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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
Nov
7
Historic Stevensville Classic Car Show
Nov 7, 2026 · 10 AM – 3 PM · Stevensville, MD
The Historic Stevensville Classic Car Show takes place at 325 Main Street in historic Stevensville. The show runs from 10 AM to 3 PM and brings classic and collector vehicles to the historic district.
Nov
7
Chesapeake Cars and Coffee
Nov 7, 2026 · Kent Narrows, MD
Regular cars and coffee / cruise-in gathering in Kent Narrows, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
8
Church of The Holy Donut
Nov 8, 2026 · Burtonsville, MD
Car show in Burtonsville, MD, featuring classic, custom, and collector vehicles on display.
Nov
8
Annapolis Cars & Coffee
Nov 8, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
14
Hunt Valley Horsepower (Cars & Coffee)
Nov 14, 2026 · Hunt Valley, MD
Regular cars and coffee / cruise-in gathering in Hunt Valley, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
14
The Damascus Cars and Coffee
Nov 14, 2026 · Damascus, MD
Regular cars and coffee / cruise-in gathering in Damascus, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
21
New Member Party – Porsche Annapolis
Nov 21, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
21
Columbia Cruise Night
Nov 21, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
21
Hunt Valley Horsepower (Cars & Coffee)
Nov 21, 2026 · Hunt Valley, MD
Regular cars and coffee / cruise-in gathering in Hunt Valley, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
22
Car People & Friends @ Brunch
Nov 22, 2026 · Boonsboro, MD
Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.
Nov
22
EVs at Poolesville Cars & Coffee
Nov 22, 2026 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
25
Bring Your Wheels To Deale Car Show
Nov 25, 2026 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Nov
29
Town Market Coffee & Cars
Nov 29, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Nov
29
ESSM- Beers & Gears Monthly Car Cruise!!
Nov 29, 2026 · Stevensville, MD
Car show in Stevensville, MD, featuring classic, custom, and collector vehicles on display.
Dec
5
Linda’s Legacy Tour
Dec 5, 2026 · Cockeysville, MD
Regular cars and coffee / cruise-in gathering in Cockeysville, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
13
Town Market Coffee & Cars
Dec 13, 2026 · Leonardtown, MD
Regular cars and coffee / cruise-in gathering in Leonardtown, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
13
EVs at Poolesville Cars & Coffee
Dec 13, 2026 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
19
Hunt Valley Horsepower (Cars & Coffee)
Dec 19, 2026 · Hunt Valley, MD
Regular cars and coffee / cruise-in gathering in Hunt Valley, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
20
Annapolis Cars & Coffee
Dec 20, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Dec
25
Maryland Performance Specialties Presents 4th Friday Car Cruise At The Fop
Dec 25, 2026 · Middle River, MD
Car show in Middle River, MD, featuring classic, custom, and collector vehicles on display.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.