There's certanly an opportunity to do what you'd like in Kent. However, to hit Kent on the way from PA to NH is terribly out of your way! If you choose to stop in Kent I recommend that you go north on NY I87, I84 East to NY Route 22 North, to NY, then CT Route 55 East, to US Route 7 North into Kent and the junction with Route 341 West. Follow Route 341 West over a bridge and take the first right onto Skiff Mountain Road. Follow Skiff Mountain Road along the Housatonic River, and when the road veers away from the river uphill, take your first (and only) Right onto a dirt road. Follow the dirt road along the river to a gate (it's a couple of miles). Park at the gate and follow the AT North for 1.3 miles to the Stewart Hollow Shelter and campsite. Alternatively, stay on Route 341 past the Skiff Mountain turnoff for about a third of a mile and look for a white oval AT trail crossing sign. Park at the turnout across from the sign and hike south, steeply uphill for .3 miles to Mount Algo shelter and campsite. Please note that no fires are permitted on the AT in Connecticut and that you need to stay at designated campsites. Our protected trail corridor is very narrow and stealth camping may put you on private property. To continue to NH from Kent, go North on Route 7 into MA and follow Route 7 into Stockbridge. In Stockbridge, Route 7 will go right at a stop sign, pass through Main Street. Just after "downtown" watch for Route 102. Go straight on Route 102 where Route 7 veers away to the left. Route 102 takes you to the Mass Pike, I90, which will get you to the highways to reach NH.
_The Walking Stomach, AMC Ridgerunner Kent,CT_