Hole for the Holidays: Jackson Holiday Events
Dropping by Jackson Hole for the holiday season? ’Tis the season for cocoa, crafts, shopping sprees, and more winter cheer than you can shake a sleigh at. (We only get one “ ‘tis the season” per blog post, and we just used it. Hold us to it, please.) So here’s our specially curated list of some of the best holiday happenings on town:
Winter Wings and Holiday Cheer
Date: Tuesday, December 2, 2025, 4–6 p.m.
Location: Teton Raptor Center
Price: Free
Sip, shop, and mingle with birds whose beady eyes are probably judging your scarf. The Nature Shop will be stocked with avian-inspired gifts, the Learning Lab will be buzzing with crafts, and from 4:30–5:30 p.m., an Avian Ambassador will grace guests with its presence. Light refreshments provided. Talons optional.
Holiday Bazaar
Dates: December 5–6, 2025, 10 a.m.–4:30 p.m.
Location: Jackson Hole Conference Center, 920 W Broadway
Price: $6 adults; free for ages 12 and under
The Art Association’s annual spree of ceramics, textiles, jewelry, woodwork, photography, and other handcrafted treasures. Your chance to shop local, meet makers, and pretend you were planning thoughtful gifts like this all along. Proceeds support the Art Association’s year-round programs.
Shop Local Holiday Weekend
Dates: Weekends throughout December
Location: Jackson Town Square
Price: Free to wander; potential financial damage varies
Free hot cocoa and homemade cookies from Jedediah’s (1–4 p.m., Sat & Sun). Local gift guides, Winter Windfall promos, and—oh, yeah!—the chance to enter for $5,000 worth of shopping sprees.
Christmas at the Playhouse
Dates: December 10, 2025 – January 3, 2026
Time: 5:15–8:45 p.m.
Location: Jackson Hole Playhouse, 145 W Deloney Ave
Price: $125/adult; $110/teen; $90/child
A cozy dinner-theater night featuring festive tunes, hearty entrées, and a talented cast. Drinks beyond the soft variety cost extra, but the cheer is baked in.
Santa on the Square
Dates: December 13–24, 2025 (excluding Dec 15–16), 5–7 p.m.
Location: Town Square, Jackson
Price: Free
Ten nights of classic holiday magic under the famous antler arches. Kids can meet Santa, snag a cookie from Jedediah’s, and sip hot cocoa. Parents can capture the ultimate holiday photo. Santa commits to abstain from promising that your kids will get an Xbox for Christmas.
Thrift & Shift Holiday Market
Date: Saturday, December 13, 2025, 10 a.m.–5 p.m.
Location: The Virginian Lodge, 750 W Broadway
Price: Free
Over 40 vendors selling vintage finds, handmade goods, and sustainable treasures. DJ Moody Saison brings the holiday soundtrack while Billy’s Burgers provides fuel.
Teton Habitat Gingerbread House Showcase
Date: Tuesday, December 16, 2025, 9 a.m.–8 p.m.
Location: Goldpiece Room, The Wort Hotel
Price: Free; raffle tickets available for voting
Fifth graders are tasked with building “affordable” homes from gingerbread, and frankly, given real estate prices, they might be onto something. Tour the sugary neighborhood, vote for your favorite, and support Habitat for Humanity’s local housing programs.
Gingerbread House & Cookie Decorating
Date: December 22, 2025, 4–7 p.m.
Location: Silver Dollar Bar & Grill, 50 N Glenwood
Price: $34–$95 depending on how ambitious your sugar engineering gets
Your turn. Cookie decorating includes a dozen cookies, icing, sprinkles, and enough candy to ensure someone doesn’t sleep tonight. Gingerbread house decorating comes with all the materials for your edible architectural triumph or collapse. A perfect event for families, date nights, or anyone who wants to nurture their inner Frank Lloyd Wright.
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Which Jackson Hole holiday events will you be attending? Come tell us all about it when you check for a stay at Flat Creek Inn.
Photo courtesy Jackson Hole Chamber of Commerce, to whom we're also indebted for our calendar.
Ryan Kunz is a copywriter and freelance writer who writes on a variety of topics, including media, the outdoors, and whatever else strikes his fancy. If anyone wants to get him a Christmas present, some tickets to the Jackson Hole Playhouse would be really fun.
