Tag: Lenox

CycleAbility Challenge, June 2-3, 2018

The CycleAbility Challenge provides options of 30, 60 and 100 miles.  The event has raised over $5.8 million for Special Olymics New York since its inception in 1990. The tax-deductible pledges support Special Olympics New York-Hudson Valley Region.

Cycling the Berkshires from Lenox, MA

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Alford Town Hall

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 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

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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.

Tyringham bicycle loop

This scenic ride with 35-50 mile options starts from downtown Great Barrington Massachusetts and heads out of town up “Three Mile Hill. We circle around Lake Buel, then top to check out the Berkshire Fish Hatchery in Hartsville. Continue on to Monterey, MA, and stop for refreshments at the Monterey General Store. The full continues past Lake Garfield with a sweeping descent into the Tyringham Valley. Make sure to stop to view the Gingerbread House in Tyringham just before taking a left to South Lee.

After turning left on Rt. 102, you’ll see an impressive dam and spillway on the left, part of a still-operating paper mill. Continue on to popular Stockbridge, whose attractions include the Red Lion Inn, Berkshire Botanical Garden, the Norman Rockwell Museum, and Chesterwood, home of Lincoln Monument sculptor Daniel Chester French. The return from Stockbridge follows the flowing rapids of the Housatonic River back to Great Barrington.

For a longer ride, continue from Tyringham to Lee and Lenoxdale to Lenox, where Undermountain Road is a scenic alternative route to the Tanglewood grounds. From there, take Hawthorne Road and Prospect St. past Stockbridge Bowl, with a nice descent past incredible Stockbridge mansions to rejoin the shorter route.


Route at RideWithGPS
View and print cue sheet
View and print map
GPX file

TCX Course