GarageCherries
Vermont Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Vermont for 2026.
Browse cars for sale in Vermont →Filters
Narrow the events below by city, ZIP, or event type.
Featured Events
Oct
11
5th Annual Middlebury Car Show & Fall Festival
Oct 11, 2026 · 10 AM – 3 PM · Middlebury, VT
The 5th Annual Middlebury Car Show & Fall Festival takes over Triangle Park and Main Street in downtown Middlebury from 10 AM to 3 PM. Main Street closes to welcome up to 75 classic cars and trucks. The free public event also includes more than 30 vendors, food trucks, music and children's activities.
Upcoming Events
Sep
27
5th Annual Snake Mountain Car Show
Sep 27, 2026 · 8 AM – 3 PM · New Haven, VT
The 5th Annual Snake Mountain Car Show takes place at the Addison County Fair & Field Days grounds in New Haven. Gates open at 8 AM and the show continues until 3 PM. Participants must be on the field by 11 AM to be eligible for awards.
Oct
3
Cars & Coffee Middlebury
Oct 3, 2026 · 8 AM – 10 AM · Middlebury, VT
Cars & Coffee Middlebury returns to the A&W Drive-In on Route 7 for its October gathering. The first-Saturday automotive meet runs from 8 AM to 10 AM.
Oct
3
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Oct 3, 2026 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
Oct
13
Island Ice Cream Car Meet
Oct 13, 2026 · 6 PM – 8 PM · Williston, VT
The October Island Ice Cream Car Meet takes place at 21 Commerce Street in Williston from 6 PM to 8 PM. The recurring second-Tuesday event brings together local automotive enthusiasts.
Oct
24
Cars & Coffee - Manchester, Vermont
Oct 24, 2026 · Manchester Center, VT
Regular cars and coffee / cruise-in gathering in Manchester Center, VT, drawing classic cars, hot rods, and collector vehicles.
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
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.
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.
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.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.