GarageCherries
Middlebury, VT Car Shows & Events 2026
Classic car shows, cruise-ins, swap meets, and auctions in Middlebury, Vermont.
6 upcoming events in Middlebury
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.
Upcoming Events in Middlebury
Nov
7
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Nov 7, 2026 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
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.
Jan
2
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Jan 2, 2027 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
Feb
6
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Feb 6, 2027 · 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.
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.
Cars for sale near Vermont
FEATUREDExcellent1969 Oldsmobile Cutlass S Holiday Coupe W31
1955 Chevrolet Bel Air Sport Coupe
1931 Ford Model A Victoria Leatherback
2019 CHEVROLET MALIBU 1FL
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.