GarageCherries
Maryland Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Maryland for 2026.
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Past Events
Sep
26
Pleasant Valley Car Show & Flea Market
Sep 26, 2026 · 9 AM – 3 PM · Westminster, MD
Pleasant Valley Community Fire Company hosts its annual Car Show & Flea Market at 2030 S. Pleasant Valley Road in Westminster. The show runs from 9 AM to 3 PM and is open to cars, trucks, SUVs, customs and hot rods. The event is held in memory of fire department life member and veteran Donald 'Sox' Bowersox, with proceeds benefiting the fire company.
Sep
26
Three Brothers Italian Restaurant Columbia Cruise Night
Sep 26, 2026 · Columbia, MD
Regular cars and coffee / cruise-in gathering in Columbia, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
26
The 36th Annual Corvettes at Westridge
Sep 26, 2026 · Frederick, MD
Car show in Frederick, MD, featuring classic, custom, and collector vehicles on display.
Sep
26
Show 4 A Cause
Sep 26, 2026 · 9 AM – 1 PM · Perryville, MD
Show 4 A Cause takes place at Hollywood Casino, 1201 Chesapeake Overlook Parkway in Perryville. The show runs from 9 AM to 1 PM and benefits Upper Bay Counseling. Passion 4 Pavement hosts the automotive event.
Sep
26
Benson-Hammond House Cruisin’
Sep 26, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
26
Thurmont Cruise-In Series
Sep 26, 2026 · Thurmont, MD
Regular cars and coffee / cruise-in gathering in Thurmont, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
26
47th Annual "MGs On The Rocks" British Car Show & Parts Market
Sep 26, 2026 · Street, MD
Car show in Street, MD, featuring classic, custom, and collector vehicles on display.
Sep
26
2026 Classic Car Cruise Nights at Harford Vineyard
Sep 26, 2026 · Forest Hill, MD
Car show in Forest Hill, MD, featuring classic, custom, and collector vehicles on display.
Sep
26
4th Annual All Cars Show
Sep 26, 2026 · Waldorf, MD
Regular cars and coffee / cruise-in gathering in Waldorf, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
26
2026 Chesapeake Car Show
Sep 26, 2026 · Pasadena, MD
Car show in Pasadena, MD, featuring classic, custom, and collector vehicles on display.
Sep
26
Lead Don't Follow Foundation Car Show 5
Sep 26, 2026 · 10 AM – 3 PM · Boonsboro, MD
The Lead Don't Follow Foundation hosts Car Show 5 at the Washington County Agricultural Education Center, 7313 Sharpsburg Pike in Boonsboro. The show runs from 10 AM to 3 PM and features multiple vehicle award categories and family activities while benefiting Ladders to Leaders.
Sep
26
Pleasant Valley Fire Company 2nd Annual Car Show
Sep 26, 2026 · Upperco, MD
Car show in Upperco, MD, featuring classic, custom, and collector vehicles on display.
Sep
26
Lost 50’s Custom Car Club Of Maryland Cruise-Ins
Sep 26, 2026 · Linthicum, MD
Regular cars and coffee / cruise-in gathering in Linthicum, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
26
Cars, Bikes and Coffee
Sep 26, 2026 · Gaithersburg, MD
Regular cars and coffee / cruise-in gathering in Gaithersburg, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
25
19th Annual St. Michaels Concours d’Elegance on Chesapeake Bay
Sep 25 – Sep 26, 2026 · Chester, MD
Regular cars and coffee / cruise-in gathering in Chester, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
25
Friday Cruise Nights
Sep 25, 2026 · glen burnie, MD
Car show in glen burnie, MD, featuring classic, custom, and collector vehicles on display.
Sep
25
Street Survivors of Maryland Cruise Night
Sep 25, 2026 · Glen Burnie, MD
Regular cars and coffee / cruise-in gathering in Glen Burnie, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
25
Maryland Performance Specialties Presents 4th Friday Car Cruise At The Fop
Sep 25, 2026 · Middle River, MD
Car show in Middle River, MD, featuring classic, custom, and collector vehicles on display.
Sep
22
Porsche Touring Crew – Dutch’s at Silver Tree – September 22nd
Sep 22, 2026 · Oakland, MD
Regular cars and coffee / cruise-in gathering in Oakland, MD, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Annapolis Cars & Coffee
Sep 20, 2026 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, 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.