This three-day tour is for members of North Shore Cyclists and take us to the Berkshires' most popular attractions, with 2 nights, 3 days based at the Windflower Inn in Great Barrington, Massachusetts. Daily Ride options are 35-50 miles, with a nice mixture of a few flat roads, rolling hills and long steady climbs, designed for upper intermediate to advanced cyclists. The rides are on safe quiet country roads with very little traffic and a mix of beautiful valleys, mountains and farmlands making it one of the most popular cycling destinations in the American Northeast. This tour is usually run in the fall by NSC coordinator Gordon Harris.
Note: These routes are not arrowed. Each ride below includes a cue sheet and map for download and a link to the ride on the site RideWithGPS. For information about how to download GPS files for your Garmin Edge, go to http://www.bikenewengland.com/gps.html
Suggested Routes:
Alford-North Egremont Ride: Head out through North Egremont along the edge of the Taconic Mountains and through tiny Alford
32 miles with 2080 ft. of climb; 16 and 22 mile options.
View at RideWithGPS.
Download Cue Sheet and map
Egremont-Stockbridge-Lenox Ride This 44 mile ride takes us through three of the Berkshire's most popular towns, Great Barrington, Stockbridge and Lenox. We start through Great Barrington and begin a gentle climb up "Three Mile Hill", followed by gorgeous views in Monument Valley before arriving in Stockbridge. After a break we continue past dairy country on Lee's backroads and past huge mansions from the Guilded Age to Lenox, home of the Tanglewood Music Festival. After a break for lunch, we take beautiful Undermountain Road , then ride past Stockbridge Bowl to Stockbridge. Our return is along the Housatonic River and backroads to the Windflower Inn. 44 miles with 2400 ft. of climb.
View at Ride With GPS
Download cue sheet and map
Twin Lakes-Umpachenee Falls Ride: This 41 mile ride take us to Twin Lakes in Connecticut the returning at mile 17 through Canaan CT for a break. We head back north with an easy ride to Umpachenee Falls and a break at the general store in Mill River at mile 27, where we can stop for sandwiches. The ride is on quiet back roads and is relatively gentle, with a few modest climbs and a long exhilerating descent back to Sheffield. Total elevation for this ride is approximately 1800 ft.
View at RideWithGPS
Download Cue Sheet and Map.
Longer ride: 56 mile version that includes Falls Village Connecticut and the Toymaker's Cafe, as well as Umpachenee Falls. 56 miles with 2500 ft. of climb. View at RideWithGPS
Shorter ride: Twin Lakes only. 32 miles with 1200 ft. of climb. View at RideWithGPS
Twin Lakes- Falls Village CT Ride: This ride takes us to Twin Lakes in Connecticut, continuing to Falls Village before beginning our return through Canaan CT and Sheffield Mass. The entire ride is on quiet back roads and is relatively gentle, with just a couple of short but steep climbs. 45 miles with 1800 ft. of climb ride description page .
View at RideWithGPS
Download Cue Sheet and Map.
Umpachenee Falls. Start 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. Approximately 33 miles with 1260 ft. of climb. .
View full ride description page
Map and Cue Sheet.
View at Ride With GPS
Alford-West Stockbridge Ride Ride West Stockbridge continuing on to Stockbridge, MA home of Norman Rockwell Museum. 42 miles ride with 2600 ft. of climb View description page for this ride.
Cue Sheet and map.
View at Ride With GPS
Mount Everett , New York State Climbers may wish to try the 5 mile ascent toward the second highest mountain in Massachusetts, Mount Everett. After reaching rural Mount Washington, you may ride back down the same way, or take the steep descent to Copake in New York State, riding near Bash Bish Falls. After reaching Copake Falls, ride a few miles on the Harlem Valley Rail Trail and then continue through upstate New York fam land before returning to the inn. (Left: a view of Mount Everett from below as we begin our climb to the community of Mount Washington.) 40 miles with 3400 ' of climb. View description page
Cue Sheet and Map
Monterey-Tyringham-Stockbridge This 40 mile loop takes us through Great Barrington just like the Lenox Ride but continues on to rural Monterey, where you'll want to stop at the Monterey General Store for a break. Continue with a quick descent to pastoral Tyringham, then on through South Lee to Stockbridge where you can stop for lunch. The return is along the rapids of the Housatonic River to Great Barrington and back to the inn for 40 miles. View at Ride With GPS Cue sheet and map
Lodging: This tour is based at the Windflower Inn in Great Barrington, Massachusetts, 2 nights occupancy September 9 and 10, checking out September 11. This tour is completely booked. Contact tour organizer Gordon Harris about availability at other inns.
Meals: Full breakfasts at the inn. A group dinner on Saturday night is included with the tour price.
Other activities: For a superb first evening dining experience, try the Old Mill Restaurant in South Egremont. Check out the Mahaiwe Theater Performing Arts Center in downtown Great Barrington.
Price: Generally $250 per person including guided tour, two nights double occupancy with breakfasts and one group dinner. $340 for single occupancy . Price varies according to date and inn availability