bicycle tour of Berkshires, Mount Greylock  and southern Vermont

Bike Vermont's Green Mountains and climb Mount Greylock

near Jiminy PeakThis challenging weekend cycling tour is based at the Maple Terrace Motel in Williamstown, Massachusetts,. The rides are 35-45 miles, with somewhat challenging climbs, and with shorter and flatter loops available every day. The north Berkshires offer extraordinary rides in the valleys between the Taconic Mountain range and the Hoosic Mountains. Our routes follow the valley trails north and south, with cycling forays into the Green Mountains and a thrilling cycling ascent and descent on Mount Greylock, the highest mountain in Massachusetts.

Cycling Petersburg Pass

Petersburg Pass

Head south from Williamstown for a few miles, and then turn west on Route 2 for a four mile, 5% grade climb up to the summit of Petersburg Pass. You'll get a panoramic view of Mount Greylock to the east, and the Catskills far to the west. Reaching the hamlet of Petersburg , NY , turn south to ride for several miles in the shadows of the Taconic ridge. After reaching tiny Hancock, circle back past Jiminy Peak to Williamstown, with a stop at the Store at Five Corners. For a shorter afternoon climb, reverse at the summit of Rt. 2 and enjoy the easy 4 mile descent.

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Bennington, Vermont

Bennington MonumentWe take a very scenic ride to Bennington , Vermont , with a climb along wide-shouldered Rt. 7, and a beautiful ride on Barber Pond Rd. to Bennington (I recommend stopping here for an early lunch at All Days and Onions). We love to check out the Bennington Fish Hatchery and the old car museum . You'll ride through 3 covered bridges followed by a scenic return through pastoral Hoosic , NY and Pownal , VT to Williamstown. 45 miles, intermediate, with rolling hills and long gentle ascents.

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Riding with no handsThe Pownal Loop from Williamstown

A shortened version of the Bennington Ride from Williamstown: After the easy climb up Rt. 7, turn left on N. Pownal Rd. just after passing Barber Pond Rd. on the right, The road winds for several miles with a couple of great descents before reaching the village of North Pownal. Turn left on Rt. 67, taking it back to Rt. 7 and on to Williamstown for a very rewarding 20 mile ride.

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cycling along the Deerfield RiverThe Deerfield

From Williamstown we pass through North Adams and head up the Mohawk Trail (Rt. 2), winding through the "Hairpin Turn" until we reach a fantastic view of the valley below at Whitcomb Summit. A couple of miles later we begin a rapid descent to the Deerfield River Valley and head up through the Green Mountains of Vermont along the river rapids. Reaching rural Readsboro , Vermont , we turn south with a 10 mile gradual descent back to Massachusetts. We'll stop by amazing Natural Bridge in North Adams before taking the back road to Williamstown.

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cycling along the Deerfield RiverAround Brodie Mountain

One of our favorite afternoon rides from Williamstown is a 28 mile loop that takes us south on Green River Rd., continuing south on the bike lane on Rt. 7 until we reach the top of Brodie Mountain pass. After you pass the former ski resort, turn right on Brodie Mountain Rd., with a climb and then a great descent that takes you to Jiminy Peak ski resort. Turn right on Rt. 43, which will take you all the way back to Williamstown, with the last 10 miles being mostly downhill. You can also take this route in reverse, with a steady moderate climb past the Store at Five Corners. After passing a beaver pond on the left, turn left on Whitman Rd. and enjoy a quick climb to a field with a stone wall, where you may wish to stop and enjoy the view of Jiminy Peak. A steep descent takes you to a left turn on Brodie Mt. Rd., followed by a left on Rt. 7, and it's downhill all the way back to Williamstown.

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Ashuwillticook Rail TrailAround Mount

This ride takes back-roads through North Adams , and continue on the wonderful Ashuwillticook Rail Trail . through Adams to Cheshire . (the only flat section of ride on this tour). We cross over to Lanesborough as we circle Mount Greylock , the highest peak in Massachusetts . A moderate 3 mile climb on wide-shouldered Route 7 beside Brodie Mountain offers some of the most exquisite views in New England . You'll enjoy the continuous 10 mile descent all the way back to Williamstown, "The Village Beautiful" with a stop at the Store at Five Corner.

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Over Mount

Cycling Mount GreylockWe head south from Williamstown on wide-shouldered Rt. 7 toward Mount Greylock (elevation 3491') . This is the best ride in Massachusetts , newly repaved and should be open after being closed the past couple of years for total reconstruction. The 12 mile climb from Lanesborough to the summit averages 6% grade, with some sections considerably steeper. The 6 mile descent on the other side to North Adams is awesome if your brakes work.

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Williamstown attractions

While in Williamstown you might enjoy visiting the Clark Art Museum and the Williams College Museum of Art. Mass MOCA (Museum of Contemporary Art) has massive exhibits, and a performance on Friday evening.

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Border to Boston
AMC Worcester
Boston - Cape Cod
Boston routes
Cape Cod
Central Mass.
Charles River Wheelmen
Narragansett Bay Wheelmen
North Shore
Pioneer Valley
Rail Trails
Seven Hills Wheelmen
Massachusetts cues by town


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