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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
Oct
11
Salisbury Pit & Pub Weekly Cruise In
Oct 11, 2026 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
11
EVs at Poolesville Cars & Coffee
Oct 11, 2026 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
11
Church of The Holy Donut
Oct 11, 2026 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Oct
14
Bring Your Wheels To Deale Car Show
Oct 14, 2026 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Oct
16
Street Survivors Friday Night Cruise-Ins
Oct 16, 2026 · Glen Burnie, MD
Car show in Glen Burnie, MD, featuring classic, custom, and collector vehicles on display.
Oct
16
Street Survivors of Maryland Cruise Night
Oct 16, 2026 · Glen Burnie, MD
Regular cars and coffee / cruise-in gathering in Glen Burnie, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Friday Cruise Nights
Oct 16, 2026 · glen burnie, MD
Car show in glen burnie, MD, featuring classic, custom, and collector vehicles on display.
Oct
17
Potomac Day Classic Car Show
Oct 17, 2026 · Potomac, MD
Car show in Potomac, MD, featuring classic, custom, and collector vehicles on display.
Oct
17
Benson-Hammond House Cruisin’
Oct 17, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
17
The Damascus Cars and Coffee
Oct 17, 2026 · Damascus, MD
Regular cars and coffee / cruise-in gathering in Damascus, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
17
Hunt Valley Horsepower
Oct 17, 2026 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Oct
17
Waldorf Classic Car Show Spooky Edition
Oct 17, 2026 · 12 PM – 6 PM · Waldorf, MD
The Waldorf Classic Car Show returns with its Spooky Edition at 2936 Festival Way in Waldorf. The Halloween-season automotive show runs from noon to 6 PM. The published rain date is October 24.
Oct
17
Lost 50’s Custom Car Club Of Maryland Cruise-Ins
Oct 17, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
17
Shops At Waldorf Center Classic Car/Bike/Truck Show
Oct 17, 2026 · Waldorf, MD
Car show in Waldorf, MD, featuring classic, custom, and collector vehicles on display.
Oct
17
Car Show at Essex Skypark
Oct 17, 2026 · Essex, MD
Car show in Essex, MD, featuring classic, custom, and collector vehicles on display.
Oct
18
Cars and Coffee at the Coffee Beanery Ocean City
Oct 18, 2026 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Cars & Coffee Ocean City
Oct 18, 2026 · Ocean City, MD
Regular cars and coffee / cruise-in gathering in Ocean City, MD, drawing classic cars, hot rods, and collector vehicles.
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
Annapolis Cars & Coffee
Oct 18, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Cars & Coffee @ Dunkin Donuts
Oct 18, 2026 · Salisbury, MD
Regular cars and coffee / cruise-in gathering in Salisbury, 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.