Discover trusted tour operators offering experiences in The Berkshires. Browse operators, compare tours, and book instantly with free cancellation.

Discover top-rated tours and experiences from trusted operators in The Berkshires. Book instantly with free cancellation.
Experience world-class performing arts and stunning natural beauty in The Berkshires.
Discover charming New England towns nestled amidst rolling hills and picturesque landscapes.
Enjoy farm-to-table dining and artisanal shops showcasing local craftsmanship.
Explore a rich history of artists and writers who found inspiration here.
Immerse yourself in a vibrant community known for its welcoming atmosphere.
Escape to a serene countryside offering both cultural richness and outdoor adventure.
While The Berkshires is spread out, getting around is manageable. A car is highly recommended for exploring its charming towns and scenic routes. Public transportation is limited, with regional bus services connecting some larger towns. Ride-sharing services are available in certain areas, but can be less reliable in more rural spots. Consider renting a car upon arrival or factoring in taxi services for specific excursions to fully enjoy getting around The Berkshires at your own pace. Check local shuttle services for specific attractions like Tanglewood during peak season.
Prefer renting a car? See options here.
Browse trusted tour operators offering experiences in The Berkshires. Click any operator to view their tours.
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Explore comprehensive guides to plan your perfect trip, including food tours, cultural experiences, and more.
Explore the vibrant artistic heart of the Berkshires through curated gallery walks and intimate studio visits, connecting you with local creators and their inspiring works.
Discover the authentic flavors of The Berkshires with immersive farm visits and delicious culinary explorations.
Discover guided hikes and nature walks across the stunning landscapes of the Berkshires, from rolling hills to serene lakes.
Step back in time with immersive tours exploring the preserved charm of The Berkshires' historic villages and the unique legacy of Shaker life.
Discover the landscapes and homes that inspired some of America's most cherished writers on engaging literary tours in The Berkshires.
Immerse yourself in the vibrant cultural landscape of The Berkshires with curated tours showcasing world-class music, theater, and artistic heritage.