Top 2026 Holiday Events in Central Oregon

The Holiday Season's Best Events in Central Oregon

Your Guide to Holiday Events in Central Oregon

Holidays in Central Oregon bring sparkling lights, festive traditions, and a cozy winter atmosphere. From community parades and craft fairs to mountain events and holiday meals, this season has something for everyone. Here’s a look at what’s happening around Bend, Sunriver, Sisters, and beyond:

Every Thursday

• Winter Nights at the High Desert Museum - During this event, the Museum will remain open until 7:00 pm with seasonal themes, cookie decorating, storytelling, and more! $12.00 per ticket.
• Firesides Music Series – The Suttle Lodge. An opportunity to see amazing acts in an intimate setting. Musicians are hosted nearly every Thursday through April. $12.60 per ticket (includes additional online fees).

Every Weekend

• Hot Cocoa Bar at Lady Bird Cultural Society – Old Mill District (Bend). Featuring a special holiday menu, happy hour drink prices, and delicious treats, this event runs every weekend from 12:00 pm to 4:00 pm through December 27^th.
• Santaland in the Old Mill District - Old Mill District (Bend). SantaLand is a magical holiday experience. Families can enjoy Santa meet-and-greets, and kids can share their holiday wishes before sending their wish lists through the special North Pole Express mailboxes outside SantaLand. No postage stamps are needed! Just include a return address on the envelope so Santa knows where to send a handwritten letter in reply. This event runs December 4-6, December 11-13, and December 18-21. Event begins at 11:00 am and ends at 5:00 pm.

November 14

• Old Fashioned Christmas – Deschutes County Fair & Expo Center (Redmond). Get ready for a variety of gifts, art, crafts, antiques, food, and more! This event runs November 14-15.
• Visions of Sugarplums Bake and Craft Sale Extraordinaire – Sunriver, Oregon. Event begins at 10:00 am and ends at 3:00 pm.

November 18

• Nutcracker! Magical Christmas Ballet – Tower Theatre. Doors open at 6:00 pm and the event begins at 7:00 pm. Prices vary from $55.65-129.25 (includes additional fees).

November 20

• Holiday Food & Gift Festival – Deschutes County Fair & Expo Center (Redmond). Shop hundreds of exhibitors and local artisans featuring a variety of unique and handcrafted gifts. Event runs November 20-22. All-day event.

November 21

• Grand Illumination – Sunriver Resort. This year’s tree-lighting ceremony and fireworks show includes a visit from Santa, live music, train rides, telescope viewings, hot cocoa, and much more! Event begins at 12:00 pm and ends at 7:00 pm.
• Annual Holiday Makers Market – Sunriver Brewing Co. Event starts at 12:00 pm and ends at 5:00 pm.

November 26

• I Like Pie Thanksgiving Run – Riverbend Park. On Thanksgiving morning, bring the entire family down to Riverbend Park anytime between 7:30 am and 9:30 am, to run or walk a festive 1.3-mile, 3.14-mile, or 5.3 Mile loop. Adult (18+) day-of registration fee $55. Youth (2-17yrs) day-of registration fee $35.
• Redmond Turkey Trot – Redmond, Oregon. This is a family-friendly event with courses for all ages! Check-in & day-of registration begins at 8:00 am. Event day registration $40.
• Thanksgiving Buffet – Sunriver Resort Great Hall.
• Lake House Thanksgiving Dinner – Sunriver, Oregon.
• Lodge Kitchen Thanksgiving Dinner – Sunriver, Oregon.
• Suttle Lodge’s Thanksgiving Dinner – Sisters, Oregon.

November 27

• Holiday Village Market – Redmond, Oregon. Featuring unique holiday gifts, delicious treats, and Santa! Event runs November 27-28 from 10:00 am to 4:00 pm.

November 28

• Santa’s Workshop & Craft Bazaar – Crook County Fairgrounds (Prineville). Celebrate the season with 12+ free holiday-themed crafts and kids activities, along with train rides, a visit with Santa, and more! Event starts at 9:00 am and ends at 3:00 pm.
• Hot Cocoa Bar at Lady Bird Cultural Society – Old Mill District (Bend). Featuring a special holiday menu, happy hour drink prices, and delicious treats, this event runs every weekend from 12:00 pm to 4:00 pm through December 27^th.
• The Nutcracker: A Child’s Tale – Tower Theatre. Doors open at 1:00 pm and the event starts at 1:30 pm. Adult tickets vary from $34.50-$58.65 (plus additional Historic Preservation fee). Children (3-11yrs) $24.15 (only includes tiers 2-3; additional Historic Preservation fee not included).
• Sisters Holiday Palooza – Sisters, Oregon. This event kicks off with a holiday parade and follows with holiday activities, including the tree lighting ceremony! Event starts at 3:30 pm and ends at 5:30 pm.
• Redmond Starlight Parade – Downtown Redmond. Event starts at 5:00 pm and ends at 7:00 pm.
• Bend Moonlight Market: Tinsel Town - Midtown Ballroom (Bend). Event runs from November 28-29 and begins at 4:00 pm and ends at 10:00 pm.
• Holiday Makers Market - The Grove. Join this festive holiday shopping experience where you will find local makers, artists, small businesses and unique vendors. This event begins at 11:00 am and ends at 3:00 pm.
• Magical Markets of Merriment – Located at Somewhere That’s Green in Bend. This is one of Bend’s most beloved holiday markets and boasts rotating weekend vendors and a wide selection of curated goods. Don’t forget to grab a delicious cookie from Sandra Claus! This event runs November 28-29 and begins at 10:00 am and ends at 5:00 pm.

December 1

• Jake Shimabukuro: Holidays in Hawaii – Tower Theatre. Doors open at 6:30 pm and the event begins at 7:30 pm. Prices vary from $32-$42, plus additional Historic Preservation fee.

December 3

• Ebenezer Scrooge’s Big Bend Christmas Show! – Cascades Theatrical Company. This event runs December 3- 20. Prices vary from $44-$49.
• Winter Nights - Evergreen Dreams - High Desert Museum. You'll find everything from a scavenger hunt, art projects, tasty treats, storytelling, and more! Event starts at 4:00 pm and ends at 7:00 pm. Tickets are $12.00.

December 4

• Mt. Bachelor Opening Day
• First Friday Art Walk – Old Mill District (Bend). This event will kick off the holiday season with carolers, festive windows, holiday shopping, and a hot cocoa crawl.

December 5

• Festival of Trees – Deschutes County Fair & Expo Center (Redmond). All-day event.
• Downtown Christmas Tree Lighting – Downtown Bend. Event begins at 5:00pm and ends at 7:30 pm (tree will be lit at 6:00 pm).
• Bend Christmas Parade – Downtown Bend. Event begins at 12:00 pm.
• Mistletoe Miler – Join Cascade Relays for a 3-mile fun run & walk along the Deschutes River Trail. Event begins at 9:30 am. Adult registration (18+) $45. Youth registration (2yrs-17yrs) $25.
• Ugly Christmas Sweater 5K – Sisters, Oregon. This is a family-friendly event, and attendees are encouraged to come dressed in their favorite Ugly Christmas Sweater. Kids dash begins at 9:45 am and the 5K begins at 10:00 am. Adult registration (15+) $39. Youth registration (under 15) $30.
• Schilling’s Holiday Makers Market – Located off of the Old Bend Redmond Highway, this event runs December 5-6 from 10:00 am to 4:00 pm.
• The Winter Lantern: Legend of Caerwyn – Tower Theatre. This event runs December 5-6. Doors open at 6:15 pm and the event begins at 7:00 pm. Prices vary from $31-$51, plus additional Historic Preservation fee.

December 6

• Bend Holiday Market – Bend, Oregon. Browse unique gifts and support local businesses! Event begins at 10:00 am and ends at 3:00 pm.

December 8

• Sparkle, Spirits & Snowflakes – Sunriver Resort. Join the resort for a night of delectable food, dancing, fames, and engagement! Event begins at 4:30 pm and ends at 9:00 pm. $130 per ticket.

December 9

• Rock the Holidays with Concert Rock Violinist Aaron Myer – Tower Theatre. Event starts at 7:00 pm. Tickets: $45-$65 + fees; $25 for ages 25 and under.

December 10

• A John Prine Christmas with Jenner Fox Band – Tower Theatre. Doors open at 6:30 pm and the event begins at 7:30 pm. Prices vary from $17-$37, plus additional Historic Preservation fee.
• Winter Nights - Once Upon a Winter - High Desert Museum. You'll find everything from a scavenger hunt, art projects, tasty treats, storytelling, and more! Event starts at 4:00 pm and ends at 7:00 pm. Tickets are $12.00.

December 11

• Broadway in Bend – Tower Theatre. Doors open at 6:00 pm and the event begins at 7:00 pm. General Seating $54, Children (12 & under) $36.75, Premium Seating $123 (includes admission to reception). Prices listed include all fees.
• 18^th Annual Locavore Holiday Gift Faire - Unitarian Church in Bend. This annual market boasts 80+ vendors, handmade goods, artisan food, gifts, and crafts. This beloved community tradition draws in 3,000+ shoppers each season. Get ready for a cozy and festive atmosphere! This event runs December 11 from 4:00 pm to 7:30 pm and December 12 from 9:00 am to 3:00 pm.
• Holiday Lights Paddle Parade – Old Mill District (Bend). Paddlers dress up in costume and decorate their kayaks, canoes, and stand-up paddleboards with colorful lights and holiday gear. The parade kicks off shortly before sunset! Event starts at 4:00 pm and ends at 7:00 pm.

December 12

• Craft-0! Holiday Bazaar – Located in Bend. Get ready for the annual 16^th Craft-0! Bazaar where you will find handmade gifts by local artists, delicious food, and libations. This unique selection of artisan goods will make your holiday season truly special. Event runs December 12-13 from 9:00 am to 5:00 pm (both days). 
• Tinsel and Trees - Located at On Tap in Bend. Join Market House Social for an afternoon of local shopping, family fun, and memorable holiday traditions. Find gifts, pick out a Christmas tree at the on-site tree lot, and catch a photo with Santa! Event begins at 12:00 pm and ends at 6:00 pm.

December 14

• The Nutcracker: Symphony of Lights – Tower Theatre. Doors open at 6:00 pm and the event begins at 7:00 pm. Prices vary from $52.50-$91.50, plus additional Historic Preservation fee.

December 16

• Santa Pajama Jam – Bend, Oregon. Kids come dressed in pajamas, visit Santa, make ornaments, and more! Event begins at 1:30 pm and ends at 3:00 pm. $28 per child's pass (2 adults included per pass, additional must pay).

December 17

• Winter Nights - Moon Light Bright - High Desert Museum. You'll find everything from a scavenger hunt, art projects, tasty treats, storytelling, and more! Event starts at 4:00 pm and ends at 7:00 pm. Tickets are $12.00.

December 18

• Swingin’ Tower Christmas – Tower Theatre. This is a family-friendly holiday spectacular with lively music and heartwarming stories. Doors open at 6:30 pm and the event begins at 7:00 pm. Prices vary from $32-$52, plus additional Historic Preservation fee.

December 22

• National Lampoons CHRISTMAS VACATION – Tower Theatre. Doors open at 6:00 pm and the movie begins at 7:00 pm. $12 per ticket, plus additional Historic Preservation fee.

December 31

• New Year’s Eve Bash – McMenamins Old St. Francis School. Get ready for a night of dancing, live music, and a midnight toast to the New Year! Doors open at 8:00 pm and the event begins at 9:00pm. $35 per ticket purchased in advance. $40 per ticket for day of event.
• New Years Eve with Kota Dosa – The Belfrey (Sisters). Event begins at 8:00 pm. 
• New Year’s Eve Bonfire on the Snow – Hosted by Wanderlust Tours. Event begins at 9:00 pm and ends at 1:15 am. $170 per ticket (children 12+ are welcome).

Book your vacation rental and enjoy all the festive December events in Central Oregon for an unforgettable stay!