GarageCherries
Annapolis, MD Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Annapolis, Maryland.
11 upcoming events in Annapolis
Browse cars for sale in Maryland →Get this weekend's car shows near you, every Thursday
Just your email and ZIP — shows within 50 miles, no account needed.
This Weekend in Annapolis · Oct 16–Oct 18
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.
Upcoming Events in Annapolis
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.
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
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.
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.
Jan
3
Annapolis Cars & Coffee
Jan 3, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Annapolis Cars & Coffee
Jan 10, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Feb
28
Annapolis Cars & Coffee
Feb 28, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Mar
28
Annapolis Cars & Coffee
Mar 28, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Apr
4
Annapolis Cars & Coffee
Apr 4, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Jun
6
Annapolis Cars & Coffee
Jun 6, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Jun
13
Annapolis Cars & Coffee
Jun 13, 2027 · Annapolis, MD
Regular cars and coffee / cruise-in gathering in Annapolis, MD, drawing classic cars, hot rods, and collector vehicles.
Car Shows in Nearby Cities
Cars for sale near Maryland
1969 Ford Mustang Mach 1 Cobra Jet
1967 Ford Mustang Sport Sprint Coupe
1973 Volkswagen Thing
1965 Chevrolet Impala SS
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.