Vermont’s weirdest restaurants are not filled with artificial spectacle. Their oddness comes from old railroad cars, a former schoolhouse and ice cream creations that appear to defy gravity. Like the locations among New York’s weirdest restaurants, they turn historic buildings and eccentric ideas into memorable meals.
Here are five of Vermont’s strangest restaurants.
Casey’s Caboose in Killington
Casey’s Caboose is housed inside a 35-ton railroad snowplow car dating to around 1900.
The railcar once cleared snowdrifts from New England tracks before a derailment ended its working life. It was eventually converted into a restaurant and opened in its present form in 1981.
Customers can dine near the long row of train windows or request seats in the elevated observation area where an engineer once directed the plow.
The menu includes burgers, steaks, wings and other hearty dishes suitable for customers arriving from nearby Killington Resort.
T.J. Buckley’s in Brattleboro
T.J. Buckley’s serves sophisticated farm-to-table dinners inside a tiny vintage diner.
The restaurant occupies a 1920s Worcester Lunch Car with only a handful of tables. Its compact open kitchen places chef Michael Fuller within sight of practically every customer, turning dinner preparation into what he has called “restaurant theater.”
The nightly menu changes based on available meat, fish, vegetables and wild ingredients, many obtained from nearby farms.
Reservations are strongly recommended. A fine-dining restaurant inside a minuscule stainless-steel diner car does not leave much room for walk-ins.
Canteen Creemee Company in Waitsfield
Vermont’s “creemee” is already a regional oddity: a particularly rich form of soft-serve ice cream, often flavored with maple syrup.
Canteen Creemee Company pushes it into stranger territory.
Its signature Bad Larry is a towering vertical sundae that can arrive surrounded by cotton candy. Other rotating creations have incorporated cakes, sauces, cereal, fruit and unexpected soft-serve flavors such as Thai tea, ginger or basil.
The savory side is equally distinctive. Customers can pair the extravagant ice cream with fried chicken, cornbread pudding, a fried chicken banh mi or a grilled “kim-cheese.”
The Belfry in Montgomery Center
The Belfry serves dinner and drinks inside an 1800s one-room schoolhouse.
The building originally educated children from surrounding farms. Today, its original blackboard is still used to display restaurant specials rather than arithmetic problems.
The name references the building’s old bell tower, while the compact wooden interior retains the unmistakable proportions of a rural classroom.
Located near Jay Peak, The Belfry has become a popular après-ski destination. Students may be gone, but diners can still sit beneath the reminders of the building’s earlier life.
Blue Benn Diner in Bennington
Blue Benn is not a modern restaurant decorated to look old. It is an authentic diner car that has occupied the same Bennington site for generations.
The blue-and-cream structure was manufactured in New Jersey and transported to Vermont in the late 1940s. Inside, customers sit in narrow booths or along the counter beside tabletop jukeboxes.
Its extensive menu goes well beyond basic diner food, but the real attraction is the feeling that the entire building arrived by rail and never left.
The Blue Benn remains compact, brightly colored and unapologetically frozen in another era.
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