A statue of General John Stark at the Bennington Battle Monument.
A statue of Brigadier General John Stark at the Bennington Battle Monument.

While located entirely in the town of Bennington, a visit to Old Bennington, Vermont is a bit like stepping back in time. This historic village is home to less than 200 people, along with beautiful historic buildings, and a most colorful past. 

Whether you’ve lived in the area for years or are visiting for the first time, there’s a lot to discover on an Old Bennington walking tour. Here are some of our favorite things to see and do in Old Bennington, Vermont.

First Stop, the Bennington Museum

The Bennington Museum in Bennington, Vermont
Be sure to make time to explore the Bennington Museum!

The renowned Bennington Museum is a great place to begin your tour. A stop in the Military Gallery will give you an overview of the Batlle of Bennington and Bennington’s Revolutionary War history, complete with an exhibit of Vermont-made firearms.

Other historical gems include one of the oldest American flags in existence, a Martin Wasp automobile, which was made in Bennington in 1925, and the largest collection of Grandma Moses paintings in the world.

In addition to the Bennington Museum’s permanent history and art collections, temporary exhibitions delve deep into the art, history, and innovation of the Green Mountain State. 

Current and Exhibitions at the Bennington Museum

  • Fields of Change: 1960s Vermont: June 29 through November 3 – Bennington Museum’s major exhibition for 2019,  Fields of Change: 1960s Vermont explores a complex time that in many ways has come to define Vermont as it is today more than any other moment in history. The exhibition explores this iconic time period through photographs, archival documents, works of art, posters, fashion, hand-made craft objects, and more.
  • Visible in Vermont: Our Stories, Our Voices: September 14 –  December 30 – A multi-generational photo and story exhibition that highlights self-identified people of color living and/or going to school in Vermont.
  • Asa Cheffetz: Vermont Wood Engravings: September 21 –  December 30 – The wood engravings of Asa Cheffetz served as printing plates that created many intricate, yet simple prints produced in the 1930s and 40s. The engravings were inspired by the Vermont countryside and portray the artist’s strong love of the land.
  • Color Fields: 1960s Bennington Modernism: June 29 through December 30 – During the 1960s, Bennington College served as a rural epicenter for a group of artists who were pushing the possibilities of abstraction in pared-down, color-based works that have come to be known collectively as Color Field. This exhibition looks at this critical moment when artists connected to Bennington led the way in American art.

Visiting the Old First Church and the Bennington Center Cemetery

The Old First Church in Bennington, Vermont.
The cemetery behind the Old First Church

The Old First Church was built in 1805 and represents the first church in Vermont to reflect the separation between church and state. Before 1805, the Protestant congregation, which was “gathered” in 1762, met in a simple pine meetinghouse in the center of the village, not far from where the current church stands today.

The cost to build the “new” Old First Church was $7,793.20. Money was raised by selling box pews on the first floor to parishioners for anywhere from $40 to $500 each. The upper pews were called the Free Gallery, with seating for children and visitors. 

Behind the Old First Church is the Bennington Center Cemetery, one of the oldest cemeteries in Vermont. Robert Frost, Vermont’s most famous poet, is buried here, along with his family. You will also find the graves of three former governors, many Revolutionary War soldiers who died during the Battle of Bennington, and even a Loyalist who was executed in Bennington in 1778. The oldest gravestone is that of Bridget Harwood, who died in 1762.

Many of the gravestones provide excellent examples of historic death imagery, including winged skulls and cherubs that were popular during the late 1700s, as well as some highly decorative floral motifs.

Stroll up Historic Monument Avenue

A historic home in Old Bennington, Vermont.
Just one of the many historic homes on Monument Avenue in Old Bennington.

After leaving the Old First Church and cemetery, head up the hill toward the Bennington Monument. Monument Avenue includes many large historic homes dating to the late 1700s. For a more detailed account of the styles, dates, and former residents of these homes, visit the Town of Bennington website.

As you walk up Monument Avenue, you will discover a larger-than-life copper catamount marking the spot of the former Catamount Tavern. The tavern served as the headquarters of Ethan Allen and the Green Mountain Boys, and later the headquarters of General Stark who commanded the forces in the Battle of Bennington. 

A statue of a catamount commemorating the famous Catamount Tavern in Old Bennington, Vermont.
The site of the famous Catamount Tavern.

The tavern was originally known as Fay’s House, but when residents placed a real stuffed catamount on the signpost to threaten unwelcome New Yorkers, the name was changed to the Catamount Tavern. The tavern was built in 1769 but burned to the ground in 1871.

Other notable buildings on Monument Avenue, include the Old Academy, built originally as a school in 1819, and the Fay-Brown house, which was a stone blacksmith shop constructed in 1781. 

The Bennington Battle Monument

The Bennington Battle Monument in Old Bennington, Vermont.
The Bennington Battle Monument in Old Bennington.

Towering above the town of Bennington at 306 feet and 4 and ½ inches tall, the Bennington Battle Monument is the tallest building in Vermont and the third-tallest battle monument in the world. It commemorates the famous Battle of Bennington, fought in nearby Walloomsac, New York in 1777. 

British forces, along with Indians, Loyalists, and German mercenaries of approximately 700 soldiers were in need of military stores and supplies and heading for the arsenal depot located at the current site of the Bennington Monument. The first shots were fired at 3 pm on August 16, and the British were defeated by General John Stark, his army of 2,000 volunteers, and Colonial Seth Warner with the Green Mountain Boys. The Battle of Bennington paved the way for another British defeat in Saratoga, which was a major turning point in the American Revolution.

An informational sign for the Bennington Battle Monument in Bennington, Vermont.

The idea of a monument to commemorate the battle began in the early 1800s but wasn’t realized for many decades. The five-ton cornerstone for the Bennington Battle Monument was placed on August 16, 1887. The Monument was constructed with Sandy Hill Dolomite, quarried in Hudson Falls, New York, and brought to Bennington on a railroad track built specifically to transport stone for the building. 

The capstone was placed on November 25, 1889, and the building was dedicated in 1891.

Visitors can take the elevator up to the observation tower at 188 feet for a fabulous view of Vermont, New York, and Massachusetts. See if you can spot ammonite fossils embedded in the dolomite on the outside of the Monument.

The Bennington Battle Monument is Vermont’s most popular state historic site and is open for tours between May 1 and October 31 from 10 am to 5 pm. The grounds are also a great spot for an afternoon picnic.