Featured Summer Events
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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.
Summer Events
Select Dates
Event Categories
September 19, 2026
1-6pm
Rendezvous Event Center
The community is invited to Winter Park’s Annual Fall Festival on Saturday, September 19th at the Rendezvous Event Center and
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
June 25, 2027
- June 27, 2027
4-10pm
Rendezvous Event Center
Get ready, June 25-28, 2027, for the ultimate blues experience at the 25th Annual Blues from the Top Music Festival