We love Bend. Bend is great. The Bend Ale Trail—15 breweries and counting—offers plenty to toast. Delish Donuts has perfected the classics. Concerts at the Les Schwab Amphitheater (this year’s lineup somehow bridges Ween and the Steve Miller Band) are a perfect union of music and mountainscape. But why venture all that way just to stay in a city? Here are some nearby spots to explore.

Day Trips

Start with a morning hike on the Tumalo Falls and Double Falls Trail, two level miles along the Deschutes leading to the top of Tumalo Falls. Pack a lunch for a riverside picnic at Tumalo State Park, and plan for dinner at the dining attraction of Tumalo (population under 600): the 26-year-old, legendary steak house Tumalo Feed Company, where kids who clean their plates choose a prize from a saddlebag of goodies.

For a boozier adventure, follow eggs Benedict at Redmond’s One Street Down Café with a session at Faith, Hope, and Charity Winery, a husband-and-wife-owned vineyard near Terrebonne with majestic views of the Three Sisters. Try the Moulin Rouge at downtown Redmond’s Red Martini before grabbing dinner at Oregon’s smallest commercial brewery, Smith Rock.

Go full Old West in Sisters, where it’s hard to find a building that doesn’t look straight out of a John Wayne flick—even the four-screen Sisters Movie House was built to look like an old barn. Grab a cup of joe from the original Sisters Coffee Company, whose popular Portland outpost has caffeinated the Pearl since 2011, and get a bear claw or maple bar from Sisters Bakery, the town’s best. Three Creeks Brewing Co fills growlers to sneak on your wildflower picnic along the Metolius River. Set in a former hotel built in 1912, the beautifully restored Sisters Saloon promises “contemporary cowboy grub,” complete with plenty of taxidermy above the bar. —LK

Touch the Monkey

A famed destination for climbers the world over, Smith Rock State Park also offers plenty for those who only use carabiners for keychains. The Crooked River cuts its way through towering crags of basalt and tuff as you set off on Misery Ridge Trail, a 3.7-mile loop nowhere near as torturous as the name suggests, and rewards with views of more than a half-dozen Cascade peaks. Plus, you’ll be too distracted by the entertainment to feel pain: all around you, Smith’s sinewy athletes claw their callused way up cliffs, including the unmissable 350-foot spire known as Monkey Face. —RJ

Lodge Life

Overlooking a ribbon of lake deep in the Deschutes National Forest near Sisters, the loggily grand Suttle Lodge is arguably historic. Yes, a lodge has been situated here for almost a century. Just not this lodge. This lodge was built in 2005; a decade later, a who’s-who of Kinfolk-ish Portland chicsters took over: draping custom Pendleton blankets across the nice, firm beds, whipping up highballs and custom-welded bookshelves, kitting out the rustic cabins with Traeger grills and retro lawnchairs. The result feels a little bit country, a little bit freak-folk and buttered salmon rolls. Cabins from $88, lodge rooms from $193.—RD

Beer (But Not Bud; Never That!) in Prineville

The city council may have made it harder to buy marijuana, but at least Prineville locals are getting a second brewpub. At Ochoco Brewing (formerly Solstice), open since 2011, overheard bar talk about having to “breed or slaughter all your girls” is a reminder that not everyone here works at the local Facebook data center—ranchers abound, evidenced by the nearby Breese Ranch beef on the menu. A block away, Crooked River Brewing spent the spring waiting for final permits for its in-house brewery, stocking the taps in its warehouse rec-room space with guest beers originating from Bend to Bavaria. —MS

Drive Smart Out There

Asked if there are rookie mistakes city folk make when they leave Portland’s cozy street grid, Steven Hooper of Bend’s Consolidated Towing assures me: “Local people do the same things.” He says everyone should carry a shovel when driving in snow and use their heads before turning onto a dirt road. Mind the ruts and potholes, and watch for mud. “The second you go on a dirt road, you’re taking your ability to get yourself out of there into risk,” he says. “It can become shockingly expensive and a huge ordeal to get people out of some situations.” How shocking? A tricky extraction can run into the thousands—or, like one poor fellow who called Consolidated this winter, you might have to leave your car where it is until the snow melts. —MS

Distance from Portland: Sisters, Tumalo, Smith Rock, and Prineville are all about 3 hours away.