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
Dec
26
Show Car Saturday Nights
Dec 26, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Old Town Exotic Cars & Coffee
Dec 27, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Import Car Show
Dec 27, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Dec
29
Forsaken Cars & Coffee Night Edition
Dec 29, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
30
Weekly Wednesdayz
Dec 30, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
1
Promenade Racing Car & Truck Show
Jan 1, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Jan
1
Friday Muscle Car Show & Cruise
Jan 1, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
2
Saturday Classic Car Show & Cruise
Jan 2, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
5
–Jan 17
Mecum Kissimmee 2027
Jan 5 – Jan 17, 2027 · Kissimmee, FL
Mecum Auctions' Kissimmee collector car auction at Osceola Heritage Park, with about 4,500 vehicles on the block over thirteen days.
Jan
6
Old Town Kissimmee Car Show
Jan 6, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
8
Promenade Racing Car & Truck Show
Jan 8, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Jan
8
Fired Up Fridays
Jan 8, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
8
Old Town – Friday Night Muscle Car Show & Cruise
Jan 8, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Saturday Night Old Town Classic Car Show
Jan 9, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Saturday Classic Car Show & Cruise
Jan 9, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
10
4Saken Weekly #1 Park & Chill Sundaze
Jan 10, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Jan
10
Promenade at Sunset Walk Car & Truck Show
Jan 10, 2027 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Jan
10
he Promenade Car & Truck Show
Jan 10, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
12
Forsaken Cars & Coffee Night Edition
Jan 12, 2027 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
13
Weekly Wednesdayz
Jan 13, 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.