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Within a single, hard day's effort out of New York City solely by pedal, the Massachusetts Berkshires are more easily accessible by train at the upper end of the Harlem Valley line of Metro North.
Users need to be aware that trains north of Southeast run every other hour.
Sheffield and Great Barrington play host to NYCC's annual Memorial Day Weekend.
The Appalachian Mountains climb higher in the Berkshires than their milder cousins in Connecticut. With deep, secluded valleys like Tyringham, and open, gentle lowlands in the Housatonic Valley, riders have a plethora of quiet, country roads to ramble on.
Cyclists are reminded to limit riding on Route 7 to short sections as it is less than bike-friendly in sections.
|Bash Bish Shorter||B||56||3 out of 5|
|Bash-Bish Classic||A, B||89||4 out of 5|
|Norman Rockwell loop from Sheffield||B, C||43||2 out of 5|
|Alford / West Stockbridge / Sheffield Loop||B, C||49||3 out of 5|
|Waterbury, CT-Sheffield, MA||A, B||55||3 out of 5|
|Sheffield to Poughkeepsie via Copake Falls & Pine Plains||A, B||64||3 out of 5|
|Wassaic to Poughkeepsie via 3 state, 5 counties & 3 mtns||A||116||5 out of 5|
|3 Mtns in CT & MA: Skiff Mtn, Sharon Mtn & Mt Everett||A||85||5 out of 5|
|Wassaic/Poughkeepsie via 2 Mtns in 3 States||A||100||5 out of 5|
|North White Plains to Sheffield||A, B||98||4 out of 5|