The Barn in Sisters Holiday Market
2025-12-07 11:00 - 16:00 (America/Los_Angeles) | The Barn in Sisters, 171 E Main Ave, Sisters, 97759, United States
Get into the holiday spirit at the Holiday Makers Market! From 10 AM to 4 PM at The Barn. Shop local and find the perfect gifts for everyone on your list.

Kindred Holiday Market
2025-12-07 11:00 - 16:00 | Spork, 937 NW Newport Ave, Bend, 97703
Kindred Market – a community-centered holiday gathering of local makers and handcrafted goods – returns December 7th at Spork Bend.
Shop unique gifts, meet the artisans behind them, and celebrate shopping locally this season. Donations collected for Latino Community Association. 11–4 PM | Free entry

Bevel Holiday Market
2025-12-07 12:00 - 16:00 | Bevel Craft Brewing, 911 SE Armour Rd, Bend, OR, 97702, United States
Shop with 11 different vendors each day. Donate to Toys for Tots and enjoy a festive beverage.
Santa will be here 2-4pm both days!

Summit and Bend High School Theatre Present: Head Over Heels
2025-12-07 14:00 - 16:00, 2025-12-11 19:00 - 21:00, 2025-12-12 19:00 - 21:00, 2025-12-13 19:00 - 21:00 | Summit High School Theater, 2855 NW Clearwater Dr, Bend, 97703, United States
Summit High School and Bend Senior High School unite for their first-ever joint production with Head Over Heels, the irresistible jukebox musical set to the chart-topping hits of The Go-Go’s. Inspired by Philip Sidney’s The Countess of Pembroke’s Arcadia, the show follows the royal court of Arcadia after a prophecy from the Oracle of Delphi warns that the kingdom will lose its “Beat,” the life force that sustains its prosperity. Determined to outwit fate, King Basilius leads the court on a wild journey through the woods where mistaken identities, unexpected romance, and gender-expansive disguises turn tradition on its head. The result is a vibrant celebration of authenticity, acceptance, and love.
Featuring high-energy vocals, a live rock band, and Ancient Greece-meets-the-1980s design, this production invites audiences to groove along to iconic songs including “We Got the Beat,” “Our Lips Are Sealed,” “Vacation,” Belinda Carlisle’s “Heaven Is a Place on Earth,” and “Mad About You.”

Cascade Chorale's Holiday Magic - A Season's Journey
2025-12-07 15:00 - 2025-12-08 17:00 | Tower Theatre
Under the masterful direction and artistry of James W. Knox, this concert offers not just a collection of carols and choral works, but a meditative progression through the themes of mystery, wonder, joy, and community that define this time of year. Come share in the joy at the Tower Theatre on December 6 and 7 from 7-9 p.m.

Christmas Tree Lighting in Downtown Bend
2025-12-07 17:00 - 19:30 | Downtown Bend, Bend, OR, United States
Celebrate one of Downtown Bend’s most magical traditions!
Join us in Brandis Square for an evening full of holiday cheer, music, and community.
5 pm – 7:30 pm
Sunday, December 7th
Visit with Santa
Enjoy performances from local choirs
Tree Lighting at 6:00 PM
Bring your loved ones, soak in the festive atmosphere, and help us kick off the holiday season as we light the Downtown Bend Christmas Tree.

Holiday Lights & Cookie Run With FootZone
2025-12-10 17:30 - 19:00 | FootZone Bend, 842 Northwest Wall Street, Bend, OR, 97703, United States
Join us for an evening of running, cookies and holiday cheer at our annual FootZone Cookie Run! Bring your friends, your festive spirit and, if you’d like, your best homemade cookies.
We’ll kick things off with a 3 mile run highlighting some of the neighborhood’s best holiday lights and decorations, all within close proximity. There will also be a shorter course for those interested.
After the run, warm up with hot cocoa and cookies! We’ll also hold our annual Cookie Contest, with judging based on taste, visual appeal and overall holiday vibe. Email col@footzonebend to enter the contest. The winner gets bragging rights and a $25 FootZone gift card!

Winter Nights at High Desert Museum
2025-12-11 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!

Holiday Movie Nights at Tin Pan Theater
2025-12-11 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

Holiday Lights Paddle Parade
2025-12-12 16:00 | Tumalo Creek Kayak & Canoe, 805 SW Industrial Way, Bend, OR, 97702, United States
Light up the Deschutes River at dusk at the annual Holiday Lights Paddle Parade. Adorn your kayak, canoe or paddleboard with festive holiday lights. Spectators can bundle up and catch the illuminated spectacle as it floats through the Old Mill District.

A Blue Christmas: Ornament Painting Workshop
2025-12-12 19:00 - 20:30 | Pine & Prism, 856 NW Bond St. Suite 202, Bend, 97701
Join professional artist, Michelle Schultz, for an enchanting Ornament Painting Workshop!
This is your invitation to pause amidst the holiday hustle and embrace a moment of tranquility and creativity. In our cozy, candlelit space, let your imagination run wild as you paint beautiful ornaments, sip wine, and set meaningful intentions for the season. This workshop is a perfect opportunity to reconnect with yourself and celebrate the quiet magic of the holidays.
-All materials, beverages, and vibes provided.
Spots are limited, so reserve your spot now and indulge in an intimate, creative escape that nourishes your spirit.
No Experience Necessary.
Age Limit 21+

St. Lucia Day Celebration at Fika Sisters Coffeehouse
2025-12-13 07:00 - 13:00 | Fika Sisters Coffeehouse, 201 E Sun Ranch Dr suite c, Sisters, 97759, United States
Beginning early morning, celebrate “St.Lucia” at Fika Sisters Coffeehouse. Ring in the start of Christmas in the form of candlelight, coffee discounts and the sounds of local harpist, Becky Smith. Then, enjoy local artists, vendors and Christmas storytelling. All day, there will be cookie decorating and St. Lucia Day crafts with yummy baked goods and gingerbread lattes to be delighted by all!

The Locavore Holiday Gift Faire
2025-12-13 09:00 - 15:00 | 61980 Skyline Ranch Road Bend, OR 97703 United States, United States, Skyline Ranch Road Bend, 61380
Bend, Oregon — December 13, 2025 — The most beloved holiday market in Central Oregon returns for its 17th year! The Locavore Holiday Gift Faire, hosted by Central Oregon Locavore Nonprofit, will take place Saturday, December 13, 2025, at the Unitarian Universalist Fellowship (61980 Skyline Ranch Rd.) from 10 a.m. to 3 p.m., with a special VIP Shopping Hour from 9–10 a.m.

Craft-O! Holiday Bazaar
2025-12-13 09:00 - 2025-12-14 17:00, 2025-12-14 09:00 - 17:00 | The Old Iron Works, 50 SE Scott St., Bend, 97702
Craft-O! is the ultimate destination for locally crafted holiday shopping, hosted by The Workhouse, Gathered Wares, ​Mud Lake Studios, Furnish Hope & Home and Desert Rose Cactus Lounge. Peruse offerings from around 50 talented artisan vendors, and warm up at Cafe Des Chutes with boozy lattes, hot cocoa or a glass ​of wine.

Free Holiday Dog Photo at Mountain Dogs Pet Resort
2025-12-13 10:00 - 14:30 | Mountain Dogs Pet Resort, 1044 SE Paiute Way, Bend, OR, 97702, United States
Mountain Dogs Pet Resort, a newly opened dog daycare and boarding facility in Southeast Bend, is inviting local families to participate in a free holiday photo event featuring their dogs. The event is open to the public, but we are asking families to register in advance at https://bit.ly/MountainDogsHolidayPhotos.
Attendees may choose from two themed backdrops: a traditional photo with Santa or a Hanukkah-themed setting for those who celebrate. Families are welcome to join their dogs in the photos.
The dates for the photo sessions are:
Saturday, 12/6/25 10AM-2:30 PM
Sunday, 12/7/25 10AM-2:30 PM
Saturday, 12/13/25 10AM-2:30 PM

Somewhere That's Green's Magical Markets of Merriment
2025-12-13 10:00 - 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

Healing Reins Holiday Cheer Drive Thru
2025-12-13 14:00 - 16:00 | Healing Reins Equine Assisted Services, 65325 Cline Falls Road, Bend, 97701, United States
Come one, come all for some holiday cheer! Drop off letters to Santa, snap a picture, grab some hot cocoa & say hello to our amazing Healing Herd!

White Truffle and Nebbiolo Tasting at Viaggio
2025-12-13 15:00 - 17:00 | Viaggio Wine Merchant, 210 SW Century Drive, Ste 160, Bend, 97702
Save the date! There are few things more special than the natural kinship of Nebbiolo and white truffles. This will be our third annual celebration of this classic, amazing pairing, featuring a small plates tasting course designed to highlight the aromatic and gastronomic qualities of tartuffi di bianchi (the famed white truffles of Alba, Italy) alongside a selection of show-stopping Nebbiolo. Homemade pasta demonstration included. Save your seats now! Limited to 12 guests. Price TBD by market prices of truffles. Get in touch to reserve and for more details.

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.

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.

Seeds of Intention: Solstice Garland Workshop
2025-12-15 08:00 - 17:00, 2025-12-15 18:00 - 20:00 | 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
