GarageCherries
Leesburg, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Leesburg, Florida.
28 upcoming events in Leesburg
Browse cars for sale in Florida →Get this weekend's car shows near you, every Thursday
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This Weekend in Leesburg · Oct 16–Oct 18
Oct
17
Shifters and Shakes Cruise In
Oct 17, 2026 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Leesburg
Oct
15
Cool Cars (& Trucks) Under the Stars
Oct 15, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Oct
17
Shifters and Shakes Cruise In
Oct 17, 2026 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
22
Downtown Leesburg Third Thursdays Car Show
Oct 22, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Nov
14
Leesburg Classic Car Show
Nov 14, 2026 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Nov
19
Cool Cars (& Trucks) Under the Stars
Nov 19, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Nov
26
Downtown Leesburg Third Thursdays Car Show
Nov 26, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Dec
12
Leesburg Classic Car Show
Dec 12, 2026 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
17
Cool Cars Under the Stars
Dec 17, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Dec
18
Shifters and Shakes Cruise In
Dec 18, 2026 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
24
Downtown Leesburg Third Thursdays Car Show
Dec 24, 2026 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Jan
8
Shifters and Shakes Cruise In
Jan 8, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Leesburg Classic Car Show
Jan 9, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
15
Shifters and Shakes Cruise In
Jan 15, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
28
Downtown Leesburg Third Thursdays Car Show
Jan 28, 2027 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Feb
12
Shifters and Shakes Cruise In
Feb 12, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
13
Leesburg Classic Car Show
Feb 13, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
18
Cool Cars Under the Stars
Feb 18, 2027 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Feb
19
Shifters and Shakes Cruise In
Feb 19, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
25
Downtown Leesburg Third Thursdays Car Show
Feb 25, 2027 · Leesburg, FL
Car show in Leesburg, Florida, featuring classic, custom, and collector vehicles on display.
Mar
13
Leesburg Classic Car Show
Mar 13, 2027 · Leesburg, FL
Regular cars and coffee / cruise-in gathering in Leesburg, 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.