Craft Fairs & Holiday Markets in Douglas County

The marquee fall show is the 34th Annual Castle Rock Craft Show Extraordinaire at the Douglas County Fairgrounds and Event Center, Saturday, November 7, 2026, 9 a.m. to 4 p.m., free admission. It is hosted by the Castle Rock Senior Activity Center, with proceeds benefiting its programs for older adults in the area. Earlier in the season, the HRCA Fall Craft Fair at Eastridge Rec Center in Highlands Ranch (September) and Chaparral High School’s Autumn Artisan Market in Parker (late October) run the first waves of fall craft shopping.

The biggest is the Festival Park Starlight Market in downtown Castle Rock, Friday, December 4 (3 to 8 p.m.) and Saturday, December 5 (11 a.m. to 7 p.m.), with 40-plus vendors, food trucks, hot cocoa and a 40-foot decorated tree. The Castle Rock Christmas Market at Plum Creek Church runs Saturday, December 5, 9 a.m. to noon (dozens of local artisans; over 500 neighbors shopped last year), and 105 West Brewing’s 105 Christmas Market takes over the Castle Rock taproom the weekend of December 12 and 13. Most are free to attend.

Saturday, November 7, 2026, 9 a.m. to 4 p.m., at the Douglas County Fairgrounds and Event Center (500 Fairgrounds Rd). It’s free to shop, the 34th year for the show, and benefits the Castle Rock Senior Activity Center’s programs for older adults.

Parker’s Mountain Pine Woman’s Club Annual Yuletide Bazaar at the Parker Fieldhouse is confirmed for Saturday, November 14, 2026, 9 a.m. to 4 p.m., with over 100 artisans and vendors, door prizes, and a visit from Santa and Mrs. Claus. The same Saturday, Highlands Ranch has HRCA’s Holiday Gift Fair at Eastridge Recreation Center (9 a.m. to 5 p.m.), and Grace Chapel in Castle Rock runs its own Christmas Market Fair (10 a.m. to 5 p.m.). The Holly Jolly Christmas Boutique at The Grange in The Meadows (Castle Rock) has returned most years in mid-November; we add the 2026 date here once it posts.

The Castle Rock Chamber sells a commemorative Starlighting ornament each year, a gold-plated collector’s piece with a different historic Castle Rock site on it, through its Starlighting ornament page. They sell at the Starlighting celebration and the Chamber office, and past-year ornaments are sometimes still available at the office.

The Downtown Castle Rock Sip & Stroll is the big shop-local night: a free passport crawl on Thursday, December 3, 2026, 5 to 8 p.m., where downtown shops stay open late with festive sips, deals and gift-card giveaways, plus horse and carriage rides. Small Business Saturday (the Saturday after Thanksgiving) and the holiday events at the Outlets at Castle Rock round out the shop-local calendar.