32 days in Stockbridge, West Stockbridge & Lenox Itinerary

32 days in Stockbridge, West Stockbridge & Lenox Itinerary

Created using Inspirock Berkshires trip maker

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Stockbridge
— 15 nights
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West Stockbridge
— 6 nights
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Lenox
— 10 nights
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Stockbridge

— 15 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Let the collections at Norman Rockwell Museum and Storm King Art Center capture your imagination. Get a sense of the local culture at Gillette Castle State Park and Bidwell House Museum. Explore Stockbridge's surroundings by going to Priam Vineyards (in Colchester), New Paltz (DM Weil Gallery & Dressel Farms) and Minnewaska State Park Preserve (in Kerhonkson). And it doesn't end there: steep yourself in history at Chesterwood Museum, immerse yourself in nature at Haystack Mountain State Park, delve into the lush surroundings at Topsmead State Forest, and walk around Skinner State Park.

To see other places to visit, where to stay, traveler tips, and other tourist information, use the Stockbridge trip website.

Boston to Stockbridge is an approximately 2.5-hour car ride. You can also take a bus; or take a train. Plan for slightly colder nights when traveling from Boston in June since evenings lows in Stockbridge dip to 53°F. Wrap up your sightseeing on the 1st (Sun) early enough to travel to West Stockbridge.

Things to do in Stockbridge

Parks · Nature · Outdoors · Historic Sites

Side Trips

West Stockbridge

— 6 nights
West Stockbridge is a town in Berkshire County, Massachusetts, United States. Do some cultural sightseeing at Franklin D. Roosevelt Presidential Library and Museum and Eleanor Roosevelt National Historic Site. Popular historic sites such as Home of Franklin D. Roosevelt and Olana State Historic Site are in your itinerary. Venture out of the city with trips to Overlook Mountain (in Woodstock), Vanderbilt Mansion National Historic Site (in Hyde Park) and Windham Mountain (in Windham). And it doesn't end there: Head underground at Howe Caverns, make a trip to Turn Park Art Space, relax in the rural setting at Sprout Creek Farm, and snap pictures at Walkway Over the Hudson State Historic Park.

To see maps, more things to do, and other tourist information, you can read our West Stockbridge day trip planning website.

West Stockbridge is very close to Stockbridge. In July, plan for daily highs up to 79°F, and evening lows to 59°F. Cap off your sightseeing on the 7th (Sat) early enough to travel to Lenox.

Things to do in West Stockbridge

Historic Sites · Parks · Winter Sports · Outdoors

Side Trips

Lenox

— 10 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Escape the urban bustle at Zipline and Mount Greylock. Let the collections at The Mount, Edith Wharton's Home and Hancock Shaker Village capture your imagination. Explore Lenox's surroundings by going to North Adams (Natural Bridge State Park & MASS MoCA), The Clark Art Institute (in Williamstown) and Mount Greylock State Reservation (in Lanesboro). The adventure continues: explore the galleries of Hildene, The Lincoln Family Home, stop by Concepts of Art Lenox Judaica, identify plant and animal life at Arcadia Wildlife Sanctuary, and take in the awesome beauty at Equinox Mountain.

To find reviews, other places to visit, and more tourist information, go to the Lenox online trip planner.

Lenox is just a short distance from West Stockbridge. In July, daytime highs in Lenox are 79°F, while nighttime lows are 59°F. Finish your sightseeing early on the 17th (Tue) so you can drive back home.

Things to do in Lenox

Parks · Nature · Museums · Historic Sites

Side Trips