i dont know what kind of accumulation they have out there or what kind of plow service, so here are some worst case scenario alternatives. where rt 7 and 112 meet in CT, the AT crosses there and there is a parking lot. if it is unusable you could go down to the friendly folks at the mountainside cafe .5 miles north on 7 and they would probably be nice to you. as would the folks at falls village. the parking lot by the great falls may be open too, since its municipal. the trail out of falls village is the road, follow the blazes over the bridge, stay right and the parking lot is like .75 miles by lovely great falls. (good swimming! go for it!) the best jump off spot in CT is the lot a mile out of salisbury, as it is a hop skip and jump away from the glorious lions head and the great taconic ridgewalk, with riga shelter (dope spot) and bear mountain, then sages ravine (would be so splendid this time of year) there are three parking lots on 41 between salisbury and sheffield MA the AT crossing, the undermountain trail, and the race brook falls trail. try all three, and barring that ask someone in moderately friendly salisbury. there is a woman who runs a hiker b&b in salisbury, her info is in wingnut.
i only ridgeran CT, so thats all i can do for you. have fun i am jealous.
milo