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

Car Show

Car People & Friends @ Brunch

Sep 27, 2026 · Boonsboro, MD

Car show in Boonsboro, MD, featuring classic, custom, and collector vehicles on display.

Sep

Car Show

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

–Sep 29

Car Show

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

Car Show

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

Car Show

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

Car Show

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

Car Show

2026 Chesapeake Car Show

Sep 26, 2026 · Pasadena, MD

Car show in Pasadena, MD, featuring classic, custom, and collector vehicles on display.

Sep

Cruise Night

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

Car Show

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

Cruise Night

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

Cruise Night

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

Car Show

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

Cruise Night

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

Cruise Night

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

Car Show

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

Car Show

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

Car Show