Catch the train from Harpers Ferry into DC. From DC you can catch a flight up to White Plains NY, or catch a bus north to New York City.
From White Plains Airport get a shuttle to the train station (Harlem Line) in North White Plains. The train station is about 10-15 miles from the airport. Ride the train north to the Wassaic station.
From New York City catch a train north (Harlem Line)to the Wassaic station about a 80 miles north of New York City.
From the Wassaic train station you can get a shuttle from Vanessa’s Hostel in Salisbury CT. Or I’m sure there are others out there that can shuttle you to the MA state line.
You are about 1 1/2 hour drive from the train station to the MA Line. Salisbury is a nice little town to spend a few hours. You can hike from Salisbury to the MA line in about 4 hours.
Of course there are many ways to get to where your going. Good Luck.
Bilko