Where on the cape do you go? I vacation in Eastham. Little Overhead Surf Shop is located in Eastham and Sebastian (the owner) teaches kitesurfing at
Sunken Meadow beach in Eastham. I don't kite surf but do enjoy watching.
There is also a shop in Dennis that teaches kite surfing but I don't know the name of it.
So yes, you can kite surf the bay.
There is a New England Kite Surfing group on Yahoo groups - go there and check NEKS or something like that.
You can snow kite on any public field or frozen pond / lake that is large enough.
Hubs in New England center around those riders and customers of Powerline Sports (NH) and the Stormboarding folks (VT) - you can get to either of
their sites by googling the names.
I think there are some riders in CT who have posted on other forums but I can't remember.
Depower Quiver: 14m Gin Eskimo, 10m Gin Eskimo III, 6m Gin Yeti, 4.5m Gin Yeti (custom bridle and mixer)
Fixed Bridle Quiver: MAC Bego 400, JOJO ET Instinct 2.5 & 5.5, Lil Devil 1.5, Sting 1.2
Rides: Ground Industries