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Vermont
Bennington County

Old Bennington

Attractions and Places To See around Old Bennington - Top 7

Best attractions and places to see around Old Bennington include historical landmarks, cultural sites, and scenic trails. This Vermont region is known for its preserved historic village, offering a tangible connection to early American history. Visitors can explore a mix of man-made monuments, historic bridges, and natural viewpoints. The area provides opportunities for both historical exploration and outdoor activities.

Best attractions and places to see around Old Bennington

  • The most popular attractions is Bennington Battle Monument, a man-made monument…

Last updated: June 28, 2026

Carriage Road (Grove Road)

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The Carriage Road is how most begin (and often end as well) their hike in the scenic, pastoral Mile-Around-Woods area. This bucolic segment of trail is west of the Park-McCullough …

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Silk Covered Bridge

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The Silk Covered Bridge, part of Silk Road, spans the Walloomsac River connecting Bennington and North Bennington, Vermont. Constructed in 1840, this Town lattice truss bridge is one of three …

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Harmon Hill

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The top of Harmon Hill is covered by huge green ferns and dotted with trees, which stands in stark contrast to the rest of the area which is densely forested. …

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Bennington Battle Monument

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come between 10 and 5 to see the top of the monument.

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Wooden Footbridge

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Right next to VT-9 on the Long/ Appalachian Trail is a small stream with wooden foot bridge. This is a nice place to fill water bottles and snap a few …

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Alex
January 26, 2024, Bennington Battle Monument

The Bennington Battle Monument, erected in 1891, commemorates the Revolutionary War's Battle of Bennington in Vermont. Standing at 306 feet, it symbolizes the victory against British forces. Funded by patriotic citizens, the monument is a testament to the community's dedication to preserving and honoring its historical legacy.

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Alex
January 26, 2024, Silk Covered Bridge

The Silk Covered Bridge, part of Silk Road, spans the Walloomsac River connecting Bennington and North Bennington, Vermont. Constructed in 1840, this Town lattice truss bridge is one of three in the vicinity. Its historical significance led to its inclusion in the National Register of Historic Places in 1973.

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The Carriage Road is how most begin (and often end as well) their hike in the scenic, pastoral Mile-Around-Woods area. This bucolic segment of trail is west of the Park-McCullough Historic Governor's Mansion and follows a treed, old carriage road through some farm fields. This section of the Mile-Around-Woods is particurlaly stunning in the fall when the leaves are changing from green to bright hues of orange, yellow, and red.

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Right next to VT-9 on the Long/ Appalachian Trail is a small stream with wooden foot bridge. This is a nice place to fill water bottles and snap a few photos before continuing onward on the Long/ Appalachian Trail toward the Melville-Nauheim Shelter and Glastenbury Mountain or crossing the road toward the scenic Harmon Hill.

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Jamie S.
April 7, 2023, Harmon Hill

The top of Harmon Hill is covered by huge green ferns and dotted with trees, which stands in stark contrast to the rest of the area which is densely forested. This is because the summit of Harmon Hill is kept clear by controlled burns that allow for fantastic views of the town of Bennington and the surrounding area. This lush meadow is a perfect place to rest, admire the views, and sip some water before continuing on your hike.

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Wonderful view from the monument into the distance.

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come between 10 and 5 to see the top of the monument.

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Frequently Asked Questions

What historical landmarks can I visit in Old Bennington?

Old Bennington is rich in history. You can visit the Bennington Battle Monument, a 306-foot structure commemorating a pivotal Revolutionary War victory. Another significant site is the Old First Church and its adjacent cemetery, which is the final resting place of poet Robert Frost. The historic Walloomsac Inn, built in 1764, is Vermont's oldest inn, though not currently open to the public. You can also see the site of the Catamount Tavern, a gathering place for the Green Mountain Boys.

Are there any family-friendly attractions in Old Bennington?

Yes, several attractions are suitable for families. The Bennington Battle Monument is family-friendly and offers panoramic views. The Silk Covered Bridge is a historical site that families can enjoy exploring. For a scenic walk, the Carriage Road (Grove Road), part of the Mile-Around-Woods, is a pastoral trail perfect for all ages, especially beautiful in the fall.

What outdoor activities and trails are available near Old Bennington?

The area around Old Bennington offers various outdoor activities, particularly hiking. You can explore trails like the Carriage Road (Grove Road), which is an easy walk through farm fields. For more challenging hikes, consider routes up Harmon Hill, which offers fantastic views. The Bennington Area Trail System (BATS) on Mount Anthony provides options for hiking, mountain biking, and winter activities. You can find more details on specific routes in the Hiking around Old Bennington guide.

Where can I find scenic viewpoints in Old Bennington?

For breathtaking views, head to the Bennington Battle Monument. You can ride an elevator to the top for spectacular panoramic vistas of Vermont, New York, and Massachusetts. Another excellent spot is the summit of Harmon Hill, which offers clear views of the town of Bennington and the surrounding area.

Are there any wheelchair-accessible attractions in Old Bennington?

Yes, the Bennington Battle Monument is noted as wheelchair accessible, allowing visitors to experience its historical significance and panoramic views.

What cultural sites are worth visiting in the Old Bennington area?

Beyond historical landmarks, the Bennington Museum, located near Old Bennington, offers a deep dive into the region's art and history. It houses an extensive collection, including Grandma Moses paintings and one of the oldest American flags. The Old First Church, recognized as Vermont's Colonial Shrine, is also a significant cultural site with its Federal church architecture.

Can I visit Robert Frost's grave in Old Bennington?

Yes, the grave of renowned American poet Robert Frost is located in the cemetery adjacent to the Old First Church in Old Bennington. It is a significant draw for literary enthusiasts.

What is the best way to explore the historic village of Old Bennington?

The historic village of Old Bennington is best explored on foot. Self-guided walking tours are available that highlight its historic buildings and rich past, including a stroll along Monument Avenue to see many historic homes from various architectural eras.

Are there cycling routes available near Old Bennington attractions?

Yes, there are several cycling routes that pass by or near attractions in Old Bennington. For example, you can find routes like the 'Bennington Battle Monument – Silk Covered Bridge loop from Bennington' for road cycling, or an 'easy' touring bicycle route like the 'Bennington Battle Monument loop from Old Bennington'. More detailed routes can be found in the Road Cycling Routes around Old Bennington guide and the Cycling around Old Bennington guide.

What is the significance of the Silk Covered Bridge?

The Silk Covered Bridge is a historical site constructed in 1840. This Town lattice truss bridge spans the Walloomsac River and is one of three in the vicinity. Its historical importance led to its inclusion in the National Register of Historic Places in 1973.

What do visitors enjoy most about the attractions in Old Bennington?

Visitors particularly appreciate the historical significance and the stunning views. The Bennington Battle Monument is praised for its wonderful distant views. The Carriage Road (Grove Road) is noted for its bucolic scenery, especially in the fall when the leaves change to vibrant colors. The area's preserved historic village offers a tangible connection to early American and Vermont history.

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Still not found the Highlight you’re looking for? See guides of the top attractions in other regions:

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