Some fun things to do:
~ bike ride the Ashuwillticook Rail Trail (rent bikes at Berkshire Outfitters, which is 1/4 mile off the rail trail; south of Adams); extremely smooth pavement and great for in-line skates too. One section along lakeshore is exceptionally scenic for a rail trail
~ Rafting the Deerfield River (
www.zoaroutdoor.com is generally considered the premier outfitter here)
~ Spas in-and-around Lenox
~ ATVing in Pittsfield State Forest
~ great waterfalls (March Cataract Falls, The Cascade, Tannery Falls, Twin Cascade, Wahconah Falls, Money Brook Falls, Peck's Falls, Bash Bish Falls, Race Brook Falls)
~ swimming holes (Bellevue Falls)
~ Mass MOCA museum
~ Shopping at Lee Outlets (if you want a break from the outdoors)
~ Nice restaurants and great brewery in Great Barrington
~ drive or hike to summit of Mt. Greylock; climb the tower on top
~ hike Monument Mtn in Great Barrington
~ Norman Rockwell Museum
~ Hancock Shaker Village
~ Bubs BBQ in Sunderland (I am not affiliated with them, but I think they have the best baby back ribs in New England)
~ picnic/concert at Tanglewood. Simon & Garfunkel are playing at the end of the July.
~ canoeing the Hoosatonic River from Lenox to Woods Pond
I'll add to this list later when I get home.
PM me for swimming hole/waterfall directions.
Enjoy!