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.
Past Events
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.
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.
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
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
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.
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.
Sep
26
Car show and cruise in
Sep 26, 2026 · Brattleboro, VT
Regular cars and coffee / cruise-in gathering in Brattleboro, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
26
Cars & Coffee - Manchester, Vermont
Sep 26, 2026 · Manchester Center, VT
Regular cars and coffee / cruise-in gathering in Manchester Center, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
20
Cars & Coffee - Vermont
Sep 20, 2026 · South Burlington, VT
Regular cars and coffee / cruise-in gathering in South Burlington, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
18
–Sep 19
British Invasion (Stowe VT)
Sep 18 – Sep 19, 2026 · Stowe, VT
Regular cars and coffee / cruise-in gathering in Stowe, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
12
Upper Valley Aquatic Center September Celebration & Car Show
Sep 12, 2026 · 10 AM – 2 PM · White River Junction, VT
Upper Valley Aquatic Center hosts its September Celebration & Car Show at 100 Arboretum Lane in White River Junction. The free show runs from 10 AM to 2 PM and welcomes classic cars, hot rods, motorcycles and special RVs. The event also includes food trucks, a live DJ, children's activities, touch-a-trucks and a People's Choice-style vehicle vote, with the car show award scheduled for 1:30 PM.
Sep
10
Hemmings Cruise-Ins’ & Thursday Night Live Music Series!
Sep 10, 2026 · Bennington, VT
Car show in Bennington, VT, featuring classic, custom, and collector vehicles on display.
Sep
8
Island Ice Cream Car Meet
Sep 8, 2026 · 6 PM – 8 PM · Williston, VT
The September Island Ice Cream Car Meet takes place at 21 Commerce Street in Williston from 6 PM to 8 PM. The recurring second-Tuesday gathering brings together local automotive enthusiasts.
Sep
6
Connecticut River Valley Cars and Coffee
Sep 6, 2026 · Windsor, VT
Regular cars and coffee / cruise-in gathering in Windsor, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
6
Cars & Coffee Waitsfield
Sep 6, 2026 · 9 AM – 12 PM · Waitsfield, VT
Cars & Coffee Waitsfield takes place at Mad River Exchange, 6163 Route 100 in Waitsfield. The monthly gathering runs from 9 AM to noon and welcomes local automotive enthusiasts.
Sep
5
Cars & Coffee & Caffeine & Convertibles & Classics & Roadsters & Rockets!
Sep 5, 2026 · Middlebury, VT
Regular cars and coffee / cruise-in gathering in Middlebury, VT, drawing classic cars, hot rods, and collector vehicles.
Sep
5
Cars & Coffee Middlebury
Sep 5, 2026 · 8 AM – 10 AM · Middlebury, VT
Cars & Coffee Middlebury takes place at the A&W Drive-In on Route 7 in Middlebury. The monthly automotive gathering runs from 8 AM to 10 AM.
Aug
30
2026 Eurobuilt Car Show & Charity Auction
Aug 30, 2026 · Rutland, VT
Car show in Rutland, VT, featuring classic, custom, and collector vehicles on display.
Aug
30
Cars & Coffee - Manchester, Vermont
Aug 30, 2026 · Manchester Center, VT
Regular cars and coffee / cruise-in gathering in Manchester Center, VT, drawing classic cars, hot rods, and collector vehicles.
Aug
16
Cars & Coffee Vermont
Aug 16, 2026 · 7 AM – 9 AM · South Burlington, VT
Cars & Coffee Vermont takes place at University Mall, 155 Dorset Street in South Burlington. The morning gathering runs from 7 AM to 9 AM and welcomes automotive enthusiasts and their vehicles.
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.