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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
Sep
27
EVs at Poolesville Cars & Coffee
Sep 27, 2026 · Poolesville, MD
Regular cars and coffee / cruise-in gathering in Poolesville, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
27
ENCOUNTER 2026
Sep 27 – Sep 29, 2026 · Saint Michael's, MD
Car show in Saint Michael's, MD, featuring classic, custom, and collector vehicles on display.
Sep
27
Concours d’Elegance on Chesapeake Bay
Sep 27, 2026 · Chester, MD
Car show in Chester, MD, featuring classic, custom, and collector vehicles on display.
Sep
27
Car People & Friends @ Brunch
Sep 27, 2026 · Boonsboro, MD
Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.
Sep
27
Sykesville American Legion Fall Car Show
Sep 27, 2026 · 8:30 AM – 2 PM · Sykesville, MD
The Sykesville American Legion Fall Car Show takes place at 7327 Slacks Road in Sykesville. The show runs from 8:30 AM to 2 PM, is open to all vehicles and is hosted by Royal GTO's. The published rain date is October 4.
Sep
27
ESSM- Beers & Gears Monthly Car Cruise!!
Sep 27, 2026 · Stevensville, MD
Car show in Stevensville, MD, featuring classic, custom, and collector vehicles on display.
Sep
27
19th Annual St Michaels Concours d'Elegance
Sep 27, 2026 · Chester, MD
Car show in Chester, MD, featuring classic, custom, and collector vehicles on display.
Sep
28
Austin Healey Sports & Touring Club Encounter 2026
Sep 28, 2026 · Saint Michaels, MD
Car show in Saint Michaels, MD, featuring classic, custom, and collector vehicles on display.
Sep
29
Austin Healey Sports & Touring Club Encounter 2026
Sep 29, 2026 · Saint Michaels, MD
Car show in Saint Michaels, MD, featuring classic, custom, and collector vehicles on display.
Sep
30
Bring Your Wheels To Deale Car Show
Sep 30, 2026 · Deale, MD
Car show in Deale, MD, featuring classic, custom, and collector vehicles on display.
Oct
2
Street Survivors Friday Night Cruise-Ins
Oct 2, 2026 · Glen Burnie, MD
Car show in Glen Burnie, MD, featuring classic, custom, and collector vehicles on display.
Oct
2
Street Survivors of Maryland Cruise Night
Oct 2, 2026 · Glen Burnie, MD
Regular cars and coffee / cruise-in gathering in Glen Burnie, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
2
Friday Cruise Nights
Oct 2, 2026 · glen burnie, MD
Car show in glen burnie, MD, featuring classic, custom, and collector vehicles on display.
Oct
2
Kensington Car Show
Oct 2, 2026 · Kensington, MD
Car show in Kensington, MD, featuring classic, custom, and collector vehicles on display.
Oct
3
Hunt Valley Horsepower
Oct 3, 2026 · Hunt Valley, MD
Car show in Hunt Valley, MD, featuring classic, custom, and collector vehicles on display.
Oct
3
Sun City Cruisers Fall Show
Oct 3, 2026 · 10 AM – 2 PM · Rising Sun, MD
Sun City Cruisers hosts its Fall Show at American Legion Post 194, 338 E. Main Street in Rising Sun. The show runs from 10 AM to 2 PM.
Oct
3
Columbia Cruise Night
Oct 3, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
3
Alyssa Richards Memorial Car & Bike Show
Oct 3, 2026 · 9 AM – 3 PM · Taneytown, MD
The Alyssa Richards Memorial Car & Bike Show takes place at Taneytown Memorial Park from 9 AM to 3 PM. Cars and motorcycles are welcome for the memorial automotive event. The published rain date is October 4.
Oct
3
Lost 50’s Custom Car Club Of Maryland Cruise-Ins
Oct 3, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Oct
3
Three Brothers Italian Restaurant Columbia Cruise Night
Oct 3, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, 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.