Experience Events
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Events, Events & More Events!
We constantly strive to deliver unique experiences to visitors, vacationers, and locals and hope you'll enjoy the variety of events planned. Our doors are open and ready to welcome all who want to venture out and explore our wide-open spaces. View this Google sheet to download our weekly list of things to do. Check out our Happy Hours, Deals & Specials! *Please note, all dates and events are subject to change.
Event Calendar
Select Dates
Event Categories
October 10, 2026
8:30-11pm
Pepe Osaka's fishtaco and tequila Bar
You asked for it… and we brought it back! Join us at Pepe Osaka’s on Saturday, October 10 at 8:30
October 12, 2026
- October 26, 2026
5-7pm
Big Trout Brewing Company
Join us every Monday for Live Music! Our list of musicians is below, please note this is subject to change
October 14, 2026
4-6:30pm
Headwaters Center
Business Bonanza! A new twist on the classic Business Expo. Discover What’s Local — COME CURIOUS. LEAVE CONNECTED. YOUR COMMUNITY
October 24, 2026
4-6pm
Cooper Creek Square
Wear your favorite costume to trick-or-treat at all the businesses, plus a free photo booth and a DJ Dance Party
November 14, 2026
8am-2pm
Winter Park Resort
Register: In-person only. No registration fee. Check-in at the Derailer Bar registration table starting at 8:00 AM. Collect Cards: Ski
November 26, 2026
9:30-11am
Cooper Creek Square
Lace up your running shoes and start your Thanksgiving morning with some fresh mountain air and festive fun! Join us
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Volunteer Information
Get Involved in Winter Park Events
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