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 climbs, designed for upper intermediate to advanced cyclists. We recommend dinner at the Old Mill Restaurant in nearby South Egremont. While in the area, see what’s happening at the Mahaiwe Theater Performing Arts Center in downtown Great Barrington.

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A choice of routes are provided below:

Friday afternoon

A choice of an easier ride to Sheffield or a couple of steeper ride options to North Egremont and Alford

Easy ride: South Egremont-Sheffield

Distance: 18.1 mi. Elevation: + 594 ft with a short section of unpaved road)

View/print South Egremont-Sheffield PDF cue sheet

Route at RideWithGPS
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27 mile North Egremont and Alford ride

Distance: 26.6 mi. Elevation: 1686 ft

View/print 27 mile PDF cue sheet

Route at RideWithGPS
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Print PDF cue sheet (requires RWGPS login)

17 mile North Egremont and Alford ride

Distance: 17 mi. Elevation: + 1014 ft. (eliminates Mount Washington climb)

This ride begins at the Windflower Inn. We head west to the foot of the Taconic mountains and then take back roads to North Egremont. From there, Rt. 71 to the New York state line is a straight and scenic a roadway with views of the mountains the entire way. We circle north through Alford before looping back through Alford to the inn.

View/Print 17 mile PDF map and cue sheet

Route at RideWithGPS
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Saturday

Mill River (medium route)

Distance: 34 mi, Total elevation: + 1240 ft.

This classic Berkshire ride starts out with some easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland to Mill River, with an optional gravel side route to Umpachenee Falls. The return includes an exhilarating downhill ride back to the Housatonic River before returning to Sheffield, where you may want to stop by the oldest covered bridge in Massachusetts.

MILL RIVER PDF CUE SHEET

Route at RideWithGPS
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Twin Lakes and Mill River (long route)

Distance: 57.1 mi Elevation: 2380 ft

TWIN LAKES MILL RIVER PDF CUE SHEET

Route at RideWithGPS
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Sunday

Alford, West Stockbridge and Stockbridge

Distance: 37 mi. Elevation: + 2100 ft (medium route)

Ride north along the edge of the Taconic Mountains and through tiny Alford to West Stockbridge, where you can visit Baldwin’s General Store and Hoffman Pottery. The ride continues on to Stockbridge, MA, home of Norman Rockwell Museum. and Chester wood, the studio of Lincoln Monument sculptor Daniel Chester French. The return is along the rapids of the Housatonic River to Great Barrington and back to the inn.

ALFORD-W. STOCKBRIDGE-STOCKBRIDGE PDF CUE SHEET

Route at RideWithGPS
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Alford, West Stockbridge, Richmond and Stockbridge (long version)

Distance: 47.4 mi. Elevation: + 2661 ft

ALFORD-RICHMOND-STOCKBRIDGE PDF CUE SHEET

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Other rides

Monterey and Tyringham

Distance: 39.8 mi. Elevation: + 2040 ft

This scenic 40 mile ride goes through downtown Great Barrington Massachusetts and heads out of town up “Three Mile Hill. We circle around Lake Buel, then top to check out the Berkshire Fish Hatchery in Hartsville. Continue on to Monterey, MA, and stop for refreshments at the Monterey General Store. The ride continues past Lake Garfield with a sweeping descent into the Tyringham Valley. Make sure to stop to view the Gingerbread House in Tyringham just before taking a left to South Lee.
After turning left on Rt. 102, you’ll see an impressive dam and spillway on the left, part of a still-operating paper mill. Continue on to popular Stockbridge, whose attractions include the Red Lion Inn, Berkshire Botanical Garden, the Norman Rockwell Museum, and Chesterwood, home of Lincoln Monument sculptor Daniel Chester French. The return from Stockbridge follows the flowing rapids of the Housatonic River back to Great Barrington.

Tyringham Ride PDF cue sheet

Route at RideWithGPS
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Mount Washington, Bash Bish Falls, Copake NY

Distance: 40 mi, Max Grade: 10.0 %, Elevation: 3400 ft

This is one of the most challenging rides in the Berkshires, with an ascent of several miles from South Egremont, riding past Mount Everett, the second highest mountain in the state to the end of the road in tiny hamlet of Mount Washington. Here we take an amazing descent down the winding paved road past Bash Bish Falls to the community of Copake Falls, NY. Ride on the paved Harlem Valley Rail Trail before cycling for several miles through New York State farm country. The ride crosses a pass in the Taconic Mountains for the return to South Egremont.This ride is approximately 40 miles. View at RideWithGPS