GarageCherries
Kissimmee, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Kissimmee, Florida.
140 upcoming events in Kissimmee
Browse cars for sale in Florida →Get this weekend's car shows near you, every Thursday
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Upcoming Events in Kissimmee
Jan
14
Old Town Bike Night
Jan 14, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
15
Promenade Racing Car & Truck Show
Jan 15, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Jan
15
Fired Up Fridays
Jan 15, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
15
Friday Muscle Car Show & Cruise
Jan 15, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
15
Old Town Bike Night
Jan 15, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
16
Show Car Saturday Nights
Jan 16, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
16
Saturday Night Old Town Classic Car Show
Jan 16, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
16
Saturday Classic Car Show & Cruise
Jan 16, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
20
Old Town Kissimmee Car Show
Jan 20, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
22
Old Town – Friday Night Muscle Car Show & Cruise
Jan 22, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
24
Old Town Exotic Cars & Coffee
Jan 24, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
31
Import Car Show
Jan 31, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Feb
2
Forsaken Cars & Coffee Night Edition
Feb 2, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
3
Weekly Wednesdayz
Feb 3, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
5
Friday Muscle Car Show & Cruise
Feb 5, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
5
Promenade Racing Car & Truck Show
Feb 5, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Feb
6
Saturday Classic Car Show & Cruise
Feb 6, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
10
Old Town Kissimmee Car Show
Feb 10, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
12
Old Town – Friday Night Muscle Car Show & Cruise
Feb 12, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
12
Fired Up Fridays
Feb 12, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, 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.