Featured Events
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Ready for a good time?
Our doors are open and ready to welcome all who want to venture out and explore our wide-open spaces. Below is the current schedule for the season and we'll be adding more! As always, all events are subject to change. We constantly strive to deliver unique experiences to visitors, vacationers, and locals and hope you'll enjoy the variety of events planned. Before traveling, be sure to check out Updates & Alerts.
Check Out Our Featured Events
Select Dates
Event Categories
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 17, 2026
3-8pm
START - Vicious Cycle
It’s almost time to celebrate 30 years of HTA! Join us Saturday, October 17 for the Annual Bike Pub Crawl
December 5, 2026
3:30-5:30pm
Winter Park Resort
The holidays begin now! Kick off the season with a day on the slopes, holiday music, cookies and hot chocolate
December 12, 2026
3:30-5:30pm
Winter Park Resort
Before the sun sets, enjoy festive holiday music, visits with Santa, seasonal entertainment, as well as holiday-themed food and drinks
December 19, 2026
3:30-6pm
Winter Park Resort
Before the sun sets, enjoy festive holiday music, visits with Santa, seasonal entertainment, as well as holiday-themed food and drinks
December 24, 2026
5:30-6:30pm
Winter Park Resort
Our iconic holiday celebration is back, and you’re invited! At 5:30pm, cozy up with a cup of cocoa around the
Winter Park Savings Pass
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