I was offered a teaching job at VTC this summer while visiting my mom in West Brookfield. A little too long of a commute for me from NY though.
There is a great trail really close to you guys called Cram Hill Rd. in Northfield.
You can take it from the top off of 12A, or the bottom from Brookfield Center just past the church but before the dairy farm. It's easier to find from the top it starts out as a few miles of normal dirt road that is still maintained but then you'll find the abandoned portion that connects down to the intersection of Roxbury Line Rd and Davis Acre Rd. The middle section is pretty rough and washed out that you wont be able to pass unless you have a highly modified rig. You can kill the better part of a day going at it from the top and the bottom.
:link failure: just google map "Cram Hill Road, Northfield, VT" and look at the topo of it..