The Best Historical site tours in Sheffield, Massachusetts

Welcome to the Shay's Rebellion Battle Site Monument, a significant historical landmark nestled in the picturesque town of Great Barrington, Massachusetts. Located on Sheffield-Egremont Road, this monument commemorates the pivotal events of Shay's Rebellion, a crucial uprising in the late 18th century that helped shape the course of American history. Visitors to the Shay's Rebellion Battle Site Monument will find themselves immersed in the rich history of early America. The site offers a serene and reflective setting where you can explore the origins and impact of the rebellion led by Daniel Shays and other Revolutionary War veterans, who stood against economic injustices and government policies of the time.

Welcome to Ashley House, a captivating museum and tourist attraction located at 117 Cooper Hill Road, Sheffield, Massachusetts. Nestled in the picturesque Berkshires, this historic site offers a profound journey through time, exploring the narratives of two influential figures who fought for freedom and liberty, forever altering the course of our region’s history. The Colonel John Ashley House, a cornerstone of the Upper Housatonic Valley African American Heritage Trail, stands as one of the earliest European-style dwellings in the Berkshires. Built in 1735, this remarkable Colonial-era house was once the epicenter of white political and social life in colonial Sheffield. Colonel John Ashley, a prominent and wealthy figure, owned vast lands and businesses, prospering significantly from the institution of slavery.