The main house was built shortly after the Revolutionary War, about 1786, and was a small one-room cape style house built by Colonel Joseph Curtis. Curtis, veteran of the Revolutionary War, arrived in South Egremont, which was really just a patch of woods at that time, on horseback with wife, Rebekah, and son, Jasper, in 1780 from Newington, CT. Joseph was a 22-year old yeoman and young father with not much more than a pension from serving in the Revolutionary War, but he purchased a large tract of farmland in what is today the Village of South Egremont. 

Over 30 years, Colonel Curtis successfully built up the area selling plots of his land to newcomers. He was instrumental in petitioning the state to create two major roadways which are now Routes 23 and 71 through Egremont. The intersection was for many years identified on maps as ‘Curtis Corners’. At the time of his death in 1810, the Curtis homestead sat on 150 acres of farmland.  Col. Curtis was a rich man, known and respected as a Gentleman and Esquire. 

By 1823, son Wilber Curtis was a father of five, and a prominent citizen in his own right. The Honorable Wilber Curtis was a Member of both branches of the Massachusetts Legislature, a Magistrate in Egremont, a trustee and founder of the Egremont Academy (today The Academy Building), the first president of the National Mahaiwe Bank and a delegate to the Constitutional Convention of 1853. Wilber Curtis added a Greek Revival addition to the house which included a more formal front door, two major parlor rooms downstairs, and two additional bedrooms upstairs. He also converted the original part of the house into the kitchen. 

In 1848, in a move that relocated his family to a larger and more prestigious house in N. Egremont, Wilber Curtis sold his personal homestead to Joseph Benjamin, a successful local businessman descended from a family with a century-long history in Egremont. At the time of the purchase, Joseph A. Benjamin owned the Mt. Everett Flouring Mill (today’s Old Mill restaurant), which was built by his father Nathan, and the Egremont Town Store. In 1876, he officially renamed the house “Twin Pines” for the large pines that face Route 23. The house remained in the Benjamin family until 1892.

Throughout the 20th century, different homeowners have added additions to the house, the most recent in 1999. The original beehive oven used for cooking and heating the house can be seen here in the living room of The Egremont Village Inn. The house was first known to be a guest house in the 1940s, and has operated under various names, including the Red Saber Inn, The McMeekin House and the Weathervane Inn. The rooms now hold the style of the days gone by and are all unique.

Today, the Inn still evolves—now with a fresh new look and feel that blends rustic charm with modern touches. Thoughtful updates bring more attention to detail, hospitality, and guest comfort. From the furnishings to the finishes, the vibe is friendly and inviting, while still honoring the history that makes this place special.