As summer unfolds in Winter Park, Colorado, the community is buzzing with a variety of events that cater to art enthusiasts, music lovers, and festival-goers alike. Here’s a look at some upcoming happenings you won’t want to miss.
Winter Park Alpine ArtAffair
Dates: July 11–12, 2026
Location: Downtown Winter Park, along Highway 40 near the Post Office
The Alpine ArtAffair is a two-day art fair showcasing crafts and artwork by local and regional artists. Attendees can explore a diverse range of art forms, including jewelry, photography, metalwork, pottery, painting, and glasswork. The event also features food vendors, children’s activities, and live music, making it a perfect outing for the whole family. Admission is free, and the fair runs from 9:00 AM to 5:00 PM each day.
TheBigWonderful Beer Fest & Bluegrass
Date: July 11, 2026
Time: 12:00 PM – 6:00 PM
Location: The Village at Winter Park Resort
This festival offers a full day of live bluegrass concerts, unlimited beer samples from Colorado breweries, and a craft market featuring unique finds. The event schedule includes performances by High Lonesome, Brandywine & The Mighty Fines, Wrecklunds, Alex Thoele Band, and That Damn Sasquatch. Tickets are required for the beer fest portion, while access to the craft vendor village and live music is free. Additionally, event ticket holders can enjoy a 50% discount on scenic gondola rides.
43rd Annual Winter Park Jazz Festival
Dates: July 18–19, 2026
Location: Rendezvous Event Center, 78821 US Hwy 40, Winter Park, CO 80482
The Winter Park Jazz Festival returns for its 43rd year, featuring a stellar lineup of jazz talent. Saturday’s performances include Patti LaBelle, Damien Escobar, Najee, Purple Magic featuring Marcus Anderson, BK Jackson, Adrian Crutchfield, and Gregory Goodloe. Sunday’s lineup boasts Brian Culbertson, After 7, Kim and Kayla Waters, JJ Sansaverino with Lin Rountree and Art Sherrod Jr., and Nelson Rangell. Gates open at 10:00 AM each day, with early entry and ADA access available at specified times. Tickets are available for purchase, and attendees are encouraged to review event and venue rules prior to arrival.
These events highlight the vibrant cultural scene in Winter Park and offer residents and visitors alike the opportunity to engage with the community through art, music, and local traditions. Be sure to mark your calendars and enjoy all that our town has to offer this summer.