Category: Berkshires

Hazon ride, Falls Village, CT

The Hazon Ride & Retreat is a fully-supported ride, fundraiser, and community experience for people of all cycling levels and ages. Spanning Labor Day Weekend and based at the Isabella Freedman Jewish Retreat Center. HAZON RIDE – DAY 1 2014 Route at RideWithGPS View and print cue sheet View […]

Cycling around Mt. Greylock

Mount Greylock is the highest mountain in Massachusetts. In addition to the incredible ride over the mountain there is an easier counterclockwise loop around the mountain beginning from the same location at the Williamstown Public Library. Taking back roads through North Adams to Adams, where you’ll be on […]

Umpachenee Falls

A classic Berkshire ride, starting from the Windflower Inn in Great Barrington, MA but very near the hamlet of South Egremont. It starts out with easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland, then some gentle climbing toward Mill River, a Berkshire […]

Mount Everett- Bash Bish Falls ride

Mount Everett Climb

This is one of the most challenging rides in the Berkshires, with a an ascent of several miles from South Egremont Massachusetts, riding past Mount Everett, the second highest mountain in the state to the tiny hamlet of Mount Washington, riding exactly to the end of paved roads in […]

The New England National Scenic Trail

The 220 mile New England National Scenic Trail in southern New England consists of the Metacomet-Monadnock Trail, Mattabesett Trail and the Metacomet Trail and is better known as the Triple-M Trail. The network starts at Guilford, Connecticut and goes north along the Metacomet Ridge and continues through the […]

Berkshire Cycle Touring

This scenic self-guided week-long tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut, Vermont and New York State. These routes begin from the Windflower Inn in Great Barrington, MA and two nights at the Maple Terrace Motel in Williamstown, MA. Daily Ride options are […]

Mount Greylock climb

Mount Greylock  at 3491 ft. is the tallest mountain in Massachusetts.. Notch Road from North Adams is the steeper of the two paved roads to the summit, with hairpin turns and some very steep sections in the first half of the climb. I prefer cycling from Williamstown to Lanesborough, […]

North Berkshire cycling tour

Based at the Maple Terrace Motel in Williamstown, Massachusetts.Rides are 35-50 miles with terrain varying from the flat Ashuwillticook Rail Trail to the challenging climb over Mount Greylock. Google Map for Maple Terrace Motel. Brodie Mountain / Jiminy Peak Loop with Petersburg Pass extra 7.5 mile option. This […]

Becket MA to Lenox bicycle ride

Becket hill climb

A climbing ride in the Berkshires. From Lenox, Massachusetts head east for a few miles on the nice shoulder of Rt. 20, then take local roads to tiny Becket Massachusetts. The route back through New Lenox passes several of the mansions built in the Lenox area during the “gilded […]