Best attractions and places to see around South Shaftsbury include a mix of historic landmarks, natural features, and cultural sites. This Vermont region is characterized by its scenic landscapes, including parts of the Green Mountain National Forest, and its rich history, evident in its preserved 18th and 19th-century structures. Visitors can explore a variety of outdoor activities and historical points of interest.
Last updated: April 30, 2026
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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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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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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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The area is rich in history. You can visit the Silk Covered Bridge, a historic Town lattice truss bridge built in 1840 and listed on the National Register of Historic Places. Another significant site is the Bennington Battle Monument, commemorating a pivotal Revolutionary War victory. Additionally, the Robert Frost Stone House Museum, where the poet lived and wrote, offers a glimpse into literary history, and the Center Shaftsbury Historic District showcases buildings from before 1880.
Yes, South Shaftsbury offers several natural attractions and scenic spots. Harmon Hill provides fantastic views of Bennington and the surrounding area, with its unique landscape of large green ferns. Lake Shaftsbury State Park is a central natural attraction, featuring the 26-acre Lake Shaftsbury, ideal for swimming and picnicking. A significant portion of the Green Mountain National Forest also lies to the east, offering vast wildlands and trails.
The region around South Shaftsbury is excellent for outdoor activities. You can find numerous hiking trails, including the scenic Carriage Road (Grove Road) within the Mile-Around-Woods area, which is particularly stunning in the fall. There are also running routes and road cycling routes that explore the beautiful country roads and historic sites.
Absolutely. Many attractions are suitable for families. Lake Shaftsbury State Park offers swimming, boat rentals, and a play area. The Silk Covered Bridge and the Bennington Battle Monument are historical sites that can engage children. The Carriage Road (Grove Road) provides an easy and scenic walk for all ages.
The best time to visit largely depends on your preferred activities. Spring and summer are ideal for hiking, swimming, and enjoying Lake Shaftsbury State Park. Fall is particularly popular for its stunning foliage, making scenic drives and walks like the Carriage Road exceptionally beautiful. Winter offers opportunities for snow-related activities, though some attractions may have limited access.
The Bennington Battle Monument is noted as wheelchair accessible. Within Lake Shaftsbury State Park, the Healing Springs Trail includes an accessible boardwalk section, providing an opportunity to experience the diverse natural landscapes.
Beyond the Robert Frost Stone House Museum, you can visit the Shaftsbury Historical Society Museum, housed in what was once Vermont's oldest Baptist Church. This museum offers deep insights into the town's rich history and heritage.
Many outdoor areas in Vermont are dog-friendly, especially trails within the Green Mountain National Forest. It's always best to check specific park or museum regulations before visiting, but generally, trails like the Carriage Road and those leading to Harmon Hill are popular with dog owners. Please ensure your dog is on a leash and you clean up after them.
Visitors frequently appreciate the blend of historical significance and natural beauty. The scenic views from places like Harmon Hill and the historical charm of sites like the Silk Covered Bridge are often highlighted. The peaceful atmosphere of trails such as the Carriage Road, especially during fall foliage, also receives high praise.
While not strictly 'hidden,' the Wooden Footbridge near VT-9 on the Long/Appalachian Trail offers a charming, tranquil spot for a break and photos. The Linda Tilgner Memorial Nature Trail within Howard Park is another peaceful green space offering mountain views, often less crowded than major attractions.
Hiking trails in the area offer varied terrain. You'll find easy, relatively flat paths like the Healing Springs Trail boardwalk and sections of the Carriage Road. More moderate trails, such as those leading to Harmon Hill, involve some elevation gain and can traverse forested areas, streams, and open fern-covered summits.


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