GarageCherries
Holiday, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Holiday, Florida.
25 upcoming events in Holiday
Browse cars for sale in Florida →Get this weekend's car shows near you, every Thursday
Just your email and ZIP — shows within 50 miles, no account needed.
Upcoming Events in Holiday
May
22
The 50’s Diner Cruise-In
May 22, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
5
The 50’s Diner Cruise-In
Jun 5, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
5
50’s Diner Weekly Cruise-In Car Show
Jun 5, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
12
The 50’s Diner Cruise-In
Jun 12, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
12
50’s Diner Weekly Cruise-In Car Show
Jun 12, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Car Shows in Nearby Cities
Cars for sale in Florida
2023 Ford Mustang Mach 1
1932 Ford Roadster
1985 Buick Riviera Coupe
1932 Ford Hi-Boy
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.