Best Attractions near Chesterwood

Experience the vibrant community spirit at Guthrie Center in Great Barrington, MA, where live music and local art create an unforgettable atmosphere.

Explore the scenic beauty and outdoor adventures at Fountain Pond State Park, a perfect getaway in Great Barrington, Massachusetts.

Discover the historic charm of The Playhouse in Lee, Massachusetts, a cultural gem nestled in the picturesque Berkshire Mountains.

Experience the stunning views and serene beauty of Olivia's Overlook on Yokun Ridge, a top destination for nature lovers in the Berkshires.

Discover the literary legacy of Edith Wharton at The Mount, a historic estate in the scenic Berkshire Hills, combining breathtaking gardens with rich cultural offerings.

Explore the artistic legacy of George Morris and Suzy Frelinghuysen at this charming museum in Lenox, Massachusetts, set against the backdrop of the beautiful Berkshires.

Discover the beauty of Alford Springs Reserve, a top hiking and nature preserve in Great Barrington, MA, offering stunning views and serene trails.

Explore the captivating Asian art and antiques at AsiaBarong Gallery in Great Barrington, where cultural heritage meets artistic expression.

Experience the enchanting blend of music and nature at Tanglewood, a premier tourist attraction in Lenox, Massachusetts.

Discover the opulence of the Gilded Age at Ventfort Hall, a historic mansion and museum offering rich insights into America's luxurious past.

Discover the serene beauty of Benedict Pond Loop in Great Barrington, MA - a perfect hiking destination for nature lovers and families.

Explore the natural beauty of Kennedy Park in Lenox, MA - a scenic park perfect for hiking, picnicking, and enjoying the great outdoors.

Discover October Mountain State Forest: A captivating blend of nature, adventure, and tranquility in the heart of the Berkshires.

Explore the fascinating history of railroads at the Berkshire Scenic Railway Museum, where vintage trains and scenic rides await in Lenox, Massachusetts.

Experience the thrill of winter sports at Butternut Ski Area, a family-friendly ski resort in the stunning Berkshire Mountains of Massachusetts.

Explore the serene landscapes and diverse wildlife at Mass Audubon's Pleasant Valley Wildlife Sanctuary, a true haven for nature lovers in Lenox, Massachusetts.

Discover the breathtaking trails and serene landscapes of Tyringham Cobble Park, a must-visit destination in the Berkshires for nature enthusiasts.

Experience the breathtaking beauty and outdoor adventures at Beartown State Forest, a natural gem in Massachusetts perfect for hiking, fishing, and wildlife viewing.

Explore the Bidwell House Museum in Monterey, MA - a historical treasure showcasing early American life amidst stunning natural beauty.

Experience the beauty and flavor of Balderdash Cellars, a picturesque winery in Richmond, Massachusetts, perfect for wine lovers and foodies alike.

Discover the charming Welcome to The Berkshires Sign, your gateway to a region filled with natural beauty, cultural experiences, and outdoor adventures in Massachusetts.

Discover the serene hiking trails of Mahanna Cobble Reserve in Pittsfield, MA, where nature meets tranquility and adventure awaits.

Explore the historic Hancock Shaker Village, a living museum showcasing Shaker culture, architecture, and the beauty of communal living in Massachusetts.

Explore Ashintully Gardens, a serene oasis in Tyringham, MA, where nature's beauty flourishes and tranquility awaits.

Explore the excitement of Catamount Aerial Adventure Park, where thrilling aerial courses meet breathtaking views in the heart of Massachusetts.

Discover the life and works of Herman Melville at Arrowhead, his historic home and a key landmark in American literary history.

Discover the natural beauty and tranquility of Barkerville Conservation Area, a perfect destination for outdoor activities and family outings in Pittsfield, Massachusetts.

Explore the mysteries of Thom Reed - UFO Monument Park in Sheffield, Massachusetts, where history and the unknown intertwine in a serene natural setting.

Capture the essence of Massachusetts with the iconic Welcome to MASSACHUSETTS signage in Pittsfield, a perfect photo opportunity for every traveler.

Experience the tranquility of nature at Mass Audubon Canoe Meadows Wildlife Sanctuary, a paradise for birdwatching and hiking enthusiasts in Massachusetts.

Discover the natural beauty of Bob's Way in Monterey, MA – a serene hiking trail with breathtaking views and diverse wildlife.

Explore the captivating ruins and serene landscapes of Questing, a nature preserve and tourist attraction in New Marlborough, Massachusetts.

Explore the breathtaking trails and serene landscapes of Berkshire Knapsackers, a premier hiking destination in Pittsfield, Massachusetts.

Experience the tranquility of Kirvin Park in Pittsfield, MA, where nature and recreation come together for a perfect day outdoors.

Explore art, history, and natural science at the Berkshire Museum in Pittsfield, MA—a cultural treasure for every traveler.

Explore The Common in Pittsfield, a beautiful park offering a serene escape and a glimpse into local culture amidst stunning natural beauty.

Experience the tranquility of Burbank Park, a beautiful green oasis in Pittsfield, Massachusetts, perfect for relaxation and outdoor activities.

Explore the breathtaking trails and scenic vistas of Mount Everett State Reservation, a nature lover's paradise in the heart of Massachusetts.

Explore the breathtaking trails of Lower Carroll Mill Trailhead in New Marlborough, Massachusetts, a haven for hiking enthusiasts and nature lovers.

Experience the tranquil beauty of Ray Crow Park in Pittsfield, MA, where nature and relaxation meet in a serene city park setting.

Explore the natural beauty and recreational offerings of Springside Park in Pittsfield, Massachusetts - a perfect outdoor escape for visitors.

Experience the breathtaking beauty of Bash Bish Falls State Park, where cascading waterfalls and scenic trails await your adventure in Massachusetts.

Discover the breathtaking Umpachene Falls Park in Southfield, MA, where tiered waterfalls meet serene trails for an unforgettable outdoor experience.

Discover the beauty and history at Becket Land Trust & Historic, a unique blend of art, culture, and nature in the heart of Massachusetts.