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
Mar
14
EVs at Poolesville Cars & Coffee
Mar 14, 2027 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
14
Cars & Coffee Ocean City
Mar 14, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
14
Cars & Coffee @ Dunkin Donuts
Mar 14, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
14
Salisbury Pit & Pub Weekly Cruise In
Mar 14, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
26
Maryland Performance Specialties Presents 4th Friday Car Cruise At The Fop
Mar 26, 2027 · Middle River, MD
Car show in Middle River, MD, featuring classic, custom, and collector vehicles on display.
Mar
27
Cars, Bikes and Coffee
Mar 27, 2027 · Gaithersburg, MD
Regular cars and coffee / cruise-in gathering in Gaithersburg, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
27
Hunt Valley Horsepower
Mar 27, 2027 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Mar
27
Thurmont Cruise-In Series
Mar 27, 2027 · Thurmont, MD
Regular cars and coffee / cruise-in gathering in Thurmont, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
28
Car People & Friends @ Brunch
Mar 28, 2027 · Boonsboro, MD
Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.
Mar
28
ESSM- Beers & Gears Monthly Car Cruise!!
Mar 28, 2027 · Stevensville, MD
Car show in Stevensville, MD, featuring classic, custom, and collector vehicles on display.
Mar
28
Cars and Coffee at the Coffee Beanery Ocean City
Mar 28, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
28
Annapolis Cars & Coffee
Mar 28, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
28
EVs at Poolesville Cars & Coffee
Mar 28, 2027 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
28
Church of The Holy Donut
Mar 28, 2027 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Apr
4
Church of The Holy Donut
Apr 4, 2027 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Apr
4
Cars and Coffee at the Coffee Beanery Ocean City
Apr 4, 2027 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Thunderhead Cruise-In
Apr 4, 2027 · Taneytown, MD
Regular cars and coffee / cruise-in gathering in Taneytown, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Salisbury Pit & Pub Weekly Cruise In
Apr 4, 2027 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Annapolis Cars & Coffee
Apr 4, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, 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.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.