We rode the Trans-Massachusetts-Trail yesterday. A series of dirt roads starting at the border of Connecticut and Massachusetts and working its way north to route 2 where it meets up with the start of the Puppy Dog Trail, which winds its way north all the way to the Canadian border (we'll be doing that one shortly). Near the end of the trip we stopped for a break in the woods to address the "call of nature" and grab a snack.

Living in Boston there’s not a lot a lot of places to practice riding on dirt, but there is the Trans-Massachusetts Trail, which hooks up with the Puppy Dog Route (maps here) at its north end and continues north to the Canadian border. We’ll be doing the Puppy Dog soon, but in the meantime the TMT makes for a good day trip, and  being a collection of roads specifically chosen for people unfamiliar with dirt riding it was a great choice for introducing Dachary to dirt.