GarageCherries
Chesapeake, VA Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Chesapeake, Virginia.
12 upcoming events in Chesapeake
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 Chesapeake · Oct 16–Oct 18
Oct
17
River Oak C4 Cruise-In
Oct 17, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Rollin Legends Meet & Greet @ Bubba's 33
Oct 18, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Chesapeake
Oct
17
River Oak C4 Cruise-In
Oct 17, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
18
Rollin Legends Meet & Greet @ Bubba's 33
Oct 18, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
24
Cars ‘n’ Coffee Chesapeake
Oct 24, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Nov
7
Cars and Coffee Norfolk Goes to Chesapeake
Nov 7, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Nov
7
8th Annual Southern Chevrolet Custom Car Show
Nov 7, 2026 · Chesapeake, VA
Car show in Chesapeake, VA, featuring classic, custom, and collector vehicles on display.
Nov
14
8th Annual Southern Chevrolet Custom Car Show
Nov 14, 2026 · Chesapeake, VA
Car show in Chesapeake, VA, featuring classic, custom, and collector vehicles on display.
Nov
14
Cars And Coffee Chesapeake
Nov 14, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Dec
5
Cars and Coffee Norfolk Goes to Chesapeake
Dec 5, 2026 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Jan
9
Cars And Coffee Chesapeake
Jan 9, 2027 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Mar
13
Cars And Coffee Chesapeake
Mar 13, 2027 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Apr
10
Cars And Coffee Chesapeake
Apr 10, 2027 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
Jun
12
Cars And Coffee Chesapeake
Jun 12, 2027 · Chesapeake, VA
Regular cars and coffee / cruise-in gathering in Chesapeake, VA, drawing classic cars, hot rods, and collector vehicles.
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.