This 4 day tour originates in Great Barrrington, Massachusetts, and includes rides in Massachusetts, Vermont, New Hampshire, New York State, and just a bit of Connecticut.  Each day offers a longer route of 80-90 miles with substantial climbs, and a shorter alternative route varying from 45 - 70 miles.  .

 

 

Day 1:  Great Barrington to North Adams.    The longer route leaves Great Barrington going south, passing through Sheffield, Canaan Connecticut, and the southern Berkshire hilltowns of Mill River, Monterey and Tyringham.  The shorter route leaves Great Barrington going north, connecting with the longer route in Stockbridge.  The  riders follow the same course until they reach Lanesboro.  Here you have a choice of climbing and descending 3450' Mount Greylock, or going around the mountain on the Ashuwilticook Rail Trail.  A third alternative is to follow Rt. 7 to Williamstown and then Rt. 2 to North Adams, the end of the day's ride.  The long option is 85 miles, and the shorter version is 54 miles.

 

Day 2:  North Adams, MA to Brattleboro, VT:  We leave North Adams via Route 2 (the Mohawk Trail), with a continuous ascent and a magnificent view back at the North Berkshire area.  At Whitcomb Summit, you'll take a steep descent (check your brakes) to the Deerfield River.  Here the proposed route goes east to Charlemont, and then climbs again to Jacksonville, Vermont.  A delightful alternative is to follow River Rd. west and north to Readsboro, Vermont and take Rt. 100 to Jacksonville.  (Some of this route will be used for the return on the next day, however).  From Jacksonville, you'll take Green River Rd and other rural routes to Rt. 9 just outside of Brattleboro.   Those wishing for some extra mileage may then continue on Rt. 9 into New Hampshire, and take the River Road loop that passes through the village of Westmoreland..  The basic route is 52 miles, and with the extra loop added is 80 miles.

 

Day 3:  Bratttleboro to Bennington, Vermont.  From Brattleboro, you'll take Rt. 30 north, then following Dover Rd. and other back roads to Rt. 100, taking it south to Wilmington.  Continue on Rt. 100 to Heartwellville, where you'll begin a climb on Rt. 8.  This takes you to Rt. 9 for a moderate ascent and great descent to Bennington, 64 miles.   An extra loop takes riders to North Bennington and Hoosac, New York, for a total of 92 miles.

 

Day 4:  Bennington to Great Barrington, MA:  The return to Great Barrington begins on Barber Pond Rd. to Rt. 7 in Pownal.  Do not take Rt. 7 south from Bennington.  North Pownal Rd. is a roller coaster all the way to Rt. 346.  The base route connects with Rt. 7 just outside of Williamstown, MA, while an alternative climb takes Rt. 345 to Rt. 22 in New York State, then the Petersburg Pass climb on Rt. 2, connecting with the basic route south of Williamstown.   From here you'll take Rt. 43  to Rt. 22 in New York, and Rt. 20 back to Hancock, MA.  Follow Rt. 41 to West Stockbridge, and then take Rt. 102, West Center Rd.,  West Rd. and Alford Rd. to Great Barrington.  Basic route is 71 miles, and you'll ride 79 miles if you add in the Petersburg Pass climb.