Set at 3,623 feet above sea level at the edge of the Cascades, along the Deschutes River, and amidst millions of acres of beautiful wilderness comprising ponderosa pine, sagebrush, and junipers, this central Oregon town dares you to sit still. Go running, biking, kayaking, and more along the Deschutes. Hit Sparks Lake for standup paddleboarding. Rock climbing, white-water rafting, snow skiing, and more make this a year-round outdoor destination. And then there's the drinking. You can hike the Bend Ale Trail or explore local distilleries and wineries before or after hitting quality restaurants.
Follow the locals' lead and start off by running along the Deschutes River on one of nearly 30 marked trails (totaling 65 miles) within the Bend Park & Recreation District. Then grab your mountain bike and explore the 300 miles of trails in the area or stick to the road along the Three Sisters Scenic Bikeway. Ski or snowboard at Mount Bachelor, rock climb at South Sister, practice fly-fishing at the Old Mill Casting Course, or hit white water on the Deschutes. Bend has athletic events throughout the year, including the Cascade Cycling Classic, the Cascade Lakes Relay, and the Pole Pedal Paddle, which combines Alpine skiing, cross-country skiing, biking, running, and kayaking each May.
Since you'll spend most of your time outside working up a sweat, you'll need your energy. Start at Sparrow Bakery for breakfast sandwiches with a poached egg topped with avocado and arugula aioli (with or without bacon) or their quiche of the day. Want burgers, fries, and thick shakes in an old-school drive-in diner setting? Hit up Pilot Butte Drive-in. Get the "Vic Experience" with a stellar brunch at the Victorian Café, a true Bend institution where you can get the 23-ounce Proud Mary Bloody (topped with a prawn and andouille sausage skewer) and 10 different types of eggs Benedict (try the Texas Hold'em with spicy pulled pork, green chiles, and housemade ancho chile hollandaise). For pasta and pizza made with local, organic ingredients, drop by Jackson's Corner. For dinner with more of a global accent, Spork offers an eclectic menu with Latin, African, and Asian influences. If you love sushi, don't pass up gorgeous nigiri and rolls and plated dishes like wagyu carpaccio or Bangkok tofu with Thai basil at 5 Fusion & Sushi Bar from James Beard semi-finalist chef Joe Kim.
If you're into craft beer, you're in the right place. With nearly 20 craft breweries (basically one for every 4,500 people living in Bend), you have plenty to explore. The largest, Deschutes, has been brewing in Bend since 1988. Take a guided tour, enjoy beer samples, and hit the brewery's full pub. Three more to check out include Boneyard, for its Hop A Wheelie IPA; Crux Fermentation Project, where you settle in for a few pints at the tasting room in the middle of the brewery; and Ale Apotecary, where brewer Paul Arney takes cues from wine and Champagne production to age beer in oak barrels. Or hit the Bend Ale Trail and visit all 17 breweries. For something a little stronger, pop into the Oregon Spirit Distillers tasting room and check out their range of award-winning booze including vodka, genever, bourbon, and absinthe.
While plenty of Airbnb options abound here, without a doubt one of the coolest places you can stay in Bend is McMenamins Old St. Francis School Hotel. What was once a 1936 Catholic school now houses a charming and inviting 19-room hotel. Dine and drink in its brewpub from breakfast through dinner (start your day with a bacon Bloody Mary and a bacon, cheddar, fried egg English muffin sandwich), grab a beer from the brewery in the school's former basement, watch a movie in the 120-seat theater, or take a dip in the semi-enclosed indoor soaking pool among gorgeous mosaic tile. Have a larger group? Book the cottage, which can sleep six to 10 people. Note: the hotel will add an additional 41 rooms this July and August in two new buildings. For something more traditional yet still upscale, check into the Oxford Hotel. The rooms and suites at this four-diamond, 59-room downtown eco-chic boutique hotel offer high-thread-count plush bedding, locally roasted coffee, and views of the Cascades. If you really need to be next to nature, book a room at the renovated Riverhouse on the Deschutes, where you can open your door and look out on the river.
Head to Crux Fermentation Project each night 30 minutes before and 30 minutes after sundown for a killer happy hour with insane views. They offer an array of beer specials and all appetizers on their menu are $2 off. Check the website daily for sundown time. And in addition to outdoor concerts all summer at Les Schwab Amphitheater, from artists like Ben Harper, Widespread Panic, and Jackson Browne, you can hear free shows every Sunday ranging from hip-hop French Creole to Dixieland Jazz.