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 this corner of the Massachusetts. Here we turn toward New York State, taking an amazing descent down the winding paved road past Bash Bish Falls to the community of Copake Falls. Ride for a few miles 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
Start: Windflower Inn, Rt. 23 E., Great Barrington, MA 01230 , near South Egremont
Distance: 40 mi Max Grade: 10.0 % Elevation: Gain and descent, 3400 ft
Mount Everett ride at RideWithGPS
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TCX Course
Cue Sheet from RideWithGPS
| Turn right on Rt. 23 from Windflower Inn and enter South Egremont, MA | |
| Take the 1st left onto MA-41 S/N Undermountain Rd | 0.9 mi |
| Slight right at Mt Washington Rd | 1.0 mi |
| Slight left at East St | 5.4 mi |
| Turn left to stay on East St | 6.2 mi |
| Sharp right at West St | 9.8 mi |
| Turn left at Falls Rd | 11.9 mi |
| Sharp left at Valley View Rd | 15.0 mi |
| Take the 1st right to stay on Valley View Rd | 15.1 mi |
| Turn right | 19.1 mi |
| Turn right at NY-22 N | 19.2 mi |
| Take the 2nd left onto Trout Brook Rd | 20.1 mi |
| Turn right at Empire Rd | 21.0 mi |
| Slight left at Co Rd 7a/Main St | 22.4 mi |
| Turn left at Farm Rd | 22.8 mi |
| Turn left at Overlook Rd | 25.1 mi |
| Take the 1st right onto Black Grocery Rd | 26.0 mi |
| Take the 1st left onto Underhill Rd | 26.9 mi |
| Sharp right at NY-22 S | 28.3 mi |
| Turn left at N Mountain Rd | 29.8 mi |
| Take the 1st right to stay on N Mountain Rd | 30.0 mi |
| Turn left at Breezy Hill Rd | 30.6 mi |
| Turn left at NY-23 W | 33.5 mi |
| Take the 1st right onto Oxbow Rd | 33.9 mi |
| Turn right to stay on Oxbow Rd | 34.7 mi |
| Turn left at Prospect Lake Rd | 35.7 mi |
| Turn right at MA-71 E/Egremont Plain Rd | 37.2 mi |
| Slight right at Creamery Rd | 38.4 mi |
| Take the 1st left toward MA-23 E/MA-41 N | 40.0 mi |
| Turn left at MA-23 E/MA-41 N to return to Windflower Inn | 40.0 mi |
This ride from Great Barrington, MA climbs for several miles along the side of Mount Everett, the second highest mountain in Massachusetts, before steeply descending to Copake Falls NY, near Bash Bish Falls. From here take the Harlem Valley Rail Trail parallel to Valley Road, then local roads south to Millerton NY. the ride swings east to Falls Village CT, then back through Canann CT and Sheffield MA to the start location. Steep climbs and descents at the beginning, followed by flatter terrain
in New York and Connecticut farm country.
View at RideWithGPS
Start: Windflower Inn, Rt. 23 E., Great Barrington, MA 01230 , near South Egremont
Distance: 57 mi
Max Grade: 10.0 %
Elevation: Gain and descent, 3410 ft
View a 54 mile version of this ride that goes around Mount Everett, elevation (gain and descent) 2924 ft.
Cue Sheet from RideWithGPS
| Head west on MA-23 W/MA-41 S from the Windflower Inn in Great Barrington MA |
0.0 mi |
| Turn left at MA-41 S/N Undermountain Rd | 0.9 mi |
| Slight right at Mt Washington Rd | 1.0 mi |
| Slight left at East St | 5.4 mi |
| Turn left to stay on East St | 6.2 mi |
| Sharp right at West St | 9.8 mi |
| Turn left at Falls Rd | 11.9 mi |
| Turn right to stay on Valley View Rd | 15.3 mi |
| Turn right | 19.2 mi |
| Turn left at NY-22 S | 19.3 mi |
| Take the 1st left onto Under Mountain Rd | 19.7 mi |
| Turn left at Boston Corners Rd | 21.7 mi |
| Turn left at Main St | 28.8 mi |
| Turn left at Dugway Rd | 36.5 mi |
| Slight left | 37.3 mi |
| Sharp left at Dugway Rd | 37.4 mi |
| Turn right at Falls Mountain Rd | 38.8 mi |
| Turn right at Water St | 38.9 mi |
| Turn left at Railroad St | 39.3 mi |
| Turn right at Sand Rd | 40.8 mi |
| Turn right to stay on Sand Rd | 44.1 mi |
| Take the 1st left onto E Main St | 44.8 mi |
| Turn right at W Main St | 45.4 mi |
| Turn right to stay on W Main St | 45.5 mi |
| Take the 1st left to stay on W Main St | 45.6 mi |
| Turn left at Ashley Falls Rd/Massachusetts 7A | 47.3 mi |
| Turn left at Egremont Rd | 53.0 mi |
| Turn right to stay on Egremont Rd | 53.0 mi |
| Take the 1st right onto Buttonball Ln | 56.6 mi |
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