Tour de Greylock, Sept. 15, 2022

Tour de Greylock

This is a scenic 41-mile ride, starting and ending in Lanesborough, which will take participants through the towns that surround Mount Greylock, Massachusetts’ highest peak. Organized by the Lanesborough Economic Development Committee

Pain in the Mass, Amherst MA

Pain in the Mass bicycle ride

THE PAIN in the MASS TOUR  was designed to help support The Tyler Foundation and the families affected by epilepsy.

Berkshires to Boston

Berkshires to Boston bicycle tour

South Berkshire tour from Great Barrington, MA

This weekend tour of the popular Berkshires in western Massachusetts takes you into neighboring Connecticut and New York State. All routes begin from the Windflower Inn near the Great Barrington / South Egremont town line.  Daily Ride options are 30-45 miles, with a nice mixture of a few flat roads, rolling hills and some long steady… Continue reading South Berkshire tour from Great Barrington, MA

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 and print map GPX file TCX Course

Great Barrington to Umpachenee Falls

Umpachenee Falls

Hidden away near tiny Mill River, Massachusetts is a local gem, a rolling waterfall that starts as rapids about a half mile uphill and opens up to a scenic array of water plunging over rock ledges. This small town park makes a great half day cycling destination from Great Barrington, the largest community in the… Continue reading Great Barrington to Umpachenee Falls

Great Barrington MA -Philmont NY: Tour of Massachusetts

Great Barrington - Philmont ride

Great Barrington  MA to Philmont, NY loops are provided by the Massachusetts State Bike Tour 2016. View the 76 mile ride. 60 mile ride Route at RideWithGPS View and print cue sheet View and print map GPX file TCX Course

Cycling the Berkshires from Lenox, MA

North Shore Cyclists Berkshire ride

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… Continue reading Cycling the Berkshires from Lenox, MA

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 the beautiful Ashuwilticook Rail Trail for a… Continue reading Cycling around Mt. Greylock

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 hill town, to Umpachenee Falls. On our… Continue reading Umpachenee Falls