown Providence Park. Sing and cheer with the Rose City Riveters and Timbers Army fan groups on game days, or visit one of the city’s many soccer-centric bars—4-4-2, the Horse Brass Pub, the Toffee Club, and Beulahland stand out—to feel the love in the off-season. AAA Members receive a discount on Thorns ticket prices.

Urban Forest

Nature is just around the corner. Amble directly from the busy sidewalks of Northwest into Forest Park. The lush escape has more than 80 miles of trails for hiking, mountain biking, and horseback riding. On some Saturdays, you can take a free walking tour to learn about park history or the use of local flora in beer making.

Man dressed all in black browses at Powell's Books in Portland, OR
Photo credit
Photo: NashCo
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A reader pores over a book at Powell’s, which offers plenty of tomes to browse and buy, plus a bevy of made-in-Portland wares.

City of Books

Everybody knows about Powell’s, but it’s still a must. Browse 1 million books in the enormous block-long store. When you’re overwhelmed, retreat to the less-trafficked Rare Book Room on the third floor or the in-house coffee shop for a respite. In the Orange Room, find an array of items including Powell’s merch, embroidered patches, and Egg Press greeting cards.

Insider's Tip: Check out Portland's Old Town Chinatown and West End neighborhoods when you're down browsing.

Where to Ride

See Portland like a local—on two wheels. The bike-sharing program Biketown is easy to use, with more than 1,000 neon-orange cruisers available all over the city. Hop on the Waterfront Loop in South Waterfront at Tom McCall Waterfront Park for a casual 2.6-mile ride that takes you over the Steel and Hawthorne Bridges and along the Willamette River, or coast through the quiet Eastside Greenways for an insider’s view of Portland's neighborhoods.

Insider's Tip: Once you've cruised the Eastside Greenways, stop on N. Mississippi Ave. for artsy hangouts, stylish gifts, and a bite to eat.

Monthly Art Walks

Galleries celebrate new shows each month during First Thursdays in the Pearl District and Last Thursdays in the Alberta Arts District. In summer, the latter takes on the flavor of a street party, with live musicians and performances. Patrons mingle while browsing handmade jewelry, vintage ceramics, and unique art.

Drag queen Darcelle XV performs on stage at Darcelle XV, picture
Photo credit
Photo: NashCo
Photo caption
Octogenarian drag queen Darcelle XV wows the crowd at her eponymous club.

Year-Round Skiing and Snowboarding

The triangular mountain on Portland’s horizon is home to the only year-round skiing on real snow in the United States. Mt. Hood Meadows is its largest winter playground, but you can head to Timberline for skiing or snowboarding without consulting a calendar. The lower areas are open from fall through spring, while the upper Palmer Glacier lifts operate from May into early September.

Insider's Tip: If you prefer dirt over powder, a lift-accessed bike park is scheduled to open in summer 2019 at Timberline.

Best Bites

Happy hour means great food at fantastic value. Head to old-school RingSide Steakhouse for a $3.95 gourmet cheeseburger, Doug Fir Lounge for $1 oysters, or the vegan No Bones Beach Club for $6 “crab” cakes. Bamboo Sushi, the world’s first certified sustainable sushi restaurant, is usually a splurge—but in the early evening, it’s one of the city’s best deals.

Keep Portland Weird

Get your quirk on at the fabulous Paxton Gate curiosity shop or at Darcelle XV, where Darcelle XV— the country’s oldest drag queen—still performs her sassy routines well into her 80s. Keep an eye out for the kilt-wearing Unipiper, who plays the bagpipes (which sometimes spout flames) while riding his unicycle.

Nearby Places to Explore

Whale watching in Depoe Bay, OR

Cannon Beach, OR

Salem, OR

The ultimate Oregon Coast road trip and where to find the best local seafood along the way.

Fall in Lincoln City, OR

Eugene, OR

Willamette Valley wine in Dayton, OR

Forest Grove, OR

Oregon's scenic Gorge Drive on the Columbia River Highway.

5 Towns in Greater Portland



If you're planning on traveling to Portland, Oregon, talk to the Vacation Experts for free at AAA Travel.

This article was first published in Fall 2018. Some facts may have aged gracelessly. Please call ahead to verify information.