GarageCherries
Vermont Car Shows & Events
Classic car shows, auctions, swap meets, and cruise nights in Vermont for 2026.
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Past Events
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
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
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
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
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
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
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.
Aug
11
Island Ice Cream Car Meet
Aug 11, 2026 · 6 PM – 8 PM · Williston, VT
The monthly Island Ice Cream Car Meet takes place at 21 Commerce Street in Williston. The gathering runs from 6 PM to 8 PM and brings together local automotive enthusiasts on the second Tuesday of the month.
Dates are subject to change. Verify with organizers before making travel arrangements. GarageCherries is not affiliated with any listed event.