One of my absolute favorite things to do when I am out riding around is to find roadside oddities and attractions. I have been known to make many a U-turn while driving down the road. This page will be dedicated to any roadside attractions that I have found in the state of Vermont.
It will be a constant work in progress as I will add new oddities and attractions every time I find one. Make sure you check back often for new updates. Better yet, subscribe to my site so you will be informed each time content is added. Don’t worry, no spam here. I only send out emails once a week, usually on Fridays. Subscribe Here
Cornish-Windsor Covered Bridge
Location: 47-41 Bridge Street
City: Windsor
Region of State Located: East/Central
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The Historic Cornish-Windsor Covered Bridge is a massive piece of engineering history that spans the Connecticut River, connecting Windsor, Vermont, to Cornish, New Hampshire. Built in 1866, it was the longest covered bridge in the United States for over a century and remains a stunning example of the Town lattice truss design.
Historic Longevity: It is the fourth bridge to stand at this location, with its predecessors all falling victim to the river’s floods; the current 1866 version has survived for over 150 years, earning it a spot on the National Register of Historic Places.
Engineering Marvel: Stretching approximately 449 feet, this timber-framed masterpiece is held together by wooden trunnels and remains open to automobile traffic, allowing you to experience the rhythmic “clack-clack” of tires on wood just as travelers did 150 years ago.
Dual-State Landmark: Because the state line is actually the low-water mark on the Vermont side, the bridge technically sits mostly in New Hampshire, though it has long been a symbol of the shared history and craftsmanship of both states.
Photographer’s Dream: The bridge’s weathered grey siding and classic portal design are framed perfectly by the river and the lush Vermont hills, making it a premier spot for capturing that quintessential New England “covered bridge” aesthetic.
Tafstville Covered Bridge
Location: Covered Bridge Rd
City: Woodstock
Region of State Located: East/Central
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The Historic Taftsville Covered Bridge is a striking deep-red landmark spanning the Ottauquechee River between Woodstock and Taftsville. Completed in 1836, it is one of the oldest covered bridges in Vermont and stands out for its rare “modified arch” construction, a local variation of the more common truss designs found throughout New England.
Scenic Surroundings: The site offers easy roadside pull-offs where you can capture the bridge alongside the rushing river and the historic brick power generation building nearby.
Distinctive Engineering: Unlike many bridges that rely on a standard lattice, the Taftsville bridge uses a heavy timber frame reinforced by massive hand-hewn arches, a testament to the early 19th-century craftsmanship of builder Solomon Emmons III.
Vibrant Aesthetic: Its bold red exterior provides a dramatic contrast against the white water of the Taftsville dam located just downstream, making it a favorite subject for landscape photography.
Resilient History: The bridge has survived over 180 years of Vermont winters and floods, including significant restoration work after Tropical Storm Irene in 2011, ensuring it remains a functional piece of the state’s transportation heritage.
Vermont Teddy Bear
Location: RT 7 and S. Park Rd
City: Shelburne
Region of State Located: North/West
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Located in Shelburne, the Vermont Teddy Bear Factory is guarded by one of the most huggable roadside icons in New England. Sitting right out front to greet visitors is a massive, multi-colored “stuffed” teddy bear, a larger-than-life version of their famous handcrafted bears.
Gateway to the Factory: Beyond the giant bear, the site offers “behind-the-scenes” tours where you can see the “Bear Hospital” and the production line where every bear is cut, sewn, and stuffed by hand.
A Patchwork Giant: This iconic bear is easily recognizable by its vibrant, patchwork-style fur, mirroring the whimsical designs found inside the factory. Standing (or rather, sitting) as a permanent photo op, it has become a must-stop landmark for families and photographers traveling along Route 7.
The “Born in Vermont” Spirit: The statue represents the company’s humble beginnings in 1981, when the founder began selling bears from a pushcart on the Burlington pedestrian mall. Today, it serves as the mascot for one of the largest producers of premium teddy bears in North America.
Interactive Landmark: Unlike many “do not touch” statues, this giant bear is built for interaction. It’s a favorite spot for visitors to pose for a “bear hug” photo, capturing a bit of the playful, handcrafted charm that Vermont is known for.
Wicked Awesome BBQ Wood Carving
Location: 93 Beswick Dr
City: White River Junction
Region of State Located: Central/East
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The wood-carved pig standing guard outside Wicked Awesome BBQ is a perfect example of the rustic, “no-frills” charm that defines the best New England roadside eateries. This hand-crafted mascot, complete with the restaurant’s bold name etched into its side, serves as a literal signpost for the authentic wood-smoked flavors found within.
A Community Staple: Sitting right at the entrance, this carved mascot has become a recognizable landmark for locals and regular commuters along the nearby interstates, marking a reliable pit stop for high-quality comfort food.
A “Smoke Shack” Welcome: The pig reflects the restaurant’s roots as a traditional smoke shack, signaling to travelers that they’ve found a spot where the BBQ is prepared with patience and a focus on craftsmanship.
Artisan Roadside Decor: The weathered wood and hand-carved details of the pig make it a favorite subject for photographers looking to capture the unique character of Vermont’s local business scene.
The Scent of Hickory: Visitors often note that the sight of the carved pig is usually accompanied by the unmistakable aroma of slow-cooking brisket and pulled pork wafting from the outdoor smokers.
Woodstock Middle Covered Bridge
Location: Mountain Ave
City: Woodstock
Region of State Located: Central/East
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Located right in the heart of the village, the Historic Middle Covered Bridge is perhaps the most photographed bridge in Vermont due to its picturesque setting adjacent to the town green. While it looks like a relic from the 1800s, it was actually built in 1969 to replace an older iron bridge, making it the first covered bridge built by the state in 80 years.
Resilient Design: Despite being a modern build, it was designed with a high clearance and sturdy frame, allowing it to serve as a functional gateway to the residential side of the village.
Traditional Craftsmanship: It was constructed using a classic Town lattice truss design and authentic wooden trunnels, honoring the historic methods of the 19th-century builders.
Unique Pedestrian Lane: A distinctive feature of this bridge is the separate, narrower walkway for pedestrians, allowing you to capture interior shots of the woodwork without worrying about vehicle traffic.
Village Charm: Its location at the end of Mountain Avenue provides a stunning vista where the weathered wood of the bridge perfectly frames the colonial architecture and steeples of Woodstock.