Raise a Glass to Cozy Bars in Bend and Redmond

During the brisk, cold evenings in the high desert, nothing sounds better than cozying up in the corner of a candlelit bar or a warm taphouse with a crackling fireplace. Whether you’re looking to sip wine with a good book, enjoy a romantic date night or find a post-adventure pint, Central Oregon offers a variety of inviting bars for the perfect refuge from the cold. Add in happy hours and locals’ deals and you’ve got even more reason to toast to a cozy night out.

Hasta Que Olvidemos

From the creators of San Simón and The Flamingo Room, Hasta Que Olvidemos is all about wine, oysters and intimate charm. Translating to “until we forget” in Spanish, the inviting spot off Galveston Avenue is one you won’t soon forget. With its romantic, tea-lit candles, cozy interior and friendly staff, it’s a delightful addition to Bend’s cozy bar scene.

The menu features a carefully curated selection of wines, bubbles and vermouth paired with hors d’oeuvres like half-shell oysters and burrata with toasted walnut and pomegranate. The late-night happy hour, called “Second Wind,” offers $9 select glasses of wine, $3 oysters, $20 bottles of champagne and $10 off caviar from 8pm to close — perfect for an indulgent nightcap.

Hasta Que Olvidemos
Open daily from 4-10pm with late-night happy hour from 8pm-close
1142 NW Galveston Ave., Bend

Crosscut Warming Hut No.

Step into Crosscut Warming Hut and you’ll feel like you’ve been transported to a cozy mountain cabin. A roaring wood stove, warm Edison bulb lighting and a rustic wood interior set the stage for relaxation. Located in Bend’s historic Old Mill District, Crosscut blends the charm of a classic mountain taphouse with a rotating tap list featuring 36 libations from craft beer and cider to craft cocktails.

Whether you’re unwinding after a day in the Cascades or simply meeting friends, Crosscut offers cabin-like warmth and craft beer diversity. Outside, a food cart lot includes Abe Capanna’s Detroit Pan Pizza, Bluma’s Chicken & Waffles and Eight Hands Sandos and Salads — ideal for pairing with your drink of choice. For extra coziness, live music lights up most Wednesday evenings and trivia night takes over on Tuesdays. Tuesday is also Local Day with $1 off drafts for locals.

Crosscut Warming Hut
Open daily from noon-9pm with Locals Day on Tue.
566 SW Mill View Way, Bend

Wayfarer Club

If you’re in Redmond, Wayfarer Club inside the SCP Hotel is your go-to spot for cozy vibes. Designed for locals and travelers alike, the tavern-style bar offers a warm atmosphere, thoughtfully crafted small plates and signature cocktails. It’s the perfect spot to relax with a drink after a hike, catch up with friends or get lost in a good book.

Happy hour, offered daily from 3 to 5pm, features half-off house cocktails, $5 draft beers and $6 glasses of wine. With its inviting ambiance and prime location in downtown Redmond, Wayfarer Club ensures that comfort and community are always on the menu.

Wayfarer Club
Open daily from 3-10pm with happy hour from 3-5pm
525 SW Sixth St., Redmond

This article appears in Jan 28, 2025 – Jan 28, 2026 and Toast! 2025.