Bend, Oregon

Best For: Multisport junkies with a taste for microbrews 

Executive summary by darmansjah

The biggest town on this list, Bend is a fast-growing, adventure paradise of more than 76,000 people in central Oregon that happens to have the region’s premier ski area, Mount Bachelor, 22 miles west up the road. If you ever dream of skiing in the Pacific Northwest, Bachelor is the kind of mountain you dream about. A 9,000-foot stratovolcano lined with high-speed quads and skiable down every side, it’s a huge, diverse area which, being on the drier, east side of the Cascades, has lighter snow than the Pacific cement that coats most mountains in the region. Beginner and intermediate runs are scattered throughout Bachelor, and some of the groomers are world-class. But with fully 60 percent of the alpine terrain rated black or double-black, experts will get the most from the mountain. From the summit, adventuresome skiers and boarders can jump cornices into the blasted-open summit crater or head for the mountain’s backside of wide-open, backcountry-style double-blacks. Freestyle terrain is excellent, with two halfpipes (18 and 12 feet tall), and a nearly mile-long terrain park.

While Bend itself may lack the cozy, world-unto-itself feel of small ski towns, it makes up for it with lodging options for any budget, a stupendous selection of hip restaurants, and nine microbreweries within walking distance of each other in the city’s downtown (there’s a reason it’s called “Beervana”). Bachelor keeps the lifts running through Memorial Day, so if you come anytime after mid-winter you can ski up on the mountain in the morning and hike or mountain bike in the lowlands in the afternoon.

Ask a Local

Twenty-year Bend local Gerry Lopez, formerly of Hawaii, is one of the most famous surfers in the world and a surfboard manufacturer, writer, and motivational speaker. A dedicated snowboarder, Lopez moved here because of Bachelor’s snowboarding terrain. Here are his recommendations.

Best Digs

Budget: Rainbow Motel

Swank: The Mountain Suites at the Oxford Hotel

Best Eats

Cheap: Parilla Grill

Gourmet: The Blacksmith Restaurant

Best After-Ski Party Spot

Deschutes Brewery

Best Rest-Day Activity

Shopping at the Old Mill District or yoga at one of Bend’s many good studios

Bend’s Classic Ski Run

Thunderbird under the Pine Marten Express chairlift