GarageCherries
Middleburg, FL Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Middleburg, Florida.
16 upcoming events in Middleburg
Browse cars for sale in Florida →Get this weekend's car shows near you, every Thursday
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This Weekend in Middleburg · Oct 16–Oct 18
Oct
18
PJ’s Cars & Coffee
Oct 18, 2026 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Middleburg
Oct
14
Whiskey & Wings Cruise In
Oct 14, 2026 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Oct
18
PJ’s Cars & Coffee
Oct 18, 2026 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
16
Whiskey & Wings Cruise In
Dec 16, 2026 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Dec
27
PJ’s Cars & Coffee
Dec 27, 2026 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
3
PJ’s Cars & Coffee
Jan 3, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
6
Whiskey & Wings Cruise In
Jan 6, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
10
PJ’s Cars & Coffee
Jan 10, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
17
PJ’s Cars & Coffee
Jan 17, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jan
20
Whiskey & Wings Cruise In
Jan 20, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
7
PJ’s Cars & Coffee
Feb 7, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
10
Whiskey & Wings Cruise In
Feb 10, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
17
Whiskey & Wings Cruise In
Feb 17, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Feb
28
PJ’s Cars & Coffee
Feb 28, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Apr
18
PJ’s Cars & Coffee
Apr 18, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
9
Whiskey & Wings Cruise In
Jun 9, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, Florida, drawing classic cars, hot rods, and collector vehicles.
Jun
13
PJ’s Cars & Coffee
Jun 13, 2027 · Middleburg, FL
Regular cars and coffee / cruise-in gathering in Middleburg, 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.