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The Berkshires
The Berkshires
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.
| Name | Level(s) | Distance | Difficulty Rating |
|---|---|---|---|
| Wassaic to Poughkeepsie via 3 state, 5 counties & 3 mtns | A | 116 | 5 out of 5 |
| [Berkshire Weekend] Lakeville All Class C Route | C | 41 | 2 out of 5 |
| [Berkshire Weekend] Norman Rockwell loop from Sheffield | B, C | 43 | 2 out of 5 |
| [Berkshire Weekend] Lakeville Picnic Gravel | A | 49 | 4 out of 5 |
| [Berkshire Weekend] Bash Bish Shorter | B | 56 | 3 out of 5 |
| [Berkshire Weekend] Umpachene Falls Loop | B, C | 20 | 1 out of 5 |
| [Berkshire Weekend] Hancock Shaker Village | B, C | 51 | 3 out of 5 |
| [Berkshire Weekend] Stockbridge Bowl Loop | B, C | 32 | 2 out of 5 |
| [Berkshires Weekend] Great Barrington to Wassaic | B, C | 34 | 1 out of 5 |
| [Berkshire Weekend] Mt Greylock from Great Barrington | A, B | 39 | 3 out of 5 |
