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
Jan
10
Cars & Coffee Ocean City
Jan 10, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Salisbury Pit & Pub Weekly Cruise In
Jan 10, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Church of The Holy Donut
Jan 10, 2027 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Jan
10
Annapolis Cars & Coffee
Jan 10, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Cars and Coffee at the Coffee Beanery Ocean City
Jan 10, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Cars & Coffee @ Dunkin Donuts
Jan 10, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
EVs at Poolesville Cars & Coffee
Jan 10, 2027 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, 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.
Jan
13
Bring Your Wheels To Deale Car Show
Jan 13, 2027 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Jan
14
Brunetti’s Saturday Night Cruise-In
Jan 14, 2027 · Mechanicsville, MD
Regular cars and coffee / cruise-in gathering in Mechanicsville, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
16
Hunt Valley Horsepower
Jan 16, 2027 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Jan
16
Columbia Cruise Night
Jan 16, 2027 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
17
Cars & Coffee Ocean City
Jan 17, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
17
Salisbury Pit & Pub Weekly Cruise In
Jan 17, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
17
Cars & Coffee @ Dunkin Donuts
Jan 17, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
24
Car People & Friends @ Brunch
Jan 24, 2027 · Boonsboro, MD
Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.
Jan
31
ESSM- Beers & Gears Monthly Car Cruise!!
Jan 31, 2027 · Stevensville, MD
Car show in Stevensville, MD, featuring classic, custom, and collector vehicles on display.
Feb
3
Bring Your Wheels To Deale Car Show
Feb 3, 2027 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Feb
7
Cars & Coffee @ Dunkin Donuts
Feb 7, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Feb
7
Cars & Coffee Ocean City
Feb 7, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, 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.