The Best Regional trips in Sheffield, Massachusetts

The Race Mountain House is a unique institution located at 894 South Undermountain Road in Sheffield, Massachusetts, United States. As a real estate agency and travel agency, The Race Mountain House specializes in providing exceptional services for those looking to buy or rent properties in the picturesque Berkshires region. Whether you're searching for your dream home or planning a relaxing getaway, our dedicated team is here to assist you every step of the way. Experience the beauty and tranquility of the Berkshires with The Race Mountain House.

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.

Welcome to the Appalachian Trail Access Point in Sheffield, Massachusetts! Nestled in the picturesque landscapes of the Berkshires, our access point provides nature enthusiasts, hikers, and adventurers with a gateway to the world-famous Appalachian Trail. Located in the charming town of Sheffield, MA 01230, our park serves as an ideal starting point for your outdoor excursions. Whether you're planning a day hike, a weekend camping trip, or embarking on the journey of a lifetime along the Appalachian Trail, our access point offers convenient and easy access to one of America's most celebrated long-distance hiking trails. Surrounded by lush forests, rolling hills, and stunning vistas, this location is perfect for those seeking tranquility, natural beauty, and a connection with nature.