GarageCherries
Maryland Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Maryland for 2026.
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Past Events
Sep
20
Cars & Coffee Waldorf (St. Charles Towne Center)
Sep 20, 2026 · Waldorf, MD
Regular cars and coffee / cruise-in gathering in Waldorf, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Church of The Holy Donut
Sep 20, 2026 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Sep
20
Maryland OBS Chevy Truck Fest
Sep 20, 2026 · Hancock, MD
Car show in Hancock, MD, featuring classic, custom, and collector vehicles on display.
Sep
20
Cars & Coffee Car Show
Sep 20, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Annapolis Cars & Coffee
Sep 20, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Cars & Coffee @ Dunkin Donuts
Sep 20, 2026 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Town Market Coffee & Cars
Sep 20, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Salisbury Pit & Pub Weekly Cruise In
Sep 20, 2026 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Cars and Coffee at the Coffee Beanery Ocean City
Sep 20, 2026 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
19
Hunt Valley Horsepower
Sep 19, 2026 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Sep
19
Top Flight Corvette Club All Car Show
Sep 19, 2026 · Fort Washington, MD
Car show in Fort Washington, MD, featuring classic, custom, and collector vehicles on display.
Sep
19
Three Brothers Italian Restaurant Columbia Cruise Night
Sep 19, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
19
Benedictine's Chrome City Fundraiser
Sep 19, 2026 · Ridgely, MD
Car show in Ridgely, MD, featuring classic, custom, and collector vehicles on display.
Sep
19
Resurrected Car Show
Sep 19, 2026 · 10 AM – 4 PM · Rising Sun, MD
The Resurrected Car Show takes place at The Ballfield, 47 Half Mile Turn in Rising Sun. The show runs from 10 AM to 4 PM and welcomes automotive enthusiasts for a community vehicle showcase.
Sep
19
Poolesville Day Car Show
Sep 19, 2026 · Poolesville, MD
Car show in Poolesville, MD, featuring classic, custom, and collector vehicles on display.
Sep
19
The Damascus Cars and Coffee
Sep 19, 2026 · Damascus, MD
Regular cars and coffee / cruise-in gathering in Damascus, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
19
Lost 50’s Custom Car Club Of Maryland Cruise-Ins
Sep 19, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
19
2nd Annual Taggin’N Baggin For A Cause
Sep 19, 2026 · Avenue, MD
Car show in Avenue, MD, featuring classic, custom, and collector vehicles on display.
Sep
19
Drive each other's cars: Test Drive
Sep 19, 2026 · Gaithersburg, MD
Regular cars and coffee / cruise-in gathering in Gaithersburg, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
19
Top Flight All Car Show
Sep 19, 2026 · 8 AM – 3 PM · Fort Washington, MD
Top Flight Corvette Club presents its All Car Show at 10000 Allentown Road in Fort Washington. The show runs from 8 AM to 3 PM, welcomes a broad range of vehicles and raises funds for local charities. The published rain date is September 26.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.