Aspen & Roaring Fork Valley Events - Holiday Season 2023

Stephanie Kroll

As the snow blankets the charming town of Aspen, Colorado, the holiday season ushers in a flurry of festivities and joy. From enchanting markets to exhilarating races, Aspen transforms into a winter wonderland, inviting both locals and visitors to revel in the magic of the season. Here's your guide to the must-attend events during the holiday season in Aspen.

1. 12 Days of Aspen: A Winter Wonderland Unleashed Dates: Dec. 20 - 31 Downtown Aspen comes alive with the 12 Days of Aspen, a celebration spanning from December 20 to 31. The town turns into a winter wonderland, offering everything from ice skating and delectable holiday treats to melodious carolers. The 12-day extravaganza concludes with a breathtaking fireworks display over the iconic Aspen Mountain. For more information, visit

2. Wintersköl: Aspen's Toast to Winter Dates: Jan. 11 - 14 Wintersköl, Aspen's "toast to winter," spans four days of vibrant activities from January 11 to 14. The event includes Anderson Ranch Arts Center’s Kidsculpt, a torchlight descent on Aspen Mountain, the Canine Fashion Show, fireworks, and more. Immerse yourself in the magic of winter with this annual celebration. Learn more at

3. Aspen Holiday Market: A Winter Debut Date: Ongoing Experience the winter charm of Aspen at the Aspen Holiday Market, a festive outdoor market in downtown Aspen. Local artisans and crafters showcase unique holiday gifts, decorations, and homemade treats, creating a magical shopping experience. Discover more at

4. Winter Jazz Fest at The Little Nell: Rhythmic Bliss in the Mountains Indulge in a weekend of smooth jazz performances by renowned artists at The Little Nell. The Winter Jazz Fest offers a cozy and sophisticated atmosphere in one of Aspen’s most iconic hotels. For more jazz-filled details, head to

5. Aspen Santa Run: Jogging Through the Winter Wonderland The Aspen Santa Run combines fitness and festive spirit as participants don Santa Claus attire for a charity run through the scenic streets of Aspen. The event concludes with a community holiday feast. Learn more and join the festive run at

6. Summit for Life: Racing Uphill for a Cause Date: Ongoing; Details for 2023 Summit for Life Join the Chris Klug Foundation for the 2023 Summit for Life, a nighttime uphill race up Aspen Mountain. This event, a fundraiser for organ, eye, and tissue donation awareness, invites participants to climb 3,267 vertical feet to the summit. Celebrate at the top with dinner, live music, and awards. For registration and details, visit

7. Tree Lighting in Willits: Illuminating the Holiday Spirit Date: December 1, 2023 Triangle Park in Willits comes alive on December 1st with a magical Tree Lighting ceremony at 4 PM. Join the community in embracing the holiday spirit with festive lights and seasonal cheer.

8. Old Thompson Holiday Barn Market: A Festive Shopping Affair Date: December 3, 2023 Get into the holiday shopping spirit at the Old Thompson Holiday Barn Market in Carbondale on December 3rd. With over 30 local vendors, holiday photos with the High Country Photo Bus, and fresh wreaths and flowers, this free event promises a delightful afternoon of festive indulgence from 1 PM to 5 PM.

9. Polar Express at Wheeler Opera House Date: December 10th Aspen Film and the Wheeler Opera House are teaming up to present a special screening of the modern holiday classic, "The Polar Express." Admission to this heartwarming film is free, but in the spirit of giving, attendees are encouraged to bring either a food or toy donation for admittance. The Roaring Fork Youth Orchestra will set the festive tone with a prelude of holiday tunes, creating a joyous atmosphere. Don't miss the chance to immerse yourself in the magic of the Polar Express. The event starts at 4 PM, and Paradise Bakery will be providing free refreshments.

10. Dance Aspen: A Snow Soiree Date: December 23, 2023 | 1:00 PM Step into a world of grace and elegance with Dance Aspen's holiday-themed show. Set to dazzle for approximately thirty minutes on the main stage of the Wheeler Opera House, the performance features the Dance Aspen company in vibrant, festive costumes. After the show, patrons can enjoy post-show cocoa and cookies in the beautifully decorated Wheeler lobby. This all-ages, all-welcome performance invites families to share in the holiday spirit, creating lasting memories.

11. Redstone Inn Annual Christmas Holiday Tea Dates: December 21st and December 28th | 11:30 AM - 3 PM For a touch of classic elegance, indulge in the Redstone Inn's Annual Christmas Holiday Tea. With two opportunities on December 21st and December 28th, this highly anticipated event offers a refined experience. Reservations are required due to limited space, so be sure to call 970-963-2526 to secure your spot. Delight in a fine selection of loose-leaf tea, accompanied by finger sandwiches, a holiday salad, homemade scones with clotted cream and jam, and an array of sweet desserts. Gluten-free options will also be available for a delightful afternoon in the charming surroundings of Redstone Inn.

As the crisp mountain air fills with the sounds of joy and the twinkling lights of the season adorn the streets, Aspen welcomes you to join in the merriment of the holiday season. Explore, indulge, and create cherished memories in this winter wonderland.

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