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.
Last updated: June 28, 2026
Highlight (Segment) • Trail
Tip by
Highlight • Bridge
Tip by
Sign up now to discover places like this
Get recommendations on the best single tracks, peaks, & plenty of other exciting outdoor places.
Sign up for free
Highlight • Summit
Tip by
Highlight • Monument
Tip by
Highlight • Bridge
Tip by
Sign up for free to discover even more attractions around Old Bennington.
Sign up for free
Already have an account?
Start today with a free account
Your next adventure awaits.
Login or Signup
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.
0
0
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.
0
0
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.
0
0
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.
0
0
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.
1
0
Wonderful view from the monument into the distance.
0
0
come between 10 and 5 to see the top of the monument.
1
0
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.
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.
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.
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.
Yes, the Bennington Battle Monument is noted as wheelchair accessible, allowing visitors to experience its historical significance and panoramic views.
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.
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.
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.
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.
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.
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.


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