GarageCherries
Kissimmee, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Kissimmee, Florida.
140 upcoming events in Kissimmee
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This Weekend in Kissimmee · Oct 16–Oct 18
Oct
16
Promenade Racing Fridays Car & Truck Show
Oct 16, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
16
Fired Up Fridays
Oct 16, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Friday Muscle Car Show & Cruise
Oct 16, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Old Town Muscle Car Show & Cruise
Oct 16, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
The Promenade Show Car Saturday Nights
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Special Olympics Inclusion Car Show
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Show Car Saturday Nights
Oct 17, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
17
Old Town Classic Car Show
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Saturday Night Old Town Classic Car Show
Oct 17, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Kissimmee
Oct
14
Forsaken Cars & Coffee Night Edition
Oct 14, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
14
Old Town Kissimmee Car Show
Oct 14, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
15
Weekly Wednesdayz
Oct 15, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Promenade Racing Fridays Car & Truck Show
Oct 16, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
16
Fired Up Fridays
Oct 16, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Friday Muscle Car Show & Cruise
Oct 16, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Old Town Muscle Car Show & Cruise
Oct 16, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
The Promenade Show Car Saturday Nights
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Special Olympics Inclusion Car Show
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Show Car Saturday Nights
Oct 17, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
17
Old Town Classic Car Show
Oct 17, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Saturday Night Old Town Classic Car Show
Oct 17, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
21
Forsaken Cars & Coffee Night Edition
Oct 21, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
23
Old Town – Friday Night Muscle Car Show & Cruise
Oct 23, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
25
Old Town Exotic Cars & Coffee
Oct 25, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
25
Import Car Show
Oct 25, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Nov
8
he Promenade Car & Truck Show
Nov 8, 2026 · Kissimmee, FL
Regular cars and coffee / cruise-in gathering in Kissimmee, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
8
Second Sunday Car & Truck Show
Nov 8, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Nov
8
Promenade at Sunset Walk Car & Truck Show
Nov 8, 2026 · Kissimmee, FL
Car show in Kissimmee, Florida, featuring classic, custom, and collector vehicles on display.
Nov
13
Friday Night Muscle Car Show & Cruise
Nov 13, 2026 · 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.