Winter Garden Live Music Events

WINTER GARDEN CELEBRATES AMERICA 250

Winter Garden Downtown Historic District 3 Jul 2026

Dead Radio - Winter Garden 4th of July Festival

Newton Park 4 Jul 2026

Join us in downtown Winter Garden for the 4th of July!

Winter Garden Downtown Historic District 4 Jul 2026

Too Hip to be Square - 1986 All Over Again!

146 W Plant St Suite 210, Winter Garden, FL, United States, Florida 34787 1 Jul 2026

Boxer Engine FL present Park and chill

14180 W Colonial Dr, Winter Garden, FL 34787 27 Jun 2026

Saturday: Patriotism on Plant: A Musical Journey Celebrating America’s 250th

Garden Theatre 25 Jul 2026

Sunday: Patriotism on Plant: A Musical Journey Celebrating America's 250th

Garden Theatre 26 Jul 2026

Learn about River Cruising and win BIG!

The Attic Door 8 Jul 2026

Monster of the Week — Live Improv TTRPG

Lucky Straws Boba Tea of Winter Garden 27 Jun 2026