GarageCherries
Holiday, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Holiday, Florida.
25 upcoming events in Holiday
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This Weekend in Holiday · Oct 16–Oct 18
Oct
17
The 50’s Diner on US 19 Cruise In
Oct 17, 2026 · Holiday, FL
Car show in Holiday, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
50’s Diner Weekly Cruise-In Car Show
Oct 17, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Holiday
Oct
17
The 50’s Diner on US 19 Cruise In
Oct 17, 2026 · Holiday, FL
Car show in Holiday, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
50’s Diner Weekly Cruise-In Car Show
Oct 17, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
24
The 50’s Diner Cruise-In
Oct 24, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
7
Veterans First Saturday Car Show and Dinner
Nov 7, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
5
Veterans First Saturday Car Show and Dinner
Dec 5, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
26
The 50’s Diner Cruise-In
Dec 26, 2026 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
2
Veterans First Saturday Car Show and Dinner
Jan 2, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
9
The 50’s Diner Cruise-In
Jan 9, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
9
50’s Diner Weekly Cruise-In Car Show
Jan 9, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
16
50’s Diner Weekly Cruise-In Car Show
Jan 16, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
6
Veterans First Saturday Car Show and Dinner
Feb 6, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
13
The 50’s Diner Cruise-In
Feb 13, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
13
50’s Diner Weekly Cruise-In Car Show
Feb 13, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
20
The 50’s Diner Cruise-In
Feb 20, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
6
Veterans First Saturday Car Show and Dinner
Mar 6, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
27
50’s Diner Weekly Cruise-In Car Show
Mar 27, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
27
The 50’s Diner Cruise-In
Mar 27, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
3
Veterans First Saturday Car Show and Dinner
Apr 3, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
17
50’s Diner Weekly Cruise-In Car Show
Apr 17, 2027 · Holiday, FL
Regular cars and coffee / cruise-in gathering in Holiday, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
17
The 50’s Diner Cruise-In
Apr 17, 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.