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Winter is Coming: Solstice Gathering & Silent Meditation Walk
Walk to the fire at the center of the labyrinth with us on Winter Solstice! It’s a quiet, meditative walk (as opposed to our exuberant Summer Solstice gatherings). Cocoa, tea, & socializing afterward.Casual, nonreligious gathering. Dress for warmth & celebration. Bring flashlights, candles, wear sturdy shoes. No dogs, smokes, or booze please.Sunday Dec. 21, 7–8 pm, corner of Hwy 242 & Hwy 20 (new Gateway Park); driveway on W. Hood Ave. Details at sisterscommunitylabyrinth.org.
The Reindeer Room Holiday Pop-up Bar at River’s Edge Golf Course
Immerse yourself in a magical holiday experience at The Reindeer Room Holiday Pop-up Bar at River’s Edge Golf Course. Transform an ordinary evening into an extraordinary experience filled with festive cocktails, tasty bites, and seasonal cheer. You won’t want to miss this merry celebration right here in Bend!DATES: Wednesday, December 3rd – Sunday, December 7th AND Wednesday, December 17th – Sunday, December 21stTIME: 4:30 PM – 9:00 PM Wednesday – Saturday
Winter Solstice Dinner at The Monkless Brasserie
On December 21st, we honor the longest night of the year—when traditions across centuries have celebrated light, love, and the returning sun.Join us for a candlelit Winter Solstice dinner at The Monkless Brasserie. Reservations are open, with dinner beginning at 4:30PM. We’ll be serving our featured Solstice special, along with the warmth of good company shared on the darkest night of the year.Winter Solstice Special: Slow Roasted Prime Rib – 10oz Choice Allen Brothers beef, house-made pop
Swingin’ Tower Christmas
<p>Enjoy the return of our family-friendly holiday salute to the liveliest songs and stories of the season. Host Mollie Tennant (“Annie”, “Cats,” “Mamma Mia,” “Les Miz”) heads a cast of local performers accompanied onstage by her husband Jim’s live 16-piece big band.</p><p>The post <a href="https://visitbend.com/event/swingin-tower-christmas/2025-12-21/">Swingin’ Tower Christmas</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Double Bubble Bars at Viaggio Wine Merchant
Double the fun in December! Our Champagne Bubble Bars are just what you need to make it through the holiday madness. We’re here for you with two full weekends of gorgeous Champagnes flowing by the flight or by the glass. Take a break and treat yourself. European small plates available too!The post Double Bubble Bars at Viaggio Wine Merchant appeared first on Visit Bend.
Paint and Sip at Bend Cider Co
Looking for a laid-back Sunday afternoon out? Come join me, your friendly local artist, for some painting and sipping fun! No pressure, just good vibes and a relaxed atmosphere.Whether you’re a seasoned artist or a total beginner, everyone’s welcome! This event is two hours, and I’ll provide the 11″x14″ canvas, all the supplies you need, and a guided tutorial.Plus, here’s the cherry on top: the first drink is on me! So come hang out, unwind, and let’s ge
Magical Markets of Merriment
<p>The 5th annual Magical Markets are here, one of Bend’s more beloved holiday markets. With rotating vendors every weekend, we have a bustling selection of curated goods to offer, as well as the fabulous Sandra Claus serving up fresh baked cookies.</p><p>The post <a href="https://visitbend.com/event/magical-markets-of-merriment/2025-12-21/">Magical Markets of Merriment</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Christmas at The Oxford: Meet Santa
<p>Get ready for some festive fun in Downtown Bend! Santa is coming to his favorite place, The Oxford Hotel, and he can’t wait to meet you on December 20-21, 2025, 10 am to 2 pm! Holiday Crafts, Cookie Decorating, and Hot Cocoa Station in Santa’s Workshop – Free for Families</p><p>The post <a href="https://visitbend.com/event/christmas-at-the-oxford-meet-santa/2025-12-21/">Christmas at The Oxford: Meet Santa</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Dirksen Derby 18 Snowboard Rally Race
The Dirksen Derby 18 Snowboard Rally Race returns to Mt. Bachelor this December 19-21, 2025! This iconic event invites the international snowboard and sit-ski communities together for an incredibly fun and memorable weekend. This event features 100% hand-crafted parallel banked slalom race courses, which have been built at a different location on the lower mountain of Mt. Bachelor every year since the Dirksen Derby’s inception in 2007.The post Dirksen Derby 18 Snowboard Rally Race appeared
Babes in Toyland
Ho ho ho’s will abound at this year’s holiday burlesque spectacular, where the whimsy of Mother Goose meets the magic of Santa’s Workshop. Join Bend Burlesque Company for “Babes in Toyland,” a playful tribute filled with flirty fairytales, vintage va-va-voom, and just enough naughtiness to land us all on the Nice List.Dress the part in your holiday finest: classic festive frocks, storybook-inspired looks, or your most playful toy-themed attire.First 20 tickets get a pre-sale discount, so don’t h
No DNB: Klippee & Wavhart
<p>Winter Solstice Party w/ Klippee & Wavhart<br />(EDM: DnB + Dubstep)<br />Webfoot Garage at Silver Moon Brewing</p><p>The post <a href="https://visitbend.com/event/no-dnb-klippee-wavhart/">No DNB: Klippee & Wavhart</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Live at the Vineyard – Jessie Leigh Christmas Concert
Nashville recording artist Jessie Leigh creates music that embodies the heart and soul of small-town America with a patriotic spirit and heartfelt lyrics. Born and raised in a rural Oregon community, Jessie’s upbringing instilled in her a deep love for her country and community, which shines through in her music. As an independent artist, Jessie is proud to say she has opened for some of the biggest names in country music, including Morgan Wallen, Luke Combs, ALABAMA, Tanya Tucker, Josh Tu
Deck the Walls – Snowboard + Ski Competition
<p>A 16’ wide x 12’ tall wall ride for a snowboard/ski competition at bend Brewing Co. The wall will be plexiglass with round metal coping on top.</p><p>// 3D rendering by @eperrett // Wall build by @black_diamond_woodworks</p><p>The post <a href="https://visitbend.com/event/deck-the-walls-snowboard-ski-competition/">Deck the Walls – Snowboard + Ski Competition</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
The Reindeer Room Holiday Pop-up Bar at River’s Edge Golf Course
Immerse yourself in a magical holiday experience at The Reindeer Room Holiday Pop-up Bar at River’s Edge Golf Course. Transform an ordinary evening into an extraordinary experience filled with festive cocktails, tasty bites, and seasonal cheer. You won’t want to miss this merry celebration right here in Bend!DATES: Wednesday, December 3rd – Sunday, December 7th AND Wednesday, December 17th – Sunday, December 21stTIME: 4:30 PM – 9:00 PM Wednesday – Saturday
Holiday Shopping Happy Hour | Oregon Spirit Distillers
<p>Take a break from holiday shopping & come enjoy all day happy hour!</p><p>The post <a href="https://visitbend.com/event/holiday-shopping-happy-hour-oregon-spirit-distillers/">Holiday Shopping Happy Hour | Oregon Spirit Distillers</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Holiday Blues Happy Hour
<p>All day happy hour!</p><p>Take a break from shopping & join us for cocktail specials!</p><p>The post <a href="https://visitbend.com/event/holiday-blues-happy-hour/">Holiday Blues Happy Hour</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Double Bubble Bars at Viaggio Wine Merchant
Double the fun in December! Our Champagne Bubble Bars are just what you need to make it through the holiday madness. We’re here for you with two full weekends of gorgeous Champagnes flowing by the flight or by the glass. Take a break and treat yourself. European small plates available too!The post Double Bubble Bars at Viaggio Wine Merchant appeared first on Visit Bend.
Magical Markets of Merriment
<p>The 5th annual Magical Markets are here, one of Bend’s more beloved holiday markets. With rotating vendors every weekend, we have a bustling selection of curated goods to offer, as well as the fabulous Sandra Claus serving up fresh baked cookies.</p><p>The post <a href="https://visitbend.com/event/magical-markets-of-merriment/2025-12-20/">Magical Markets of Merriment</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Christmas at The Oxford: Meet Santa
<p>Get ready for some festive fun in Downtown Bend! Santa is coming to his favorite place, The Oxford Hotel, and he can’t wait to meet you on December 20-21, 2025, 10 am to 2 pm! Holiday Crafts, Cookie Decorating, and Hot Cocoa Station in Santa’s Workshop – Free for Families</p><p>The post <a href="https://visitbend.com/event/christmas-at-the-oxford-meet-santa/2025-12-20/">Christmas at The Oxford: Meet Santa</a> appeared first on <a href="https://visitbend.com">Visit Bend</a>.</p>
Dirksen Derby 18 Snowboard Rally Race
The Dirksen Derby 18 Snowboard Rally Race returns to Mt. Bachelor this December 19-21, 2025! This iconic event invites the international snowboard and sit-ski communities together for an incredibly fun and memorable weekend. This event features 100% hand-crafted parallel banked slalom race courses, which have been built at a different location on the lower mountain of Mt. Bachelor every year since the Dirksen Derby’s inception in 2007.The post Dirksen Derby 18 Snowboard Rally Race appeared