South Egremont-Sheffield easy ride
Umpachenee Falls (medium route)
Distance: 33.3 mi, Total elevation: + 1041 ft.
This classic Berkshire ride starts out with some easy cycling along the flat flood plain of the Housatonic River through Sheffield farmland 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 Umpachenee Falls (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
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.
Mount Washington – North Egremont climber
We head west to the foot of the Taconic mountains. The long version continues to the mountain village Mount Washington, then reverses course, joins the short verion on the back roads of North Egremont and Alford.
Long version: Mount Washington, North Egremont and Alford
Short version: North Egremont and Alford
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.