TOP 30 Best guided tours in Stockbridge, Massachusetts

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Housatonic Flats Reserve is a beautiful park located at 439 Stockbridge Road in Great Barrington, Massachusetts, United States. This serene reserve offers visitors a peaceful escape into nature, with lush greenery, meandering trails, and stunning views of the Housatonic River. Perfect for a leisurely stroll, birdwatching, or simply relaxing in the great outdoors, Housatonic Flats Reserve is a hidden gem waiting to be explored. Whether you're looking for a quiet retreat or a place to reconnect with nature, this park is the perfect destination for nature lovers of all ages.

Taggart House is a unique institution located at 18 Main Street in the charming town of Stockbridge, Massachusetts. As a health center, Taggart House offers a range of services aimed at promoting wellness and holistic healing. Whether you're looking for acupuncture, massage therapy, or nutritional counseling, their team of experienced professionals is dedicated to helping you achieve optimal health. In addition to their health services, Taggart House also operates as a real estate agency, assisting clients in finding their dream home in the picturesque Berkshires region. With a deep knowledge of the local market and a commitment to personalized service, their team can help you navigate the real estate process with ease.

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 Naumkeag, a stunning museum, park, and tourist attraction nestled in the heart of Stockbridge, Massachusetts. Located at 5 Prospect Hill Road, this exquisite 48-acre estate offers a glimpse into the grandeur of the Gilded Age, featuring breathtaking gardens and a rare Berkshire "cottage" that was once the summer retreat of the Choate family. Designed in 1884 by the renowned architectural firm McKim, Mead & White, Naumkeag is a remarkable example of shingle-style architecture with 44 rooms that served as a family home for several generations. Visitors can explore the meticulously maintained landscapes, including 8 acres of formal gardens, meadows, and farmland, which provide a serene escape and a chance to step back in time. Please note that due to the estate's age and terrain, it is not wheelchair- or stroller-accessible.

Welcome to the Mission House, a National Historic Landmark nestled in the heart of Stockbridge, Massachusetts. Located at 19 Main Street, our museum and garden offer an immersive journey through time, unraveling the rich tapestry of the Stockbridge Mohicans and the legacy of missionary John Sergeant. Built around 1742 by John Sergeant, the Mission House has stood as a silent witness to the evolution of Stockbridge for nearly two centuries. Originally constructed to aid Sergeant in his mission to assimilate the Mohican people, this Colonial-era house was later preserved by Mabel Choate, who relocated it to its current location. Choate enriched the property with her collection of colonial American furnishings and established a museum featuring Mohican artifacts.

Welcome to The Trustees of Reservations, a haven for nature lovers and history enthusiasts alike, located at 1 Sergeant Street, Stockbridge, Massachusetts. As a distinguished museum and tourist attraction, we are dedicated to preserving the exceptional scenic, historic, and ecological treasures of Massachusetts. Our mission is to protect the places you love for their trails, history, gardens, and beaches, recognizing that nature and culture enrich our lives and soothe the soul. Explore the beauty of Massachusetts through our diverse offerings, from historic estates to breathtaking natural landscapes. Immerse yourself in our scenic trails, picturesque gardens, and serene beaches that promise a rejuvenating experience. For those interested in history, delve into the rich past of the region with guided tours and educational programs.