Photo: Cyclists on bridge

Cyclists cross the Hawthorn Bridge heading east during the afternoon commute in Portland.

Photograph by Jan Sonnenmair, Aurora Photos

Pop. 575,930
GPS: 45°32N; 122°39W

Portland is surrounded by some of the best outdoor escapes in the country: Year-round skiing at Mount Hood is two hours east, wind- and kite-surfing on the Columbia an hour east, surfing the Pacific an hour west, and countless waterfall-laced hikes in every direction. But even more impressive are the adventure options within city limits, starting with Forest Park, the biggest urban forested area in the country; the 5,100 wooded acres (2,064 wooded hectares) have more than 70 miles (113 kilometers) of hiking trails, including an epic 30-mile (48-kilometer) loop called the Wildwood Trail. The city is also one of the most bike-friendly in the U.S., with more than 171 miles (275 kilometers) of bike lanes (and more soon on the way) and a 40-mile (64-kilometer) loop trail system (www.40mileloop.org).

PLAY

Experience Portland’s enviable cycling infrastructure on Pedal Bike Tours three-hour “Downtown Portland” tour, which loops past the 18th-century cast-iron buildings of Old Town, through Chinatown and the trendy Pearl District, along the Willamette River waterfront, and across two of the city’s eight bridges ($49, including bike rental; www.pedalbiketours.com). Owner and guide Todd Roll throws in plenty of restaurant and brewery recommendations, too—and you’ll need them: Portland has more breweries than any other city in the country (www.portlandbeer.org). Our pick is Amnesia Brewing, a laid-back joint in an old converted warehouse on hip Mississippi Street; their Copacetic IPA might be the best beer in the whole city ( 1 503 281 7708). West of town, Scappoose Bay Kayaking offers guided tours of the wetlands circling the city. Sign on for an afternoon tour and spot bald eagles, beavers, and herons ($45 for three hours; www.scappoosebaykayaking.com). Back in Portland proper, a stop in at the sprawling Powell's Bookstore—the biggest in the country—is a must (www.powells.com).

EAT

For lunch, you’ll find the best cheap eats at one of Portland’s famous food carts (www.foodcartsportland.com). Clusters of stands and trailers are set up throughout the city—in parking lots, green spaces, and along the waterfront—and serve up everything from vegan Mexican burritos to traditional goulash, all fresh and hot for $5 to $7. For sit-down occasions, Clyde Common, housed in the Ace Hotel, has tasty small plates made from regionally-grown ingredients (www.clydecommon.com). Late night, join the line queuing up outside of Voodoo Doughnut on Southwest Third Avenue; the quirky joint pops out fresh, inventive pastries 24-hours-a-day. Our picks: The old dirty bastard, a chocolatey, peanut buttery piece of fried heaven and, for the truly brave, the sinfully rich bacon maple bar—playfully nicknamed “the B.M.,” because you should only have one a day (www.voodoodoughnut.com).

SLEEP

The Kennedy School is an old grade school that’s been smartly remodeled into a hotel, with an onsite brewery, movie theater (flicks are free for hotel guests), soaking pool, and a pub (doubles from $109; www.kennedyschool.com).

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