GarageCherries
Leonardtown, MD Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Leonardtown, Maryland.
9 upcoming events in Leonardtown
Browse cars for sale in Maryland →Get this weekend's car shows near you, every Thursday
Just your email and ZIP — shows within 50 miles, no account needed.
This Weekend in Leonardtown · Oct 16–Oct 18
Oct
18
Town Market Coffee & Cars
Oct 18, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Cars & Coffee Car Show
Oct 18, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Leonardtown
Oct
18
Town Market Coffee & Cars
Oct 18, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Cars & Coffee Car Show
Oct 18, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
29
Town Market Coffee & Cars
Nov 29, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
13
Town Market Coffee & Cars
Dec 13, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Town Market Coffee & Cars
Dec 27, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Town Market Coffee & Cars
Jan 10, 2027 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Town Market Coffee & Cars
Apr 4, 2027 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
18
Town Market Coffee & Cars
Apr 18, 2027 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Jun
13
Town Market Coffee & Cars
Jun 13, 2027 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Car Shows in Nearby Cities
Cars for sale near Maryland
1969 Ford Mustang Mach 1 Cobra Jet
1967 Ford Mustang Sport Sprint Coupe
1973 Volkswagen Thing
1965 Chevrolet Impala SS
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.