From NYC · Route 8 along the Farmington River

Full-day version that starts in New York City: it adds the ride there and back to Route 8 along the Farmington River. Here is what you'll find on the core stretch:

The road that links the Berkshires with northwest Connecticut: MA-8 leaves West Becket, passes Otis and Sandisfield, follows the West Branch of the Farmington River through New Boston and enters Connecticut along Colebrook River Lake to Winsted. It's 26 miles of easy curves by the river, good for a mixed pack or for closing a loop with Jacob's Ladder. There are no services between Otis and Winsted, so fuel first. Expect anglers and kayakers parked in the river bends.