GarageCherries
Chesterfield, VA Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Chesterfield, Virginia.
15 upcoming events in Chesterfield
Browse cars for sale in Virginia →Get this weekend's car shows near you, every Thursday
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This Weekend in Chesterfield · Oct 16–Oct 18
Oct
17
Bethia UMC Vendor Fair and Car and Bike Cruise-In
Oct 17, 2026 · 9 AM – 3 PM · Chesterfield, VA
Family-fun community day at Bethia UMC featuring unique craft vendors alongside a car and motorcycle cruise-in. No registration fee, free admission.
Oct
18
Jackie D’s Coffee, Cruise In, & Flea Market
Oct 18, 2026 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Upcoming Events in Chesterfield
Oct
17
Bethia UMC Vendor Fair and Car and Bike Cruise-In
Oct 17, 2026 · 9 AM – 3 PM · Chesterfield, VA
Family-fun community day at Bethia UMC featuring unique craft vendors alongside a car and motorcycle cruise-in. No registration fee, free admission.
Oct
18
Jackie D’s Coffee, Cruise In, & Flea Market
Oct 18, 2026 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Oct
24
12th Annual Rebellion Car, Truck and Bike Show
Oct 24, 2026 · 9 AM – 5 PM · Chesterfield, VA
12th Annual Rebellion Car, Truck and Bike Show at Pocahontas State Park. $25 show registration, open to all makes, models, and styles. Over 100 custom awards, entertainment all day, vendors, charity raffle, and a Halloween costume contest at 3 PM.
Nov
14
Chester Rotary Annual Fall Festival Veteran's Car Show
Nov 14, 2026 · 12 AM – 4 PM · Chesterfield, VA
Chester Rotary's Annual Fall Festival Veteran's Car Show at Chesterfield Central Public Library. Free community event with children's activities. $20 advance registration, $25 day-of. Vendors, food trucks, 50/50 raffle, and trophies (fan favorite, best in show, best engine, best interior, best exterior, judge's choice across three eras). Half of 50/50 proceeds support Vets on Track and First Responders.
Nov
22
Jackie D’s Coffee, Cruise In, & Flea Market
Nov 22, 2026 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Nov
29
Jackie D’s Coffee, Cruise In, & Flea Market
Nov 29, 2026 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Dec
27
Jackie D’s Coffee, Cruise In, & Flea Market
Dec 27, 2026 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Jan
3
Jackie D’s Coffee, Cruise In, & Flea Market
Jan 3, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Jan
10
Jackie D’s Coffee, Cruise In, & Flea Market
Jan 10, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Feb
28
Jackie D’s Coffee, Cruise In, & Flea Market
Feb 28, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Mar
14
Jackie D’s Coffee, Cruise In, & Flea Market
Mar 14, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Mar
28
Jackie D’s Coffee, Cruise In, & Flea Market
Mar 28, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Apr
18
Jackie D’s Coffee, Cruise In, & Flea Market
Apr 18, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
May
23
Jackie D’s Coffee, Cruise In, & Flea Market
May 23, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, VA, drawing classic cars, hot rods, and collector vehicles.
Jun
13
Jackie D’s Coffee, Cruise In, & Flea Market
Jun 13, 2027 · Chesterfield, VA
Regular cars and coffee / cruise-in gathering in Chesterfield, 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.