11 of the Weirdest Vermont Roadside Attractions Worth Stopping For

Vermont may be known for its maple syrup, rolling hills, and peaceful small towns, but the Green Mountain State also hides some truly strange and quirky roadside gems.

Whether you’re on a road trip or just driving through, these offbeat stops offer the perfect chance to stretch your legs and snap a photo. Here are 11 of the weirdest roadside attractions in Vermont that are totally worth pulling over for.

1. The World’s Tallest Filing Cabinet – Burlington

Yes, you read that right. In an empty lot in Burlington stands a 38-foot-tall stack of filing cabinets. It’s an odd art installation called “File Under So. Co., Waiting for…,” meant to represent government red tape. Strange? Absolutely. But it’s also weirdly fascinating.

2. Ben & Jerry’s Flavor Graveyard – Waterbury

If you’ve ever wondered what happens to retired ice cream flavours, Ben & Jerry’s has the answer. Behind their factory in Waterbury, you’ll find a small “graveyard” with headstones for discontinued flavours like “Wavy Gravy” and “Peanut Butter & Jelly.” It’s both hilarious and oddly emotional.

3. The Whale in the Woods – Norwich

Deep in the woods near Norwich lies a massive concrete whale. No one’s quite sure why it’s there, but it’s become a local legend. Part random art, part mysterious relic—it’s the kind of thing you have to see to believe.

4. Bread and Puppet Museum – Glover

This isn’t your average museum. Located in a massive barn, it’s filled with giant puppets, masks, and political art from the famous Bread and Puppet Theater. The vibe is equal parts creepy, creative, and thought-provoking.

5. Vermontasaurus – Post Mills

Who needs a dinosaur park when you’ve got Vermontasaurus? Built entirely from scrap wood by a local man, this giant dinosaur sculpture towers over the landscape. It’s DIY art at its weirdest—and most wonderful.

6. The Lincoln General Store’s Odd Sign Collection – Lincoln

Outside this quiet country store hangs a collection of strange, funny, and completely random signs. Some make you laugh, others leave you scratching your head. It’s the kind of place that makes a simple stop feel like a quirky experience.

7. Floating Bridge – Brookfield

A floating bridge? In Vermont? Yup. This unusual bridge, made of floating pontoons, lets you drive or walk right over Sunset Lake. It’s one of only a few in the country—and feels more like something from a movie.

8. Giant Gorilla Holding a VW Bug – Leicester

On Route 7 stands a giant black gorilla with one hand raised high, gripping a full-size Volkswagen Beetle. It’s part of a local mini-golf course and ice cream shop, but the sculpture itself is pure roadside madness.

9. American Museum of Fly Fishing – Manchester

Only in Vermont would you find a whole museum dedicated to the art and history of fly fishing. Even if you’re not into fishing, the old rods, photos, and stories make this a weirdly charming detour.

10. The Museum of Everyday Life – Glover

This self-service roadside museum celebrates the boring stuff in life—like toothbrushes, safety pins, and pencil sharpeners. It sounds dull, but the displays are strangely poetic and philosophical. Plus, it’s donation-based and always open.

11. Giant Painted Rocking Horse – Barre

In a quiet neighbourhood in Barre, someone built a massive rocking horse and painted it bright red. It doesn’t rock, but it sure catches your attention. It’s just sitting there—huge, unexpected, and delightfully weird.

Vermont may be small, but it packs a punch when it comes to offbeat roadside attractions. These quirky spots give your road trip a fun twist and show off the state’s unique character.

From giant puppets to ice cream graveyards, there’s no shortage of surprises waiting along Vermont’s peaceful backroads. So next time you hit the road, take the scenic route—and don’t forget your camera.

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