Southwest Vermont Fall Foliage Scenic Drive

Southern Vermont is home to many beautiful locations which are must-see spots in the fall. While every year is different, Vermont reliably sees its best fall colors, moving from north to south, starting in mid-to-late September and extending through mid-October. This blog post features some of the best fall foliage locations in Southern Vermont along with a road trip map. Just driving alone Route 7A is a great experience within itself!

Stop #1

“Old First” Congregational Church

Town: Bennington, Vermont

Location: HERE

The Old First Church, also known as the First Congregational Church of Bennington, is a historic church in Old Bennington, Vermont. The congregation was founded in 1762, and the current meeting house was constructed in 1805. In 1973, the building was listed on the National Register of Historic Places as one of the best examples of Federal period religious architecture in the state. The church really shines when it is surrounding by lovely fall colored trees!

Stop #2

Bennington Battle Monument

Town: Bennington, Vermont

Location: HERE

The Bennington Battle Monument stands 306 feet 4 1/2 inches tall and was dedicated in 1891. It is made of blue-grey magnesian limestone.

The Monument was erected to commemorate the Battle of Bennington, which took place on August 16, 1777, and is regarded as a watershed moment in the Revolutionary War. The State of Vermont owns it, and The Friends of the Monument, a non-profit volunteer group, supports it. Every year, the Monument hosts a number of events that are open to the public.

Stop #3

Silk Road Covered Bridge

Town: Bennington, Vermont

Location: HERE

The Silk Covered Bridge spans the Walloomsac River between downtown Bennington, Vermont and the village of North Bennington, Vermont. It was built in 1840 as a Town lattice truss bridge style and is one of three covered bridges across the river in close proximity.

Stop #4

Paper Mill Village Bridge

Town: Bennington, Vermont

Location: HERE

The Paper Mill Village Bridge, also known as the Paper Mill Bridge or the Bennington Falls Covered Bridge, is a wooden covered bridge that spans the Walloomsac River northwest of Bennington, Vermont. It was built in 1889 and is 125 feet long. It was added to the National Register of Historic Places in 1973.

Stop #5

Henry Covered Bridge

Town: North Bennington, Vermont

Location: HERE

The Burt Henry Covered Bridge, also known as the Henry Covered Bridge or simply the Henry Bridge, spans the Walloomsac River near Bennington, Vermont. It is a Town lattice truss bridge that spans River Road just south of North Bennington. It was listed on the National Register of Historic Places in 1973 as Bennington County’s oldest covered bridge, having been built around 1840. The Vermont Agency of Transportation rebuilt it in 1989. It has a length of 121 feet.

Stop #6

The Mile-Around Woods

Town: North Bennington, Vermont

Location: HERE

Ethel McCullough Scott and her husband Bill Scott donated the Mile-Around Woods to The Fund for North Bennington in 1994. Mrs. Scott’s family had owned the property for over 200 years. Trenor Park, the builder of the nearby Park-McCullough House, laid out a circular carriage road in the Woods after the Civil War. It is an excellent location for viewing the stunning fall foliage of Southern Vermont.

Stop #7

Robert Frost Stone House Museum at Bennington College

Town: Shaftsbury, Vermont

Location: HERE

The Robert Frost Stone House Museum is a literary landmark in Old Bennington, Vermont, just minutes away from Frost’s gravesite. Frost lived in the house from 1920 to 1929, during which time he wrote many of the pieces that became part of his first Pulitzer Prize-winning collection, New Hampshire, which included “Stopping by Woods on a Snowy Evening.” Frost wrote the poem at the dining room table on a hot June morning in 1922. This American classic has taken over the entire room.

Even before the Frost era, the house, which was built around 1769, was considered historic. It’s a rare example of Dutch Colonial architecture made of native stone and timber that hasn’t changed much since Frost’s time. Frost’s original apple trees can still be found on the seven-acre property.

Stop #8

Arlington Covered Bridge

Town: Arlington, Vermont

Location: HERE

The Arlington Green Covered Bridge is a covered bridge in Arlington, Vermont, off Vermont Route 313. Covered Bridge Road is crossed by thisTown lattice truss bridge. It is 80 feet long and was built in 1852. In 1973, it was added to the National Register of Historic Places.

Stop #9

Chiselville Covered Bridge

Town: Sunderland, Vermont

Location: HERE

The Chiselville Covered Bridge is a covered bridge in Sunderland, Vermont that spans the Roaring Branch of the Batten Kill. Daniel Oatman built the bridge in 1870. It is a lattice truss bridge with additional steel I-beams added in 1973 to repair damage caused by two overweight gravel trucks in 1971. It was restored and is in operation today.

Stop #10

Mount Equinox Skyline DriveThe Saint Bruno Scenic Viewing Center

Town: Sunderland, Vermont

Location: HERE

Skyline Drive, the longest privately owned, paved toll road in the United States, ascends 3,248 feet over 5.2 miles from historic Route 7A between Manchester and Arlington, Vermont, to the top of Mount Equinox. It has been in continuous operation since its completion in 1947, and it is one of the country’s safest, best-engineered, and most well-built toll roads.

There are several vistas and picnic areas along the Drive which allows visitors to take in the stunning fall foliage of Southern Vermont.

Stop #11

Hildene, The Lincoln Family Home

Town: Manchester, Vermont

Location: HERE

Hildene, the Lincoln Family Home, was Robert Todd Lincoln and Mary Harlan Lincoln’s former summer home. Robert Todd Lincoln was the eldest of President Abraham Lincoln and his wife Mary Todd Lincoln’s four sons, and the only one to live to adulthood. He first came to Manchester Center, Vermont, when he was 20 years old, in the summer of 1863, to escape the heat of Washington, DC, and stayed at the nearby Equinox House.

Hildene is derived from the old English words for hill and valley with stream. The house, built in the Georgian Revival style in 1905, sits on a 300-foot promontory overlooking the Battenkill Valley. Approximately half of the 412-acre estate is located at the valley’s lower level and includes meadows and wetlands. In 1907, a formal garden in the shape of a cathedral’s stained glass window was planted. The window pattern is defined by a privet hedge and filled with mixed borders of annual and perennial flowering plants, creating a multicolored “stained glass” effect. The garden is particularly well-known for its collection of over 1,000 herbaceous peonies.

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