With ponderosa pines towering overhead and a pristine lake stretched out before me, a martini is the last thing I'd expect to have on my mind. But here I am, hiking in Oregon's Deschutes National Forest, craving one. Sure, the views are intoxicating enough—but I can't wait to get back to Bend, one outdoorsy town in which ordering a cocktail is as natural as hitting the trails.
"Whenever I visited Bend, I kept lengthening my stay," says Jody Denton, who runs two of the town's top restaurants, Merenda and Deep. Like many recent transplants, who've helped double Bend's population in the past decade, he traded a stressful life in San Francisco for the more low-key vibe of Bend. And although his white chef's coat didn't exactly blend in with the fleece jackets typically seen around town, Denton soon learned that Bend isn't your typical place. "It's casual and friendly here, but it's not as granola as Portland," he says. "People often get so dressed up on the weekends that I sometimes think I'm in Manhattan! Bend never fails to surprise me." Indeed, a glance around Denton's dining rooms reveals patrons sipping one of the state's famous pinot noirs and sharing slices of pizza from the wood-fired oven at family-friendly Merenda. Meanwhile, across the street at Deep, young professionals in sleek leather booths order yellow-tail carpaccio and unagi sushi artfully assembled on porcelain plates.
Thanks to chefs like Denton, the region actually has more restaurants per capita than Portland. That fact, coupled with the spectacular scenery—mountains and high desert to the north, east, and west—is what has brought me here for a long weekend. Over a plate of salmon hash and eggs at The Victorian Café(the one place in town where you'll have to wait for a table), I meet Delia Paine, an artist who relocated to Bend from Seattle a few years ago with her husband, Matt, and their son, Riley. "I knew we'd made the right move when I was scrambling for a credit card in a store one day and the clerk said to me, 'You can relax, you're in Bend now,'" she recalls. Today, Delia's known around town as Bend's magnet maker; she presses vintage paper stamped with the town's logo onto magnets sold at Cascade Cottons, a clothing shop that also carries Bend-made arts and crafts.
After breakfast, Delia and Matt take me on a stroll through their River West neighborhood, where many of the town's "lunch-box" houses still stand. When Bend was a booming timber town in the early 20th century, loggers from the two local mills would build Craftsman-style bungalows during their lunch breaks. The Des Chutes Historical Museum offers self-guided walking tours of lunch-box houses in the Old Town Historic District. The former Brooks-Scanlon Mill is now the Old Mill District—a 49-store shopping complex.
Reinvention is also a prominent theme at McMenamins Old St. Francis School, which was converted into a hotel in 2004. The place pays homage to its 72-year history with black-and-white photos of founder Father Luke Sheehan on the walls and rooms named after former students. The parish hall is now a movie theater with comfy sofas and wrought-iron chandeliers, and there's even a Turkish bath on the ground floor. In the mini lobby, guests roam in fluffy robes, making their way to the soaking pool adorned with Byzantine-style tiles.
McMenamins also happens to have prime placement: It's a quick walk to Northwest Wall Street, the town's once-sleepy main drag. Today, dusty old car dealerships and hardware stores downtown have been replaced with boutiques, cafés, and bars such as Deschutes Brewery & Public House. Of the six microbreweries in town, Deschutes is the most popular, serving ales and porters made from regional hops, along with fancy bar food. I order the elk burger with smoked cheddar (the region's large herds of elk are so prolific that the local semipro baseball team is named the Bend Elks) and wash it down with a pint of Cascade Ale. After that, I'm definitely full, but I still can't resist the pull of Goody's, a candy and ice cream shop with checkered floors, antique soda fountains, and an apron-clad staff. I buy a bag of chocolates, including dipped Ruffles chips and almond clusters, and head for my date with tour guide John Flannery.
Flannery is the town's unofficial ambassador (at least that's what his hat says) and the owner of Bend Cycle Cab. His job is to career about in a two-seat pedicab and regale visitors with his vast knowledge of local lore, interspersed with hilarious asides. At 14th and Galveston, he circles around "Phoenix Rising", an orange-metal bird sculpture planted in the center of a roundabout. "People really disliked it at first and wanted it taken down," he says. "Now we call it 'The Flaming Chicken.'" The tour is an adventure all the way to the end, when he makes a final stop at another artwork, "Cascade Landscape", which features blocks of steel scattered about a plot of wood chips. If Flannery had his way, he tells me, the work would be renamed "Alien Turds". I agree to pose for a photo and follow his directions to gesticulate as if there's a UFO in the sky.
Local characters like Flannery give the town its offbeat charm, but the great outdoors is the main draw. The sand-colored volcanic rock faces (one of which is 550 feet high) at Smith Rock State Park attract climbers from all over the world. In the summer, Wanderlust Tours offers canoe trips to the region's Cascade Lakes near Mount Bachelor; one tour includes a moonlit dinner on the shore.
Since I'm here in October, when it's a little too cold to canoe, I sign up for Wanderlust's hike within the caldera of a dormant volcano in Newberry National Volcanic Monument. I trek across the peaks and plateaus of black, glassy obsidian, the remains of a lava flow that covered this enormous patch of earth about 1,300 years ago. When I reach Paulina Lake, my tour guide, David, is handing out strands of old-man's beard, an edible lichen that hangs loosely from the trees. It's surprisingly tasty, but I'm glad to know that there are other culinary options just around the bend.
Bend Cycle Cab
541/408-6363, bendcyclecab.com, from $30
800/962-2862, wanderlusttours.com, from $42
McMenamins Old St. Francis School
700 NW Bond St., 541/382-5174, mcmenamins.com, from $114
900 NW Wall St., 541/330-2304, pizza from $12
821 NW Wall St., 541/323-9841, sushi from $7
The Victorian Café
1404 NW Galveston Ave., 541/382-6411, salmon hash $13
Deschutes Brewery & Public House
1044 NW Bond St., 541/382-9242, elk burger $12
957 NW Wall St., 541/389-5185
Des Chutes Historical Museum
129 NW Idaho Ave., 541/389-1813, , $5
Smith Rock State Park
Newberry National Volcanic Monument
815 NW Wall St., 541/306-6071
Old Mill District
SW Powerhouse Dr., 541/312-0131