A little late to this party (as usual). I have a family member with a house in the Berkshires that he allows me to borrow for a few days each summer. (He is not frum, I am, so it's nowhere near Jiminy Peak). There are always a lot of fun things to do in the area.
Aside from Jiminy Peak, here are a couple of other ideas:
- Ashuwillticook Rail Trail - this is a lakeside walking/running/biking trail along the Cheshire Resevoir in Lanesbourough. You will have to bring your own bikes to ride it - but there are bike shops in the area that might rent them. The whole trail is 12 miles, but atthe moment they are redoing 6 miles of it. We brought our bikes and had a nice ride -
https://www.mass.gov/locations/ashuwillticook-rail-trail- Pleasant Valley Wildlife Sanctuary -
https://www.massaudubon.org/get-outdoors/wildlife-sanctuaries/pleasant-valley another nice set of hiking trails from easy to hard - they also have live beavers living in the sanctuary - $5/person. In Lenox
- The Worthington Golf Club -
https://worthingtongolfclub.com/ - a small executive course in Worthington. It cost about $105 for the 4 of us to play, which included loaner clubs and golf carts. This is slightly more challenging than a pitch and putt course, but manageable if you are a beginner. This is about 30-45 min from central Pittsfield, add 10-15 more from Jiminy Peak
- Lee Premium Outlets -
https://www.premiumoutlets.com/outlet/lee - a very small outlet mall.
- The Basketball Hall of fame is an hour away in Springfield mass
- Clapp Park in Pittsfield has some really nice playgrounds for kids - it's on Housatonic Street
In non-corona years, we've also gone to Bousqet - a ski resort near the pittsfield airport - they have a small water park in the in the summer with 3-4 water slides (and a smaller set for little kids). They went out of business because of corona, and are not open this season, but they have new owners, so we'll see where it goes.(not tznius friendly)
When my kids we're younger we went to Ioka Valley Farm which has farm themed rides and a petting zoo - right near JP
We also went to the Berkshire Museum in Pittsfield, which had some nice exhibits for kids as well - it's currently under renovation