From NYC · Route 41 & Bash Bish Falls

Full-day version that starts in New York City: it adds the ride there and back to Route 41 & Bash Bish Falls. Here is what you'll find on the core stretch:

The corner where Connecticut, Massachusetts and New York meet: you leave Salisbury on Undermountain Road (CT-41 / MA-41) under the Taconic ridge, continue to South Egremont, cross to Hillsdale on Route 23, drop down NY-22 to Copake Falls and climb NY-344 to Bash Bish Falls. It's 25 easy valley miles that suit any pack. The route ends at the falls with no return leg, and the parking lot is small and fills up on weekends. It doesn't go through Mt Washington, whose roads are dirt.