GarageCherries
Vermont Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Vermont for 2026.
Browse cars for sale in Vermont →Get this weekend's car shows near you, every Thursday
Just your email and ZIP — shows within 50 miles, no account needed.
Filters
Narrow the events below by city, ZIP, event type, or date.
Upcoming Events
Dec
3
Hemmings Cruise-Ins’ & Thursday Night Live Music Series!
Dec 3, 2026 · Bennington, VT
Car show in Bennington, VT, featuring classic, custom, and collector vehicles on display.
Dec
5
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Dec 5, 2026 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
Mar
6
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Mar 6, 2027 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
Mar
25
Hemmings Cruise-Ins’ & Thursday Night Live Music Series!
Mar 25, 2027 · Bennington, VT
Car show in Bennington, VT, featuring classic, custom, and collector vehicles on display.
Apr
3
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Apr 3, 2027 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
May
20
Hemmings Cruise-Ins’ & Thursday Night Live Music Series!
May 20, 2027 · Bennington, VT
Car show in Bennington, VT, featuring classic, custom, and collector vehicles on display.
Jun
17
Hemmings Cruise-Ins’ & Thursday Night Live Music Series!
Jun 17, 2027 · Bennington, VT
Car show in Bennington, VT, featuring classic, custom, and collector vehicles on display.
Cars for sale near Vermont
1966 Ford Mustang Convertible
1972 Austin Mini Clubman Wagon
2014 Chevrolet CAMARO 2SS Coupe
Good1977 Ford bronco
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.