Double Bubble Bars at Viaggio Wine Merchant
2025-12-28 14:00 - 20:00, 2025-12-27 12:00 - 21:00, 2025-12-26 12:00 - 21:00, 2025-12-21 14:00 - 20:00, 2025-12-20 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!

Mt. Bachelor National Ski Patrol Bingo Fundraiser
2025-12-28 10:00 - 13:00 | Silver Moon Brewing, 24 NW Greenwood Ave, Bend, 97701
National Ski Patrol BINGO FUNDRAISER!! Come join us for Not’cho Grandma’s Bingo with Dusty & Stacia! This is a family-friendly event. Get ready to dance, jump, hoot and holler! Drinks available for purchase! See all information and buy tickets through Eventbrite.

Boneyard Backcountry Bars
2025-12-27 11:00 - 15:00 | Mt. Bachelor, 13000 SW Century Drive, Bend, OR, 97702, United States
Gather your friends and join us at your favorite mid-mountain bar this season. We are thrilled to announce that Boneyard Beer will be returning to the Backcountry Bar at the base of Outback, bringing you the perfect blend of mountain adventures, fun activities, delectable brews, mouthwatering food, and a live DJ.

SAA 4th Friday Artwalk in Sisters, OR, All-Day 10am-7pm
2025-12-26 10:00 - 19:00 | Downtown Sisters, Sisters, OR, United States
Map, Galleries & More details at
https://www.SistersArtsAssociation.org/4th-friday-artwalks
Who? You and your friends
What? SAA 4th Friday Artwalk
Where? Sisters Oregon Downtown
When? 4th Fridays, 10AM-7pm
Cost? Complimentary-Free
Visit the SAA-Sisters Arts Association Galleries of Sisters featuring: A great time, beautiful art, good company, demonstrations, plus additional sponsoring restaurants and food venues for during and following the walk. Visit with actual artists and their work including: Fine art and contemporary paintings, photography, sculpture, ceramics, glass artistry, jewelry, and many more types of artistry.
SAA was formed in 2015 by a group of artists and supporters that believe the arts are an important part of a healthy community and an essential component of the enrichment of culture. The association exists to provide its members with a unified voice for the nurturing and enriching of the arts and to create a spirit of togetherness among artists, community and all who visit Sisters, Oregon. More at https://www.sistersartsassociation.org/4th-friday-artwalks
Downtown Sisters Oregon
222 West Hood Avenue
Sisters, OR, 97759
541-719-8581, SAA-Sisters Arts Association
events@sistersartsassociation.org
@SistersArtsAssociation

SAA 4th Friday Artwalk in Sisters, OR, All-Day 10am-7pm
2025-12-26 | Downtown Sisters, Sisters, OR, United States
Map, Galleries & More details found here.
Who? You and your friends
What? SAA 4th Friday Artwalk
Where? Sisters Oregon Downtown
When? 4th Fridays, 10AM-7pm
Cost? Complimentary-Free
Visit the Art Galleries of Sisters featuring: A great time, beautiful art, good company, demonstrations, plus additional sponsoring restaurants and food venues for during and following the walk. Visit with actual artists and their work including: Fine art and contemporary paintings, photography, sculpture, ceramics, glass artistry, jewelry, and many more types of artistry.
SAA-Sisters Arts Association was formed in 2015 by a group of artists and supporters that believe the arts are an important part of a healthy community and an essential component of the enrichment of culture. The association exists to provide its members with a unified voice for the nurturing and enriching of the arts and to create a spirit of togetherness among artists, community and all who visit Sisters, Oregon. More at https://www.sistersartsassociation.org/4th-friday-artwalks
Downtown Sisters Oregon
222 West Hood Avenue
Sisters, OR, 97759
541-719-8581, SAA-Sisters Arts Association
events@sistersartsassociation.org
@SistersArtsAssociation

Holiday Movie Nights at Tin Pan Theater
2025-12-25 18:30 - 20:00, 2025-12-25 15:30 - 17:00, 2025-12-24 18:30 - 20:00, 2025-12-23 20:00 - 21:30, 2025-12-21 15:00 - 16:30 | 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
2025-12-25 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!

Christmas Eve Dinner at Juniper Preserve
2025-12-24 16:00 - 21:00 | Juniper Preserve, 65600 Pronghorn Club Dr, Bend, 97701
Celebrate the magic of Christmas Eve in exquisite style at Iris Restaurant, where culinary artistry meets timeless holiday elegance. Indulge in a sumptuous prix fixe menu crafted by our chefs to showcase the season’s finest ingredients. Set against the stunning backdrop of Juniper Preserve, the evening promises a sophisticated dining experience filled with warmth, flavor, and festive ambiance.

Hoodoo's Wintervention 2025 in Redmond
2025-12-23 18:00 - 20:00, 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!!!

Brunch with Santa
2025-12-23 08:30 - 12:00 | Great Hall Sunriver Resort, 17600 Center Drive, Sunriver, 97707
Have brunch with Santa and all of his Sunriver friends. There will be delectable food and fun holiday characters to mix and mingle with! Now accepting online reservations for parties up to 8, by clicking the link below. For parties of 9 or more, or for general inquiries, please email greathalltraditions@sunriver-resort.com or call 541-593-3762.

Gingerbread House Decorating Party at the Blacksmith
2025-12-22 17:00 - 21:00 | Blacksmith Public House, 308 SW Evergreen Avenue Redmond, OR 97756, Redmond, OR, United States
Looking to make the season feel a little more festive? We’ve got you covered with a night at the Blacksmith dedicated to decorating your very own Gingerbread house!
Give us a call or stop in to purchase your $35 ticket, which includes your own gingerbread house, all the decorating supplies needed, and a complimentary glass of beer or wine!
Monday, December 22nd at 5 pm — This event is open for ALL ages! But make sure you claim your ticket quickly, because we will only have a limited number available for this event.

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 | 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 | 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.

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.
