A choice of an easier ride to Sheffield or a couple of steeper ride options to North Egremont and Alford
Distance: 26.6 mi. Elevation: 1686 ft
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.
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.
Twin Lakes and Mill River (long route)
Distance: 57.1 mi Elevation: 2380 ft
Alford, West Stockbridge and Stockbridge
Alford, West Stockbridge, Richmond and Stockbridge (long version)
Distance: 47.4 mi. Elevation: + 2661 ft
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.
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
Distance: 41.1 mi Elevation: + 3174 ft
We head west to the foot of the Taconic mountains, then reverse course, with two distance options in North Egremont and Alford.