Southern Berkshires Tour

  • where:  northwestern Litchfield County in  Connecticut and southwestern Berkshire County in Massachusetts.  Canaan CT (or Salisbury CT) to Stockbridge MA and Tanglewood (near Lenox MA).  

  • 68 miles, moderate hilliness (4000 vertical feet, hill index 3.4) 

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28 mile loop to Mill River and Sheffield -- Variation C : hilliness at the low end of "moderate" (1500 vertical feet, hill index 3.0) -- one long non-steep climb.

Main route [bhvo1] : on Bikely | KML | GPX

GPX file has separate tracks for a) east side Canaan to Tanglewood, b) west side Tanglewood to Canaan.
+ separate tracks these variations: vB) alternate to avoid construction 2010; vC) shortcut to make 28-mile loop; 
vA) Salisbury start, vZ) Salisbury finish, vZ) Silver St shortcut to Salisbury finish.

Short loop 28 miles [bhvo1c] : on Bikely | KML | GPX

  • Salisbury start-finish:  Actually we've often started in Salisbury, Connecticut rather than Canaan: 

- - 85 miles with Variations A + Z (4900 vert ft, hill index 3.5)
- - 83 miles with Variations A + Y + Z 
- - 76 miles with Variations A + X (4800 vert ft, hill index 3.7) 

(more discussion of these three alternative further below)

  • highlights:  Variety of scenery in the southern Berkshires, farm fields and animals, lots of pleasant riding on quiet roads, several fun downhills. Story of this route
  • characteristics:  Lots of hills both small and moderate, but no single hill is really big and steep.  There's also some gentle rolling sections.  

About 1 mile on dirt.

Hill climbs:  The main route has a 175 ft climb from Tanglewood up Richmond Hill Rd at 6% average grade, and a shorter steeper section of 90 feet at 7% grade climbing north up from Stockbridge. 

Variation C has one long non-steep climb of about 300 vertical feet at around 3% grade.

Variation A has a bit over 100 ft at around 8% grade on Cooper Hill Rd east-bound. 

Variation Z has a steeper section of 150 ft at over 9% grade on Cooper Hill Rd west-bound starting from Weatogue and Rannapo Rd.  (Variation Y avoids this steep section, by joining Cooper Hill Rd the top of this climb)

Traffic:  Overall similar to many other routes on this Bike Hudson Valley website.

on Variation X:  Rt 41 south from South Egremont has 8 miles with no shoulders in Massachusetts.  This section of Rt 41 can get significant car traffic on busy weekends -- perhaps the traffic on Route 41 south-bound is worse on Sunday afternoons.

on Variation Z:  Cooper Hill Rd has two tight curves with low visibility to overtaking vehicles.  For ourselves, we don't feel special concern taking these curves in the East-bound direction in Variation A, because we're going fast down the hill.  But taking them in the West-bound in Variation Z, we're going much slower climbing up the hill and spending more time on those curves.

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more . . . 

  • Directions to Start: 

by carFrom the Taconic State Parkway or the Mid-Hudson Bridge, take Route 44 East to Amenia NY, then Route 22 North to Millerton NY, then Route 44 East into Connecticut, through Lakeville to Salisbury CT and then to Canaan CT. 

From the Kingston-Rhinecliff Bridge, take Route 199 East, to Route 22 North to Millerton NY, then Route 44 East into Connecticut, through Lakeville to Salisbury CT and then to Canaan CT. 

From Connecticut, take Route 7 to Canaan CT.   Or to start in Salisbury, take Route 44 West from Canaan. 

by train:  From the Wassaic station on the Metro North Harlem Valley line from New York City, it is around 20 miles to the start of this route in Salisbury CT.  Several possible routes -- see Harlem Valley Rail to Millerton to Connecticut for some ideas. 

Other start points:  Salisbury CT, Stockbridge MA (near Mass Pike), South Egremont MA (on Rt 23).  

  • maps:  You should have detailed road maps of Litchfield County, CT and Berkshire County, MA to do this route (see Road Maps).  There are several roads whose names are not well indicated on the road signs, especially in Massachusetts. See also digital mapping + GPS above.
  • comparing the Salisbury finish variations:  Variation X is the shortest, gentlest, simplest -- but also with the most sustained traffic interaction with high-speed vehicles and no shoulders on Route 41 in MA, and not the most interesting scenery.  Variation Y has high-speed traffic interaction on Rt 7, but we find the lane width and shoulder mostly reasonable, though not real wide.  Variation Z has the steepest hill-climb and the traffic concern of two low-visibility curves -- but also the most interesting scenery.

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and more . . . 

  • lots of road bicycling in the Berkshires . . . 

- - Western Massachusetts bicycling map, by Rubel BikeMaps

Very helpful resource -- we bought our copy on the Web.  In addition to recommended bicycling roads, it also identifies which roads are unpaved, which ones have steep hills -- and where to stop for ice cream. 

- - The Bicyclist's Guide to the Southern Berkshires, by Steve Lyons

25 road routes described with abundant local color.  (Freewheel Publications, Lenox MA, 1993)

- - Berkshire and Connecticut Valley Bicycle Route Survey 

- - Berkshire Cycling Association 

- - Berkshire Visitors Bureau 

  • Connections to other routes: 

The Harlem Valley Rail to Millerton to Connecticut and Harlem Valley Rail to Trail to Falls routes go within about 5.4 miles of Salisbury.  But the shoulders on high-speed Route 44 between Millerton and Salisbury are narrow or non-existent at some points, though often reasonable.  There are at least two other connecting routes, between Sharon and Salisbury, with less motor vehicle traffic. 

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