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: 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 strenuous.

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: Be prepared for 3174 feet of climbing and some spectacular scenery over the 48.6 miles.

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 the country.

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: 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 covered bridges.

The Bennington Covered Bridge Loop is 41.8 miles with 2573 feet of climbing. Here's the route:

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: 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 cheeseburgers.

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 Inn hotel.

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

Click here to open a slideshow of the images from this tour.