Stay Vara Events
Upcoming Events in Winter Park
From live music and mountain biking to food festivals and community celebrations, Winter Park offers events throughout the season for visitors of all ages.
AUGUST 20 & 27, 2026
High-Note Thursday
Spend a summer evening enjoying free live music at the Rendezvous Event Center in downtown Winter Park.
Time: 6:00 PM - 8:00 PM
AUGUST 21, 28 & SEPTEMBER 4, 2026
Music on the Square
Enjoy live blues, Americana, jazz and country music surrounded by the shops and restaurants of Cooper Creek Square.
Time: 6:00 PM - 8:00 PM
AUGUST 22, 2026
Tacos + Margs in the Mountains
Head to Winter Park Resort for an afternoon celebrating tacos, margaritas and mountain views during this all-ages summer event.
Time: 11:00 AM - 4:00 PM
AUGUST 22, 2026
Community Fest Fundraiser
Celebrate the end of summer with family-friendly activities and community fun at the Rendezvous Event Center.
Time: 11:00 AM - 3:00 PM
AUGUST 22, 2026
Tipperary Classic
One of Winter Park's established mountain bike races returns to Winter Park Resort as part of the Winter Park Classics XC Series.
AUGUST 27, 2026
High-Note Market
Browse local vendors and enjoy an evening in downtown Winter Park at the Rendezvous Event Center.
Time: 5:30 PM - 8:00 PM
SEPTEMBER 11 - 12, 2026
Plein Air @ Altitude
Celebrate mountain art and creativity during this two-day event at the Rendezvous Event Center in Winter Park.
SEPTEMBER 18 - 20, 2026
Oktoberfest Hop Crawler
Celebrate Oktoberfest throughout Winter Park and Fraser with a weekend centered around local breweries, gathering spots and mountain-town festivities.
