Cycling the Berkshires from Lenox MA

These routes start from the Apple Tree Inn in Lenox MA.

Hancock Shaker Village: Soon after setting out on the 26 mile round trip from Lenox, a short climb over Lenox Mountain yields a panoramic view of Stockbridge Bowl and the craggy face of Monument Mountain. Spend a couple of hours at Hancock Shaker Village, with its wonderfully preserved shops, kitchen, barns and heritage garden cue sheet map

Stockbridge, Monterey and Tyringham: We start out past "Gilded Era" mansions in Lenox and through rural farmland on our way to popular Stockbridge. The ride continues along the edge of Beartown State Forest to tiny Monterey, then drops down to the Tyringham Valley. Have lunch in Lee before returning to the Apple Tree Inn along Undermountain Road, for a total of 45 miles. Cue sheet map

Alford and Stockbridge: We check out of our rooms at the Apple Tree Inn in the morning, but leave our cars here as we head out on a 35 mile ride through Stockbridge and past the Norman Rockwell Museum. After cycling along the rapids of the Housatonic river, we pass through tiny Alford and stop for lunch in West Stockbridge. We often take a break from the 2 mile moderate climb out of West Stockbridge for a walk through the Berkshire Botanical Garden. This ride is 35 miles. cue sheet map


Lenox-Becket loop This ride heads east to Becket MA, one of the Berkshire "hilltowns" with some steady climbing and a long descent to Pittsfield before returning to Lenox . cue sheet map

Housatonic River ride Follow the course of the Housatonic River from Lee and Lenox to where it enters Connecticut, then back for a complete loop. cue sheet map

Lenox-Williamstown This long ride starts similarly to the shorter Hancock Shaker Village ride but continues past two large lakes through Pittsfield, Lanesborough and New Ashford before circling back after entering Williamstown. cue sheet map


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