GarageCherries
Maryland Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Maryland for 2026.
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Featured Events
Oct
8
Endless Summer Cruisin'
Oct 8 – Oct 10, 2026 · Ocean City, MD
The 29th Annual Endless Summer Cruisin' takes place October 8-11 at the Ocean City Inlet and Roland E. Powell Convention Center. Thursday, Friday and Saturday show hours are 9 AM to 5 PM, while Sunday's Inlet show runs from 9 AM to 3 PM. The multi-day automotive celebration features rods, customs, classics, specialty vehicles, displays and cruising throughout Ocean City.
Oct
17
28th Mobtown Greaseball Hot Rod & Chopper Show
Oct 17, 2026 · 11 AM – 4 PM · Dundalk, MD
The 28th Mobtown Greaseball Hot Rod & Chopper Show takes place at American Legion Post 38, 3300 Dundalk Avenue. The show runs from 11 AM to 4 PM and focuses on traditional hot rods from 1972 and earlier and vintage-style motorcycles.
Oct
17
Rockville Antique and Classic Car Show
Oct 17, 2026 · 11 AM – 3:30 PM · Rockville, MD
The Rockville Antique and Classic Car Show takes place at Rockville Civic Center Park, 603 Edmonston Drive. The public show runs from 11 AM to 3:30 PM and brings together approximately 33 car clubs with antique, classic and collector automobiles ranging from historic marques to exotic vehicles.
Nov
8
Jerry's Fall Car Show
Nov 8, 2026 · 10 AM – 3 PM · Parkville, MD
Jerry's Chevrolet hosts its Fall Car Show in Parkville. The show runs from 10 AM to 3 PM with vehicle registration from 8 AM to 10:30 AM. All makes and models are welcome, with 44 classes and nine additional award categories. Awards begin at 3 PM.
Upcoming Events
Dec
26
Hunt Valley Horsepower (Cars & Coffee)
Dec 26, 2026 · Hunt Valley, MD
Regular cars and coffee / cruise-in gathering in Hunt Valley, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
26
Columbia Cruise Night
Dec 26, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
26
Cars, Bikes and Coffee
Dec 26, 2026 · Gaithersburg, MD
Regular cars and coffee / cruise-in gathering in Gaithersburg, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Car People & Friends @ Brunch
Dec 27, 2026 · Boonsboro, MD
Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.
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.
Dec
27
Cars & Coffee Ocean City
Dec 27, 2026 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Thurmont Cruise-In Series
Dec 27, 2026 · Thurmont, MD
Regular cars and coffee / cruise-in gathering in Thurmont, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
27
ESSM- Beers & Gears Monthly Car Cruise!!
Dec 27, 2026 · Stevensville, MD
Car show in Stevensville, MD, featuring classic, custom, and collector vehicles on display.
Dec
27
Cars & Coffee @ Dunkin Donuts
Dec 27, 2026 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
30
Bring Your Wheels To Deale Car Show
Dec 30, 2026 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Jan
3
Cars & Coffee Ocean City
Jan 3, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
3
Cars & Coffee @ Dunkin Donuts
Jan 3, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
3
Thunderhead Cruise-In
Jan 3, 2027 · Taneytown, MD
Regular cars and coffee / cruise-in gathering in Taneytown, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
3
Cars and Coffee at the Coffee Beanery Ocean City
Jan 3, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
3
Church of The Holy Donut
Jan 3, 2027 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Jan
3
Annapolis Cars & Coffee
Jan 3, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Columbia Cruise Night
Jan 9, 2027 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Colonial Rodder’s 2026 Cruise-In’s
Jan 9, 2027 · Easton, MD
Regular cars and coffee / cruise-in gathering in Easton, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Hunt Valley Horsepower
Jan 9, 2027 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Jan
9
Hereford Zone Cruise In
Jan 9, 2027 · Parkton, MD
Regular cars and coffee / cruise-in gathering in Parkton, MD, drawing classic cars, hot rods, and collector vehicles.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.