KenR, July 2010:

Sharon + I started in Canaan and rode the main route with variation B on a sunny weekend day, and it seemed better than ever. Saw lots more people out bicycling than previous times. Felt like mostly little car traffic.

Some notes on road conditions:

  • bridge construction starting on Lower Rd around mile 1.6 (we rode thru successfully the day before sign said it would start -- so not sure what is the alternative to deal with it).

  • mile 5.5 -- Clayton Mill River Rd under construction. The part we saw had a dirt surface, so we rode Variation B instead (which worked fine, though I'll be glad for a nice surface on that section of the main route, riding alongside the Konkapot River)

  • mile 22.1 -- bridge construction on rt 7 just south of Stockbridge. Open but with narrow traffic lane.

  • mile 44.5 -- Round Hill Rd pavement getting eroded. (while surface of alternate dirt road shortcut looked smooth and recently scraped at both ends).

Joel M, June 2008:

rode the Southern Berkshires Tour on June 19, 2008. I did the basic route. It is an excellent ride, hilly but without any truly daunting hills. I make the following observations: 1: The dirt road shortcut at mile 43.7 is officially closed. From what I see of the road you would need to be a mad mountain biker with reaklly fat tires and an attitude to even think of it. 2: The Shays rebellion monument is prominently displayed on the left side of the road just before the left turn onto Rebellion Road at mile 50.6 3: The Weatogue dirt road is in adequate condition for skinny tires, assuming dry weather mile 60.6 Thanks for the ride.

[ Ken responds: Thanks, I removed that dirt shortcut from the cue sheet ]

KenR, May 2006:

Sharon and I started in Salisbury, tried a variation to the south, a long loop down through Kent and Litchfield CT. Then rejoined main route at Mill River. Then abandoned the route when ran into heavy rain at Stockbridge, took Rt 7 south..

Some new paving (somewhat coarse-stone) on southern section of Lake Buell Rd, but southern section of Monument Valley Rd was getting more eroded. As a retreat in the rain, Rt 7 south from Stockbridge to Sheffield to Silver St worked OK. Silver St worked for us as a good way across the hill to Rt 41.

For our southern variation, we started by riding Rt 44 West from Salisbury to Lakeville, then Rt 41 South to Sharon and on to Amenia Union and into New York state, then Dutchess County Rt 3 southeast back toward Kent, which becomes Rt 341. Rt 341 east from Kent soon becomes a long climb with some sustained steeper sections, but then we liked the terrain up high, and much of the riding east and south on 45 and 341 to the junction with 202. Rt 202 East started OK (though somewhat coarse and eroded pavement) but felt like less fun as we got closer to Litchfield, with more hills and more traffic.

north of Litchfield, we got on the Norfolk Rd, which becomes East St. Rather nice at first as far as Rt 4. Still nice as we continued further, but pavement got coarser and hillier, and we joined Rt 272 into Norfolk. Rt 272 North from Norfolk into Massachusetts got hillier, and the downhills didn't seem very rewarding (just straight and steep). (Seems like going from CT into MA to Mill River further west by the main route on the cue sheet is much nicer for us.)

KenR, September 2005:

Sharon and I rode the route on a weekend day with Variations A and Z, and had a pleasant + pretty ride.

The pavement on Clayton - Mill River Rd was less rough than we remembered last time. But some very rough spots on Lake Buell Rd. There were some rough sections in the midst of the fun descent on Lenox Rd, including (I thought) one bad rough spot in the midst of that uphill curve right, just where we were trying to carry some speed up the hill. Bridge-repair construction at the bottom of the last big downhill on East Alford Rd.

November 2004, KenR:

Sharon and I started in Sheffield MA early on a weekend day and rode much of the northern half of the route -- but we omitted Stockbridge. Instead we visited Monterey, Tyringham valley, Lee, and Lenox.

We started going east from Sheffield up the long but not real steep hill of County Rd. Then joined the main route north of Mill River. Then Right on Adsit Crosby Rd, Left and north to Hartsville, and continue north on Hatchery Rd, then Right on Rt 23 East to Monterey, where we stopped for a snack at a nice bakery-coffee shop.

Turned Left onto Tyringham Rd. Not a big climb, but some steep sections. Downhill was kinda steep, would have been better with some more interesting curves. Left on Main Rd northwest -- the Tyringham valley is pretty -- some say the prettiest valley in the Berkshires -- but to us it seemed like we could remember lots of prettier nicer riding in Columbia and northern Dutchess counties.

Continued north on Tyringham Rd, then some traffic to handle with Rt 20 into Lee. Where we made another stop at a nice bakery-coffee shop on the main street.

Then north on Center, Columbia, Crystal, Housatonic to East. East was hilly without much reward for the hills. We kept going until we reached our route from the north which we had ridden over the summer, then east on New Lenox Rd.

South on Roaring Brook Rd which turned to dirt but had nice views of the water, especially in late fall season with most of the leaves gone. Then Woodland Rd back down to Mill St.

Then we decided to go to Lenox, and we tried Mill St and Walker St to East St, but this hill was steeper, so I think next time we'd take Crystal to Housatonic instead, since Housatonic worked for us a nice way to ride into Lenox -- where we found yet another nice coffee shop.

We exited Lenox on Cliffwood Rd to Under Mountain Rd, which had a horse farm and some view -- but some extra climbing -- and then rejoined the main route on Richmond Mt Rd.

The rest of the main route down to Sheffield was a lot of fun.  Although the variation was OK, and maybe better than the portion of the main route it replaced, we felt it still wasn't as good as several other sections of the main route.

Conclusion: The Southern Berkshire loop is good, and the Around Mt Greylock loop is good, but we haven't found a good loop in the Berkshires that connects in between those two.

May 2003, KenR

To help prepare for an upcoming bicycling event, I spent some time driving with my car on many roads on and nearby this route.  The big result was that I found a nice set of roads on the east side of Rt 7 between Egremont and Canaan, so at last I could see a couple of reasonable alternatives (Variations Y and Z) to those 8 miles on Rt 41 with no shoulder in Massachusetts (since Variation X was the original route when we first published this on the website). 

But the change was more radical than we expected, since the new roads east of Rt 7 are more naturally part of a loop from Canaan CT -- one which does not include Salisbury (which was the original start point of the route).  So that's why the main route now starts in Canaan, but still retains alternate start-finish variations to Salisbury.

I also found some improvements just north of Egremont, which have been incorporated into cue sheet.  One key improvement is to go around the dirt section of Seekonk Cross -- the dirt had gotten pretty rough.  The other is to take McGee and Creamery to get to Rt 23 (instead of the original route which went all the way on Seekonk Cross).

Notes on specific roads: 

  • Clayton Mill River Rd has gotten somewhat rough -- might consider the road toward Southfield if you're averse to rough pavement.  But we still think Clayton Mill River Rd is a little prettier.
  • Country Rd and Maple Ave (Variation C) between Mill River Great Barrington Rd and Sheffield was in good condition.  Could be helpful for folks looking for a much shorter route in the southern Berkshires.

August 2002, KenR

On a hot Saturday, Sharon and I rode the whole route (starting from Salisbury, with Variation Z, and finishing with part of Variation X), except for a variation which avoided a few miles of Route 41 just south of South Egremont (but nothing in Variations Y or Z).  The route felt as nice as ever, seemed like less traffic than some previous times.  The first 23 miles to Mill River seemed especially pretty and pleasant (made me think it might be worth trying a shorter loop which focused more on that area). 

Some ruts in the road surface in the first part of the descent on Lenox Rd.  And some of pavement on the northern section of Seekonk Cross is getting broken up -- still reasonable to ride, but if it gets worse it would be bothersome.  The dirt sections on Weatogue and Seekonk Cross were in reasonable condition. 

Seemed like less traffic on Route 41 South this time.  Perhaps the traffic on Route 41 south-bound is worse on Sunday afternoons.  We noticed that the lack of shoulders is worse in the Massachusetts section than in the Connecticut section of Route 41. 

We tried a variation to avoid part of Route 41 by using Sheffield Rd and Bow Wow Rd, but then discovered that part of Bow Wow is dirt -- as are lots of other roads between Route 7 and Route 41 around Sheffield MA.  But Sheffield Rd and the paved part of Bow Wow were nice, and we like the idea of an alternative to some of Route 41 in Massachusetts -- but we haven't found it yet. 

July 2002, Greg

These are Ken's notes from a phone conversation: 

Rode only a section of the route -- the first part from Salisbury CT thru Mill River to Stockbridge MA.  Fun experience, would do it again.  Less hilly than had been afraid of.

Called in on cell phone from while stopped in between two corn fields.  Liked seeing the quarries and the Twin Lakes.  In Stockbridge, bought a rather helpful Massachusetts bicycle route map. 

Only one problem with the cue sheet directions for this part:  at one point it seemed like Clayton Mill River Rd went Straight (while some other road goes Left) -- and going straight did lead to Umpachene Falls which the cue sheet said came next. 

[ the cue sheet directions have since been modified

Story of this route

Ken's story:  Years ago we started exploring the Berkshires of southeastern Massachusetts as part of giant one-day routes with Columbia county, NY.  One time doing a big ride with Tony, we saw a Berkshires bicycling guidebook at the food stop in South Egremont and bought it and carried it home.  That gave us some other ideas for roads in northeastern Connecticut, and also a big 100-mile route that included Richmond Mt Rd going by the Kripalu Center and Stockbridge Bowl.  

We soon found that the region had lots of fun bicycling on its own, with no need to share a long route with New York roads.  After several more exploratory rides, we settled into doing the loop starting from Salisbury using what are now Variations A and X, but continued working on improvements and variations. 

Then in May 2003, I found a nice set of roads on the east side of Rt 7 between Egremont and Canaan, so at last I could see a couple of reasonable alternatives (Variations Y and Z) to those 8 miles on Rt 41 with no shoulder in Massachusetts (since Variation X was the original route when we first published this on the website). 

But the change was more radical than we expected, since the new roads east of Rt 7 are more naturally part of a loop from Canaan CT -- one which does not include Salisbury (which was the original start point of the route).  So that's how the main route came to start in Canaan, but with alternate start-finish variations to Salisbury.

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