GarageCherries
Gloucester, VA Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Gloucester, Virginia.
6 upcoming events in Gloucester
Browse cars for sale in Virginia →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 Gloucester · Oct 16–Oct 18
Oct
16
Let's Talk Cars Friday Night Cruise-in
Oct 16, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Middle Peninsula Classic Cruisers Let’s Talk Cars Friday Night Cruise-In
Oct 16, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Gloucester
Oct
16
Let's Talk Cars Friday Night Cruise-in
Oct 16, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
16
Middle Peninsula Classic Cruisers Let’s Talk Cars Friday Night Cruise-In
Oct 16, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
23
Let's Talk Cars Friday Night Cruise-in
Oct 23, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
23
Middle Peninsula Classic Cruisers Let’s Talk Cars Friday Night Cruise-In
Oct 23, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
30
Let's Talk Cars Friday Night Cruise-in
Oct 30, 2026 · Gloucester, VA
Regular cars and coffee / cruise-in gathering in Gloucester, VA, drawing classic cars, hot rods, and collector vehicles.
Nov
7
Gloucester Classic Car Show
Nov 7, 2026 · Gloucester, VA
Car show in Gloucester, VA, featuring classic, custom, and collector vehicles on display.
Car Shows in Nearby Cities
Cars for sale in Virginia
1967 Ford Mustang Sport Sprint Coupe
1973 Volkswagen Thing
1965 Chevrolet Impala SS
Good1980 Chevrolet Corvette T-top
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.