Glide down a snowy mountain glistening as brightly as the stars above. Slip into dimly lit enclaves bubbling with banter. Sip smoky-spicey cocktails and nibble eclectic tapas. Seize country-hip-hop-swing moves that connect you to everyone on the dance floor. Even when the sun goes down early, there’s plenty to satisfy everyone late into the night.
Nighttime Is the New Nosh Time
Feel the warmth of Mayan and Mediterranean flavors whisk you away on a frosty January night.
San Simón
[Pictured Above] Alleys take you off the beaten path. After dark, there’s an air of intrigue. What better way to embrace the night? In Tin Pan Alley downtown, feel like a film noir character as you slip into one of the cozy wooden booths outside San Simón, with the chiaroscuro of lights strung above and the flicker of firepit tables. Slyly sip a concoction of freshly squeezed juice, spirit-lifting spirits and liqueurs made by mixologists intent on transporting you to another country in a glass. Nibble charcuterie, cheeses and briny bites of sardine and mussel conservas from Spain.
Linger here or step inside as you let loose your inner Bohemian amid the candlelit brick walls. Should some of your wishes for the evening not yet be fulfilled, consider invoking a favor from the bar’s eponymous Mayan folk deity who smokes, drinks and answers prayers that would make saints blush.
Bar Rio
Imagine burning cacti—warm and prickly—in an image Frida Kahlo might’ve painted. Then sip one: Bar Rio’s burning cacti cocktail is golden brown reposado tequila, peppery, roasted-chile Ancho Reyes liqueur, prickly pear, dark chili-rich simple syrup, lime and a rim encrusted with Tajín (ground dried chili peppers, dehydrated lime and sea salt). Revel in the lovely heat on a winter night.
Order Cuban pork sliders with prosciutto, pickles, spicy mustard, Jack cheese and Calabrian chili oil on a local Curmuffins hoagie, or get comfy with a small plate of lamb merguez sausage and orecchiette pasta, zucchini, basil, tomato, light gorgonzola cream and hazelnut-chorizo crumb. Head to Bar Rio.
Bar RBC
Make your way down the long, narrow bar or up the stairs to an intimate, loftlike space that’s perfect for sharing nighttime secrets. Time for a French Kiss—here, it’s a brandy-soaked prune shamelessly stuffed with foie gras—the start of a smooth, oaky-sweet, buttery party on your palate. Pair it with gintonic (as it’s known in Spain), and the housemade tonic’s serious bubbles will make you feel effervescent, too.
Then bring on the ocean. Bite into grilled octopus with the mild heat of piperade and a cilantro-jalapeño-mayonnaise-Parmesan aji verde. Dip salt cod fritters into aioli, and order that second libation.
Suddenly, it feels as if sea air is tousling your hair under a full moon, and your evening’s just getting started. Read more about their flagship restaurant, Rancher Butcher Chef in Bend.
Dancing in the Dark
Going out at night to dance is more than a mere pastime. “On a biological level, dance is something that connects us in a very human way,” according to Alex Reininger, a marine biologist and a dance teacher at Cross-Eyed Cricket Watering Hole where the focus is on fun and line dancing. Lessons out on the floor make line dancing easy for first-timers, whether it’s kicking it to ’90s classic country, hip-hop country or swing. All ages are welcome, no need to bring a partner, and kids’ lessons in the early evening get parents out there, too. Dancing is not only fun and noncompetitive, it’s health-boosting, said Reininger. “If we can find these fun outlets for movement, such as line dancing, you can let loose. You can be a little silly. And when we dance, we’re kind of connected in a nonverbal way. It’s very physical…similar to fish in the school. Dance is a way that we can communicate and express and tap into our creativity and connection as a species.” Dancing also taps into deep cultural roots, she added.
The vibe goes south—longitudinally speaking—at a few venues in Bend. At the vaguely equatorial lands of The Flamingo Room, the dance vibes heat up on the last Sunday of every month. Escape to a tropical foliage-packed packed hideaway with creative cocktails, where you can dance an early winter’s night away from 4 p.m. to 7 p.m. Miraculously, you’ll be in bed before the clock strikes nueve.
Nothing lets you feel the heat of Latin culture quite like the tango. Take a lesson and practice your moves Wednesday nights at the (not-so-Latin sounding) Sons of Norway Hall. The weekly sessions called Tango in Bend have gained popularity over the past decade, with teachers Tyler Haas and Emma James. Although the couple is taking a break from the endeavor, the sessions aren’t skipping a beat in 2025 with students trained to step into their role, Haas said.
On the first Thursday of every month, venture underground to The Capitol for Latin dancing that starts at 8 p.m. and goes late. Discover DJs playing a range of Latin genres or live music by BENDiciones Salsa Orchestra. It pays to heed the Flamingo’s call on social media: “What the world needs now is dance, and love, and dance.” Whether you think of yourself as a dancer or not, they encourage people to join in creating good energy—and that’s good for you, too.
Kindled Spirits
Embers swirl, scarlet flames leap and your cheeks glow beside the iron firepits. Raising a glass of rich amber single malt, you take in the toffee-almond buttered popcorn aroma. The powerful warmth and caramel finish envelop you—body, mind and soul. You’re among like-minded members of the Whiskey Club on the spacious patio wrapping around the intimate O’Kane’s at McMenamins Old St. Francis School, the 1936 Catholic school turned brewery. Peruse the members’ Whiskeys in the Shed menu for a rare special release, hard-to-find whiskey or a limited-edition McMenamins library spirit. A quarterly release of small-batch spirits rounds out members-only shenanigans, along with Whiskey Rambles: tastings and small bites with the distillers on tours of the production spaces.
The patio with strings of lights and foliaged arbors attracts dozens imbibing McMenamins creations such as Bamberg Obsession, a 2023 International Beer Awards gold-medal winner. Their Munich Helles lager’s beechwood smoked malt suits the atmosphere perfectly amid the smoldering wood, the bar’s massive, kettle-like Round Oak stove from 1896 and the aroma of cigars, also a throwback (to 2007 when O’Kane’s was grandfathered in before the state ban on smoking in bars).
Firepit studded pubs, such as Crux Fermentation Project and Crosscut Warming Hut No. 5, have popped up since O’Kanes, the OG which opened 20 years ago. Back then, old-school bartender recruits said no one would want to sit outside at night and drink when it’s cold. But they were dead wrong, and it set a trend, said O’Kanes General Manager Freestar Yost.
Hoodoo Nights: Onesies, Thriftys and Tikis
Stars up, skis out. Long known for its nighttime slope action, Hoodoo Ski Resort has more reasons to head up the mountain in Sisters after the sun has slipped below the horizon: family-and-wallet-friendly fun and a romantic option, too. This year brings the new Onesie Wednesdays—don a vintage ’80s ski suit or zip your plush unicorn, hedgehog or Minion pajama over functional gear to ski or ride 9 a.m. to 9 p.m. for $30. The tradition of Thrifty Thursdays continues: wear anything for the first chair through the last at 9 p.m. for $35.
Even in the dark, you can soak up Hoodoo’s locally owned and operated, noncorporate, family-first culture. “We’re not the biggest mountain, we don’t have the most terrain, but what we do have is a ton of heart,” said Jennifer Davis, marketing director at Hoodoo. “We don’t have a lot of rules. We get to be unique individuals, and when you come to Hoodoo, you feel that and…fall in love with us.”
Night skiing Wednesday through Saturday includes Friday Night Lights with live music, bonfires and giveaways. For the first time, the annual Enchanted Nordic Trek will be held on Valentine’s Day this year, with Nordic skiing or snowshoeing on a loop lined with tiki torches. Nibble chocolate-covered strawberries and hit the downhill trails afterward.
