Double Bubble Bars at Viaggio Wine Merchant
2025-12-21 14:00 - 20:00, 2025-12-20 12:00 - 21:00, 2025-12-19 12:00 - 21:00 (America/Los_Angeles) | Viaggio Wine Merchant, 210 SW Century Drive, Ste 160, Bend, 97702
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!

Photos With Santa
2025-12-21 14:00 - 17:00 | Blacksmith Public House, 308 SW Evergreen Avenue Redmond, OR 97756, Redmond, OR, United States
Join us on Sunday, December 21st from 2pm -5pm to meet the man himself!
After Bingo! For Brightside, Santa will be arriving in Redmond, Oregon, and he can’t wait to take some photos with you! The event is available for all ages, and dogs are welcome too!
Bring your own camera or cell phone, and enjoy your photos free of charge.
Be sure to try our delicious Christmas Cocktail menu with drinks like our Spanish Coffee adaptation – the Santa’s Mistress – or a spiked Crown Chocolate Hot Chocolate – the Mrs. Claus – or grab a couple of regular hot chocolates for the kids!

Somewhere That's Green's Magical Markets of Merriment
2025-12-21 10:00 - 17:00, 2025-12-20 10:00 - 2025-12-21 17:00, 2025-12-14 10:00 - 17:00 | Somewhere That’s Green, 1017 NE 2nd St, Bend, 97701
Come meet Sandra Claus, grab a freshly baked cookie, a butterbeer or hot cocoa, and get into the magical mood of winter! New makers each weekend!
Nov 29/30, Dec 6/7, Dec 13/14, Dec 20/21.
10 am-5 pm

Dirksen Derby 18 Snowboard Rally Race
2025-12-21 08:00 - 16:00, 2025-12-20 08:00 - 16:00, 2025-12-19 08:00 - 16:00 | Mt. Bachelor, 13000 SW Century Drive, Bend, OR, 97702, United States
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.
Photo courtesy of the Dirksen Derby | Artwork by Adam Haynes
More About the Dirksen Derby
The Dirksen Derby takes place December 19 through 21, an event hosted at Mt. Bachelor that brings together more than 500 riders in 24 divisions to showcase skill, and build camaraderie and connection. Founded in 2007, the Derby began as a fundraiser for Tyler Eklund, a Bend snowboarder who was paralyzed as a teenager after a fall at a national competition that year. Since then, the event has benefited other causes and nonprofits, including Oregon Adaptive Sports, ProtectOur Winters, and the Central Oregon Avalanche Association.

“I know that donations mean a lot to the individuals and nonprofits that receive them,” founder Josh Dirksen said.
“But I also realize they need more than just money. They need awareness, kindness, understanding, volunteer support and a strong connection to the greater community.”

In the past, the Derby has registered racers from 6 to 76 years old, whether professionals or the playful—categories are elite, yogi, mini-shred, “older & wiser” and more. But, “One of my biggest joys each year is seeing our original inspiration (and fundraising recipient), tetraplegic rider Tyler Eklund, race down our Green course together with Kendall Cook from Oregon Adaptive Sports,” Dirksen said. See more at dirksenderby.com.

Deck the Walls at Bend Brewing Co.
2025-12-20 17:00 - 22:00 | Bend Brewing Co, 1019 NW Brooks St, Bend, 97701
A 16’ wide x 12’ tall wall ride for a snowboard/ski competition @bendbrewingco. The wall will be plexiglass with round metal coping on top. // The timing is awesome because it will be happening during the @dirksenderby weekend. // 3D rendering by @eperrett // Wall build by @black_diamond_woodworks

Poetry Night at Lone Pine
2025-12-20 17:00 - 19:00 | Lone Pine Coffee East Side, 1462 Cushing Dr. Ste 160, Bend, 97701, United States
Experience a night of poetry at Lone Pine during Apèro Hour. Listen to spoken word, share your own verses at the open mic, and savor wine, beer, bites, and coffee. All ages are invited.

The Amaterra Wine Club Experience
2025-12-20 15:00 - 17:30 | Amaterra Kitchen + Social Club, 909 NW Bond St, Bend, 97703
Step inside the newly renovated Wine Lounge private event space—usually reserved for members only—for a special evening of live oyster shucking and tasting our vibrant Blanc de Noir. This event is open to everyone, giving you a taste of what it’s like to be part of the Amaterra Wine Club community.

Enjoy our special offer of $20 for a glass of bubbles and 4 freshly shucked oysters, with additional oysters just $2 each. Savor local flavors with snacks from our happy hour menu and mingle with fellow guests in a welcoming, community-focused atmosphere in downtown Bend.
Guests are encouraged to make a dining reservation afterward to enjoy the full Amaterra experience. Join us to connect, celebrate local fare, and experience the Amaterra community firsthand.

Santa Comes to the Oxford Hotel
2025-12-20 10:00 - 14:00 | Oxford Hotel, 10 NW Minnesota Ave, Bend, Bend, OR, 97703, United States
Santa is making a special stop at the Oxford Hotel and he can’t wait to meet you! Bring the little ones for complimentary crafts, cookie decorating, letters to Santa, and a hot cocoa bar! Indulge in the season’s delights with scrumptious food and beverages available for purchase at ROAM.

Hoodoo's Wintervention 2025 in Redmond
2025-12-19 18:00 - 20:00 | Wild Ride Brew, 332 SW 5th St, Redmond, 97756
Hoodoo’s about to have a Wintervention…You snooooow ready? It’s the deepest Snow Series Giveaway in the Northwest and it’s coming to a venue near you!!! Hoodoo’s dumpin’ over 100K in prizes this season…lift tickets,skis,boards, gear, snow and more. Games, Trivia, Movies, Bloopers and antics hosted by Harold the Hodag and his friends Yeti and Sas…Get all the details on upcoming events at hoodoo.com
11/13 Wintervention/ Sisters *Thursday @ Three Creeks
Presented By: Hillside Ski and Sport | Hosted By: Backyard Media: Address: 721 Desperado Ct Sisters, OR 97759
11/18 Wintervention Redmond *Tuesday @ Wild Ride Brewing
Presented By: Hillside Ski and Sport | Hosted By: Backyard Media: Address: 332 SW 5th St, Redmond, OR 97756
11/25 Wintervention Bend *Tuesday @ SunRiver Brewing-Eastside
Presented By: Tactics Boardshop | Hosted By: Backyard Media: Address: 1500 NE Cushing Dr, Bend, OR 97701
12/4 Wintervention/ Sisters *Thursday @ Three Creeks
Presented By: Hillside Ski and Sport | Hosted By: Backyard Media: Address: 721 Desperado Ct, Sisters, OR 97759
12/9 Wintervention Redmond *Tuesday @ Wild Ride Brewing
Presented By: Hillside Ski and Sport Hosted By: Backyard Media: Address: 332 SW 5th St, Redmond, OR 97756
12/16 Wintervention Bend *Tuesday @ SunRiver Brewing-Eastside
Presented By: Tactics Boardshop | Hosted By: Backyard Media: Address: 1500 NE Cushing Dr, Bend, OR 97701
12/18 Wintervention/ Sisters *Thursday @ Three Creeks
Presented By: Hillside Ski and Sport Hosted By: Backyard Media: Address: 721 Desperado Ct, Sisters, OR 97759
12/23 Wintervention Redmond *Tuesday @ Wild Ride Brewing
Presented By: Hillside Ski and Sport | Hosted By: Backyard Media: Address: 332 SW 5th St, Redmond, OR 97759
12/30 Wintervention Bend *Tuesday @ SunRiver Brewing-Eastside
Presented By: Tactics Boardshop Hosted By: Backyard Media: Address: 1500 NE Cushing Dr, Bend, OR 97701
SKI YOU SOON!!!

Vintage Rendezvous Clothing Pop-Up
2025-12-19 16:00 - 20:00 | Crux Fermentation Project, 50 SW Division St., Bend, OR, 97702, United States
Step into style and sound at our Vintage Rendezvous Clothing Pop-Up happening at Crux Fermentation on Friday, December 19 from 4–8 PM! Discover unique vintage to modern pieces while soaking in an incredible live atmosphere featuring beats from vinyl DJ Verndon and smooth saxophone vibes from Carson Hackbart. Grab a drink, browse the racks, and enjoy an evening of music, community, and timeless fashion.

Dirksen Derby at Mt. Bachelor - CANCELED
2025-12-19, 2025-12-19 - 2025-12-21 | Mt. Bachelor, 13000 SW Century Drive, Bend, OR, 97702, United States
The goal of the Dirksen Derby is to bring the Snowboard and Sit-Ski communities together for an incredibly fun and memorable weekend full of fast race times, strong friendships and fond memories while donating money to good causes. This timed event features a hand-crafted parallel banked slalom race course, with two 30-second courses designed for riders of all abilities.
The Dirksen Derby is an annual gathering of snowboarders, sit-skiers, artists, musicians, filmmakers, friends and family from all around the globe. With categories ranging from Mini Shred to Raja (70+), plus adaptive, trans & non-binary, and elite divisions, this inclusive event celebrates competition, camaraderie, and the pure joy of riding.

Jurassic Quest at Deschutes County Fair and Expo Center
2025-12-19 - 2025-12-21 | Deschutes County Fair & Expo Center, 3800 SW Airport Way, Redmond, OR, 97756, United States
This year’s show features all the excitement of Jurassic Quest with a festive holiday twist. Families can walk among 80+ life-size, animatronic dinosaurs, enjoy interactive exhibits, fossil digs, dino rides, live shows, and get up-close with our baby dinosaurs and expert trainers — all transformed for the season with:
Christmas-themed dinosaur backdrops
Photos with Santa
Elf on the Shelf appearances
Holiday décor and seasonal installations throughout the venue
Festive photo ops perfect for family holiday cards
Event Details:
December 19–21
Deschutes County Fairgrounds Expo Center – Redmond, OR
Tickets & info here.

Holiday Movie Nights at Tin Pan Theater
2025-12-18 18:30 - 20:00 | Tin Pan Theater, 869 Northwest Tin Pan Alley, Bend, OR, 97703, United States
Whether you’ve been naughty or nice, we know you’ve been waiting all year… Our Holiday Movie lineup has arrived! Tickets are live and already selling quickly, so secure your seats now!
Die Hard 12.11 at 6:30 pm, 12.23 at 8 pm
Home Alone 12.21 at 3 pm, 12.25 at 3:30 pm
Love Actually 12.04 at 6 pm, 12.24 6:30 pm
How the Grinch Stole Christmas 12.25 at 6:30 pm
The Holdovers 12.18 at 6:30 pm

Winter Nights at High Desert Museum
2025-12-18 16:00 - 19:00 | High Desert Museum, 59800 South Hwy 97, Bend, OR, United States
The weather outside is getting colder. There’s frost on the ground and a nip in the air. Winter is coming!
Join us after hours in the warmth of the Museum for festive fun every Thursday in December (excluding Christmas Day) when Winter Nights returns. Here’s what to expect each evening:

Cookie decorating, storytelling and dance parties.
Special hands-on activities for kids of all ages, including scavenger hunts.
Regional beverage tastings from Sunriver Brewing, Cascade Lakes Brewing, Avid Cider, Laurel Ridge Winery and more.
A festive photo booth to create your fun family portrait.
Delicious snacks and dinner items at the Rimrock Café.
Holiday shopping at Silver Sage Trading with complimentary gift wrapping.

Each Thursday evening includes a theme — from wearing your coziest socks to donning that silver track suit. Enjoy music and crafts, explore exhibitions, munch on tasty treats, sip and mingle with friends and celebrate the season. Get your tickets early and save!

Hoodoo's Wintervention 2025 in Sisters
2025-12-18 08:00 - 17:00 | Three Creeks Brewing, 721 S Desperado Ct, Sisters, OR, 97759, United States

Hoodoo's Wintervention 2025 in Bend
2025-12-16 18:00 - 20:00 | Sunriver Brewing Co.

Beer Dinner with Lucky Woodsman and Terranaut Beer
2025-12-16 17:30 - 21:30 | Terranaut Beer Taproom, 20750 High Desert Lane, STE 106, Bend, OR, 97701
Luckey’s Woodsman x Terranaut Beer
Join us for a special Holiday Craft Beer Dinner featuring Terranaut Beer, where bold winter flavors, curated pairings, and chef-crafted dishes come together for an unforgettable evening. This six-course experience blends seasonal ingredients, creative technique, and exceptional brews that highlight the spirit of the season.
This isn’t just dinner—it’s a full sensory celebration designed for beer lovers, food enthusiasts, and anyone looking to savor something truly memorable before the holidays.
Craft Beer Meets Vinyl Culture:
Terranaut Beer is known for spinning sweet jams straight from their legendary vinyl collection. For this event, every course is paired not only with a signature Terranaut brew—but also with a curated vinyl vibe that enhances the flavor profile, mood, and moment.
Think of it as a multi-sensory pairing:
Beer + Food + Music = The Ultimate Holiday Experience
Perfect Pairings:
Each dish is thoughtfully matched with a featured Terranaut beer, chosen to complement the flavors of the course and the vinyl soundtrack spinning alongside it.
Seasonal Craft Cuisine:
Enjoy a winter-inspired menu built around warming spices, forest elements, bright berries, and comforting textures.
Beer Storytelling:
Learn about the artistry and inspiration behind each Terranaut offering as you sip your way through the night.

Fireside Festivities at Discovery Corner
2025-12-16 16:00 - 19:00 | Discovery Corner Plaza, 1125 NW Ochoa Drive, Bend, OR, 97703, United States
Step into the holiday magic with free hot chocolate from Sparrow Mercado, carolers from the Youth Choir of Central Oregon, and a special appearance by the big guy himself, Santa!
To celebrate the giving spirit, we will also be collecting non-perishable food donations (canned foods, boxed meals, etc.) for The Giving Plate. Everyone who brings at least one donation will be entered to win a gift basket of holiday goodies.
Fun for all ages!

Seeds of Intention: Solstice Garland Workshop
2025-12-15 18:00 - 20:00, 2025-12-15 08:00 - 17:00 | The Open Arts Center, 999 NE 2nd. St., Bend, 97701
Celebrate the winter solstice and the arrival of the darker months with a creative, mindful, intention-setting evening of floral play. In this hands-on workshop, you’ll explore seasonal botanicals and design your own wall-hangings, along with a guided activity to plant seeds of intentions to germinate during the dormant season and to grow and flourish as we cycle towards the increasing light.
Participants will leave with their beautiful creations, clarity about intentions and growth, and seeds to plant during warmer months.
No prior experience is needed—just bring your curiosity and creativity!
What’s Included:
All materials for your floral creation
Guidance from our instructors
A cozy, welcoming space for creativity and reflection
Spaces are limited—reserve your spot today and bring the spirit of the solstice into your home!
$30 per person | Only 15 spots available

Menorah Lighting in the Old Mill District
2025-12-14 16:00 - 18:00 | Old Mill District, near 475 SW Powerhouse Drive, Bend, OR, 97702, United States
Chabad of Central Oregon will light the Menorah in the Old Mill District. Gather for music, performances, delicious treats, and a joyful ceremony that marks the beginning of the Festival of Lights.
🌟 This annual celebration welcomes everyone to share in a moment of unity, hope, and community as the Menorah shines bright.

Kids’ Entrepreneur Holiday Market
2025-12-14 13:00 - 16:00 | Elks Lodge, 63120 Boyd Acres Rd, Bend, 97701
The Kids’ Entrepreneur Market is an entirely kid-run, eco-friendly market, for ages 7-17 to learn entrepreneurship by creating and selling their own products and services. This is a real-world experience that allows children to be creative, build confidence, learn skills beyond the classroom – and above all, have fun! Handmade gifts, artisan crafts, artwork, food, drinks, jewelry, and more. Come support young entrepreneurs in our community! FREE to attend. $15-$30 to participate.
