The Berkshires Blog

The 18th Century Trail

A guide to six of Berkshire County’s earliest homes

By Chris Hayden

Long before the Mass Pike or Taconic Parkway brought tourists to Berkshire County, there was already a growing interest in the region’s unique environment.  People braved the worst that nature could throw at them while moving steadily away from the burgeoning infrastructure of the colonies – in search of commercial opportunity, religious freedom and social justice.

The Historic Berkshires: An 18th Century Trail offers a guide to six of the earliest homes in Berkshire County, each with a rich history and a unique story to tell. The homes are open to the public for tours and visitors are encouraged to explore how each of these homes occupies a prominent place in Berkshire history.

The oldest home on the trail is The Ashley House in Sheffield, built in 1735. The home was built by Colonel John Ashley, who fought during the Revolutionary War. But it’s not the Ashley family that makes this house unique. A slave who lived at the home interpreted the phrase “all men are created equal” from the Massachusetts Constitution, and believed that this natural right also protected her. And so Elizabeth ‘Mum Bett’ Freeman eventually sued for her freedom in the Massachusetts Court in 1781 and won. This was a significant development, and the first crack in the institution of slavery in the state.

The home is listed on the National Register of Historical Places and has daily house tours along with the exhibit, Elizabeth Freeman: A Story of Courage.

Stockbridge is home to the Mission House. This National Historic Landmark was home to the Reverend John Sergeant, who in the mid-1730s lived as a missionary among the Stockbridge Mohicans. In 1739 he married Abigail Williams and had the Mission House built in 1742 on Prospect Hill. The home stood on the hill until 1926 when it was moved piece by piece to its current location on Main Street in Stockbridge. The house has a small on-site museum, exhibits artifacts from Rev. Sergeant’s time in the home and among the Stockbridge Mohicans and includes some information on the tribe who continues their own tradition from their community in Wisconsin.

Tucked into the woods of Monterey is one of the oldest and finest homes in Berkshire County, the Bidwell House Museum. This Georgian saltbox was originally a parsonage of Reverend Adonijah Bidwell in 1750. Despite several additions and wings throughout the centuries, many of the original features of house are prominent today including four fireplaces, two beehive ovens and a collection of furnishings and decorative arts from the 18th and early 19th century.

Set on 192 acres the museum is able to offer several workshops and other activities in gardens, woodlands and fields.

The Captain Truman Wheeler site in Great Barrington, home of the Great Barrington Historical Society, was built in 1771 – and was just added to the National Register of Historic Places in 2011. Due to the fact that diaries spanning three centuries were found in the house, it is uniquely positioned to provide the most true to form and intimate details of life during the late 18th century into the American Revolutionary period.

A central chimney, wide-pine floors and original blacksmithed metal work are original to colonial times at The Wheeler House.

The only home on the Trail featuring brick (even more uniquely – home-made brick), the Dan Raymond House in Sheffield was built in 1774 by merchant Dan Raymond, who at the time was the fourth largest taxpayer in the town. 

Home of the Sheffield Historical Society, The Dan Raymond House is part of a larger complex of buildings and gives visitors a unique window into Colonial America. Not only was Mr. Raymond wealthy but leading up to the American Revolution he was allied with the Tories. Upon the outbreak of the war though, he became an ardent Patriot.

The northern most home on the 18th Century Trail, in Pittsfield, is Arrowhead. Built in 1790, Arrowhead truly gained its fame in 1850 when Herman and Elizabeth Melville moved to the sprawling farmhouse with immediate and distant family. At the time, Melville was a struggling writer still looking for his niche. Moby Dick was completed in the Pittsfield home and some say it was inspired by the view out of his writing room window which still bears the profile of what could be the white whale. 

The house holds several unique clues to life during the early colonial period. As the home of the Berkshire Historical Society the rooms have been meticulously curated to reflect the inhabitant’s lives. The furniture, garments, chimney (subject of Melville’s poem, I and my Chimney) and barn all reflect the live’s lived here. There are daily tours throughout the summer and self-guided tours of the surrounding grounds. The museum also has rotating exhibits throughout the season.

All of the homes on the trail are open for tours. For more information visit the individual websites, and enjoy the journey though pre-Colonial Berkshire County. It’s one thing to read about it in the history books and another altogether to see how people lived with your own eyes. Don’t miss this amazing opportunity.
Chris Hayden is a communication consultant living in Pittsfield with his wife and two daughters. After working for several New Hampshire newspapers, Mr. Hayden and his wife moved to Berkshire County in 2005 where he started a career in public relations and marketing communication.