GarageCherries
Winter Garden, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Winter Garden, Florida.
20 upcoming events in Winter Garden
Browse cars for sale in Florida →Get this weekend's car shows near you, every Thursday
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Upcoming Events in Winter Garden
Oct
15
Flamingos & Fuel Cruise Night
Oct 15, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
24
Cars and Coffee Winter Garden
Oct 24, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
1
Horizon West Cars & Coffee
Nov 1, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
20
Flamingos & Fuel Cruise Night
Nov 20, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
28
Cars and Coffee Winter Garden
Nov 28, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
6
Horizon West Cars & Coffee
Dec 6, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
17
Flamingos & Fuel Cruise Night
Dec 17, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
26
Cars and Coffee Winter Garden
Dec 26, 2026 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
22
Flamingos & Fuel Cruise Night
Jan 22, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
23
Cars and Coffee Winter Garden
Jan 23, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
7
Horizon West Cars & Coffee
Feb 7, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
19
Flamingos & Fuel Cruise Night
Feb 19, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
27
Cars and Coffee Winter Garden
Feb 27, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
7
Horizon West Cars & Coffee
Mar 7, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
18
Flamingos & Fuel Cruise Night
Mar 18, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Mar
27
Cars and Coffee Winter Garden
Mar 27, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Horizon West Cars & Coffee
Apr 4, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
15
Flamingos & Fuel Cruise Night
Apr 15, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
May
20
Flamingos & Fuel Cruise Night
May 20, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
6
Horizon West Cars & Coffee
Jun 6, 2027 · Winter Garden, FL
Regular cars and coffee / cruise-in gathering in Winter Garden, 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.