The Berkshire Mountains Tour
The plan was for five days of riding through the Berkshire mountains in western
Massachusetts, eastern New York, and southern Vermont. I had never been there so
this was totally new territory for me. The only tricky part was partially disassembling
my bicycle and carefully packing it in a specially designed travel case so it could
be flown up there with me. Tip: Southwest Airlines lets bikes fly for $50.00 each
way. Most of the other airlines charge $100.00 to $150.00 each way.
I flew from Orlando to Albany, New York on Day One, a Friday. Both bags arrived with
no problem. The Enterprise Rent a Car facility at the airport had too many SUVs
in their inventory so they gave me a Jeep Patriot for $11.00 per day. That was cheaper
than a compact car rate!
The base of operations for the first few days of the trip would be the Days Inn
in Great Barrington, MA. From there, I would make a couple of day trips up into
the mountains to explore.
The first order of business, after checking into the hotel and unpacking, was to
swing by the local bike shop. In Great Barrington, you want to touch bases with
the terrific guys at Barrington Bike and Board. Craig is the manager. The nut for
the seat post clamp for my bike was somehow lost in transit. They didn't have a
barrel nut to fit it but they gave me another seat post clamp, no charge. I came
prepared with a selection of possible routes, which became important. Craig also
was valuable in recommending which of the routes would be best and prettiest and
which direction to do them in. He also recommended the Japanese hibachi restaurant
Shiro, which was so good I ate there three times.
The first riding day was Saturday and I headed to Bash Bish Falls up on Mount Washington.
If you do this route, and I highly recommend it because Bash Bish Falls is worth
the trek, be prepared. There is 2751 feet of climbing, which is not bad, but some
of it is very steep and will kick your butt. Seriously... very steep!
Here's the route for Bash Bish Falls: http://ridewithgps.com/routes/224613. What
the map doesn't show is that West Street is unpaved. New England dirt roads are
generally compacted well enough that they can be carefully navigated with a road
bike. Just maintain constant focus for a couple of miles and then you're back on
pavement. At 40 miles, this is one of the shortest routes of the tour but the most
There is a short hike involved getting down to the viewing area of Bash Bish Falls.
Short... but very steep. The trail is marked with arrows on trees but there are
no steps or railings. This is not a hike to attempt while wearing road shoes so
be prepared by bringing along a pair of hiking shoes or tennis shoes or sturdy Keen
sandals. Even with those, I still slipped and fell. If you're not in semi-decent
shape, I wouldn't recommend this hike. Getting back up could be difficult.
Hurricane Irene decided to pass through New England and, in fact, passed right over
the top of Great Barrington on Sunday after being downgraded to a tropical storm.
I holed up in my hotel room and watched TV all day. It really wasn't bad. I rained
steadily for 24 hours but there was pretty much no wind. The rest of New England
didn't fare so well. More on that later.
Monday morning was a new day. It was bright and sunny and I was headed out on the
Stockbridge Loop. This route took me from Great Barrington to Monterrey to Tyringham
to Lenox to Stockbridge and back to Great Barrington. Every little town along the
way was pretty and charming. Monterrey was so cute that I gawked a lot and forgot
to watch the map, straying about 1/2 mile off course. :-)
The hardest part of this route is between Monterrey and Tyringham. The locals call
it the Wall of Pain. By the time you get to Tyringham, it gets much easier. If you
go the direction I did, you go up the backside of it and it's still respectable.
If you go clockwise, you're suicidal. Here's the route: http://ridewithgps.com/routes/657437.
Be prepared for 3174 feet of climbing and some spectacular scenery over the 48.6
One day after a tropical storm passed through and it was a little breezy, 10-12
mph, but there was very little in the way of flooding or trees down in this area.
Other areas were much worse. More on that later.
People are very friendly, waving and saying hi. One lady in a car at an intersection
where I was waiting on the traffic light to change pulled up next to me and took
the time to ask if I was going straight or turning. I noticed her right turn signal
was on so I told her I was going straight but would wait to do so until after she
turned. Very nice. It made up for the one oncoming nincompoop driver who passed
another car on a two lane road by coming over into my lane, straight at me, in a
no-passing zone. Otherwise, drivers are very tolerant of cyclists in this part of
I would rate the Stockbridge Loop as a "must do".
Tuesday morning was quite foggy and, as a result, felt colder than the same temp
yesterday. I delayed an extra hour before leaving. Technically, I checked out of
the hotel but left the suitcases in the rental car and the hotel was kind enough
to let me leave it parked there until returning in two days.
Today I was headed from Great Barrington in the southwest corner of the state up
to Williamstown in the northwest corner. Here's the route: http://ridewithgps.com/routes/228803.
It's 51 miles with 2932 feet of climbing.
The first order of business was a long climb out of Great Barrington. I made my
way up to Stockbridge and then Pittsfield before turning west and heading into New
York. I stopped to take a break at an intersection and a fellow roadie stopped by
to chat. He pointed me to some places to get lunch over in New York. The town of
New Lebanon, NY was only 4.5 miles away. A mile and a half climb up the mountain
followed by a three mile ride back down. Yeehaw!!!!!
Made it to Williamstown, in the upper left corner of the state. Stopped by the local
bike shop, The Spoke, and discussed the route for tomorrow up into Vermont to look
at some covered bridges. There are reports of some road washouts caused by Irene-swollen
rivers but they may be passable by bike. As far as anyone knew, the covered bridges
around Bennington may be okay. Some of those further up into the state were washed
away or heavily damaged. Good folks at The Spoke. Stop in and see them when you're
in the area.
The travel week was also the week that the students return to Williams College in
Williamstown. All of the hotels were completely booked, even months in advance,
except the Willows Motel. I was able to get a room there for two nights. It was
nice enough and clean but I wouldn't recommend this hotel. The rooms were quite
small and do not have individual controls for the air conditioning. Well, that last
part isn't true. They do have controls mounted on the wall. The controls don't actually
do anything. You have to tell the owner if you want the air turned on and he flips
a switch in a locked room. That switch controls all a/c for all rooms, whether they
want it or not.
Wednesday started out with a six mile climb out of Williamstown, MA over the border
into Vermont. I left the main highway and took some backroads over the mountain
and down into Bennington, VT. The objective today was to see and photograph three
The Bennington Covered Bridge Loop is 41.8 miles with 2573 feet of climbing. Here's
the route: http://ridewithgps.com/routes/224629
Bennington, VT turned out to be a charming little mountain town with lots of old
buildings and a pretty downtown area.
The stories about the road closings were accurate. Some of the roads were closed...
but I figured that was meant for other people so I went on through, anyway. ;-)
I made it to all three covered bridges on this route. All three of them had orange
cones and "Road Closed" signs blocking the entrance, along with huge concrete blocks.
For photographic purposes, I moved the cones and signs to the side, took the photos,
and then moved them back in place. Except at the Paper Mill bridge. People were
watching so I just turned the sign sideways so the edge was toward the camera and
then carefully positioned some wildflowers to block the distracting elements.
Some roads had been washed out but I was able to get around all of it and only had
to dismount and walk once for about 200 yards. Piece of cake. :-)
Thursday morning, the final ride day, was warm enough in Williamstown that I didn't
need a jacket when starting the ride. Here's the route: http://ridewithgps.com/routes/228799.
This is 47.1 miles and only involves 1953 feet of climbing.
A quick ride over to North Adams, down into Adams, and catch the Rails to Trails
down to Pittsfield.
Rails to Trails are projects that take old, unused railroad lines, remove the tracks,
pave over the path, and usually put in nice landscaping, benches, rest areas, etc.
This was an 11 mile route that followed the Hoosic River and the border of a large
lake. Great ride! Well worth doing.
I hit the northeast side of Stockbridge right at noon and decided to find some lunch.
A two cheeseburger meal sounded great so I punched McDonalds into the navigation
software and found one only .8 miles away. When I arrived, it turned out to be an
interstate rest plaza with no direct access from the road I was on. However, there
was a walk through gate in the fence so I rode through and was soon munching on
Outside the restaurant, gearing up to continue the ride, some guy stopped and said,
"They don't let you ride that on the interstate, do they?"
I responded with, "No, even I can't do that and I'm the Lieutenant Governor."
He looked at me, blinked a couple of times, and then walked off. Most people have
no idea who their Lt Gov is, anyway. LOL. Eight miles later, I was back at the Days
One of the things I learned on this trip was to watch the shadows when on backroads.
The main roads are generally in good repair but the side roads aren't as reliable.
It took a while but I finally figured it out. The sections of side road that are
in the sunlight, meaning they pass through clearings, are typically pretty smooth.
The sections that are in the shade of trees don't get direct sunlight in the winter
time to melt the snow and ice so it just sits there, eroding the pavement. The pavement
that passed through shady areas very often was broken up, had deep cracks or potholes,
and riding over them was enough to jar your fillings loose. Best to stay on the
high side of the road, when possible.
Stick a fork in me, Alice, for I am done! Three states, five days, 234 miles, 10,300
calories burned (which is way, WAY under the true value because that calorie counter
doesn't take into consideration the monstrous uphill grades that I climbed.) and
lots and lots of great memories and photos.
- Have your bike serviced before leaving home. Make sure your tires are up to a lengthy
road trip. Might be a good idea to have your local bike shop check your fitting,
too. That way you'll be delivering maximum power on each pedal stroke.
- A bike with a triple chain ring (front gears). If you're one of those macho types
that puts your chain on the big ring on the front and "powers up" the hills around
your house, you're not going to make it up these mountains.
- Hiking shoes of some sort for Bash Bish Falls. This is also the only time you will
need them on this tour.
- If you're a photographer, consider bringing a travel tripod. It's the only way to
hold the camera steady enough for some of the slower speed shots of the falls.
- Bring a GPS navigation unit like a Garmin or something similar. Most of these routes
are quite remote and don't have cell coverage at all. GPS software on a smartphone
will be unable to reach a tower to acquire a data signal to draw the maps for you.
- Be nice. You're an ambassador for all cyclists when you're out on the road. Stay
to the side, when possible and safe, and share the lane with motorists. When a motorist
pulls up and stops at a side street or driveway and waits for you to pass safely,
give them a smile and a wave and say thanks (even if they can't hear you). It might
give them a good impression of cyclists and that impression might cause them to
give another cyclist a wide berth next time and save that rider's life.
Doing it yourself:
If you decide you would like to try this same tour, here are the mapped routes:
All of the maps have cue sheets that can be printed, the maps can be printed, or they can be downloaded to a GPS navigation device.
If you're considering a solo trip, you might find some useful information in the solo touring article:
Solo Touring 'How To' Guide