Camping
- Camp at Spacious Skies Woodland Hills Campground in Austerlitz, NY. Located right over the Mass line into NY. Nice small campground to relax at and use as a launch for nearby activities. https://spaciousskiescampgrounds.com/woodland-hills/?utm_source=google&utm_medium=organic&utm_campaign=WH_GMB_2025&utm_id=GMB.2025
Stockbridge, MA
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Norman Rockwell Museum in Stockbridge, MA – https://www.nrm.org
- Kayak Stockbridge Bowl in Stockbridge, MA https://massachusettspaddler.com/stockbridge-bowl-berkshire Great place to paddle. Nice, clear lake, beautiful homes to gawk at from the water, big boat ramp parking lot, port-a-potty on site. There are power boats, sail boats, but they are respectful of paddlers. Paddle along the shore and enjoy the views. Approximately 3 miles around the edge of the lake.
- Walk Main Street in Stockbridge and window shop through the interesting shops and restaurants
- Wine Tasting? Furnace Brook Winery at the Hilltop Orchards in Richmond, MA – Just west of Stockbridge, has delicious wines, hard ciders, homemade apple cider donuts, and other snacks. In winter, a big fireplace is nice to sit in front of and enjoy the warmth. Hiking and x-country trails, full moon hikes, and more. https://www.hilltoporchards.com
Lenox, MA
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Tanglewood in Lenox, MA – Summer home of the Boston Symphony Orchestra https://www.bso.org. Great performances on the lawn. Bring chairs, a meal, a bottle of wine, and relax to wonderful music
- The Mount, Edith Wharton’s Home in Lenox, interesting home to tour. Visit the pet cemetery. Night haunted tours are given too and are
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Chesterwood – https://www.chesterwood.org – creator of the Lincoln Memorial and many other sculptures.
Great Barrington, MA
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Burgers and brews, the Barrington Brewery in Great Barrington is a tasty spot for lunch or dinner – http://www.barringtonbrewery.net. Located on Rt 7 on the way into Great Barrington
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Bash Bish Falls – short hike to a small and pretty waterfall. https://www.mass.gov/locations/bash-bish-falls-state-park
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Walk Main Street in Great Barrington. Interesting stores and restaurants. Great ice cream at the Barrington Creamery.
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Monument Mountain reservation in Great Barrington – nice views at the top http://www.thetrustees.org/assets/documents/places-to-visit/trailmaps/Monument-Mountain-Trail-Map.pdf
- Located West of Great Barrington is the Catamount Aerial Adventure – ropes course and zip lining – fun, fun, fun https://www.catamounttrees.com
Pittsfield, MA
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Balderdash Cellars wine tastings – https://balderdashcellars.com
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Kayak at Onota Lake, Pittsfield – bring a picnic and enjoy the surroundings.
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Kayak on Pontoosuc Lake, Pittsfield – visit the island in the middle, park at Pontoosuc Park and put your kayak in there.
North Adams, MA
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Mass MOCA, aka Massachusetts Museum Of Contemporary Art, in North Adams. This place is BIG. Lots to see. massmoca.org
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Museum of Dog in North Adams. Do this and Mass MOCA on the same trip. Small museum dedicated to everything dog. http://www.museumofdog.com/
Williamsburg, MA
- The Clark is a vast art museum located in the beautiful Berkshires. The museum is known worldwide and is a must-stop for art lovers. https://www.clarkart.edu/