A Short Motorcycle Ride Around the Mass/Conn/NY Border
By Greg B. It’s not often that I get out much, something I can write as an official ‘travel’ article for this website! But I decided to branch out, and qualify motorcycle trips as travel. The first few write ups will be me practicing how to write these articles for a longer, multi-series write up about the trip my father and I took across the country on our motorcycles. But a few weeks ago I got the chance to go home, and had a nice break in the weather (well, it started out that way), and got a good long 5.5hr ride in with my father.
Part of the reason we were excited to take this trip was my father had just bought another new motorcycle, a kawasaki 1600 nomad. Now, this is a BIG bike (1600 cc, as you might have guessed!) and I therefore was able to upgrade from the 1984 Honda Magna, 750cc to a Kawasaki Vulcan, 750cc. For me, the bike sits a little lower, and the bars are a little higher, but it’s still a nice smooth ride, with a lot of pickup! My father was taking his new bike out and we were just tooling around NY, riding random side roads to get out and get some riding time. The weather, while being substantially warmer down here in Baltimore (later in the day I returned to Baltimore, and it was about 20 degrees F hotter than NY!) and while it was warm in the sun in NY, it was certainly chilly on the bike! I was very glad to have left my liner in my jacket.
As you can see from the meandering image above, this trip really kinda took us all over the place. Initially, we headed north, taking as many back roads as we could that went or seemed to go in the direction we wanted to day. We were in no real hurry to get anywhere, with just a vague concept that at some point in the afternoon, I was heading back to Baltimore. Starting from Verbank, we took some back roads to get to Millbrook, just to get me warmed up and refreshed on riding a motorcycle, as it had been a good year and a half since the last time I rode! Everything comes back very quick though, and this new bike was a lot easier to find neutral in than the Magna. It was also the first time I rode with a windshield, and personally, the jury is still out on this for me. I don’t mind being beaten by the wind while riding, but this probably made the ride a lot warmer and more tolerable, given the 55F temperature, and growing cloud cover! My only issue with the windshield was that on curves, the tip of the shield was right about as far ahead in the turn as I want to look, so it gave me a weird light/refraction thing between air and windshield. I bet if it was raised a few inches, it would be a better ride, but that still remains to be seen.
So from Millbrook, we rode through town, then some sideroads to the north of the town until we came across the Shunpike, a road going east/west that connects rt 82 and rt 44 I believe. We took this to rt 82 and headed north through Standfordville, stopping at a Stewart’s along the way to grab coffee and something you cant get in Baltimore even at a deli (if you can find a deli)…. a hard roll with butter. From here, we continued north to Pine Plains, turned right on 199, then hopped off this road to some more side roads until we came across Rt 22. This road travels north/south right along the Connecticut and massachusetts border, so we headed north, with the intent on cutting across into Connecticut and shooting back down south. But, as usually happens, things on a motorcycle tend to be a bit more difficult than imagined.
Heading up North, we first topped on the side of the road to plan our route a bit, but were looking at the mountains of Boston Corners. My father was telling me about the history of this area, apparently back in the prohibition era, it was a favorite hideout of rum runners and gangsters, even to the point where it was too dangerous for either NY or CT to really go in and clean out, so they just left the area alone! Reading the above wikipedia entry shows that this area had been, for a long time, isolated and a refuge for criminals. From here, we headed north and took a right turn, a road which we thought would be an easy pass through the mountains at the border or CT/NY. It turns out, we were headed to Bash Bish falls, a nice little park with, yes, a waterfall. We had done a little hiking here in the boy scouts years back, but now we continued on the road up above the park. Finally at the top, we stopped for a rest and to check out this lookout point, which gave a spectacular view. You could see, from the top of this mountain, clear across NY state to the Hudson valley, the Hudson river, and across the river all the way to the Catskills, poking out of the horizon. While the view was beautiful, we had to continue on our way and find our way back. The trip was just about to get really interesting.
We continued heading east up the remainder of the mountain, then came to a “T” intersection. We made the assumption that by going right (south), we would come across some larger roads and get back. However, as we had continued up this mountain, the road became steadily in more disrepair, smaller, weather worn. But, we went south. About .5 miles down the road, the ‘nice’ blacktop gave way to very old blacktop, which within a few yards gave way to packed dirt. Now, this was my first time riding on dirt, except for maybe some dirt/gravel areas for very short periods of time in the cross country trip. But this packed dirt gave way to looser dirt, as we continued down the road, and finally became a slightly muddy, packed, and wheel rutted road that was windy and uphill. After 3 miles of this, we came across a ‘road closed’ sign, and had to turn back! It was 3 miles in, and 3 miles out and i swear, this was 6 miles of the most intense riding I’ve ever done. But, now out of the mud, we still have to find our way out of this mountain top! Passing a sign for Mt. Everett, I made a mental note to look up the roads we took. From google maps, it seems that maybe we had went south on “west st” after Bish Bash falls, towards Plantain pond, which is where the dirt road seemed to have ended anyway.
It turns out that if we had just made a left at the “T” intersection, eventually we would have found larger and larger roads and headed downhill, towards the town of Egremont and took rt 41 south towards Sharon. From here, we took 343 across the border back into NY and drove around Amenia for a bit, before taking rt up the mountain towards these two really long, uphill, sharp and fun curves. Once at the top, you are rewarded with a beautiful view of the valley below, and it’s certainly one of my favorite drives/rides around home. After climbing out of the valley, we rode around for a bit on the mainroad before riding off and messing around on some more side roads (including another dirt road! But this was a much shorter and easier ride) and coming out on the road West of Millbrook. It was around 2pm, so we continued into town, then took 82 back towards home in Verbank.
It was a chilly day for a ride, but it was a very fun ride. I find that when out on the motorcycle, you don’t need to go looking for adventures and fun stories, they find you. From the always twisty and fun to ride side roads, to getting ‘lost’ in the mountains with an amazing view of NY’s great landscapes, to just being outside for hours enjoying the road and everything in nature as you cruise by, riding has to be one of my favorite activities. Makes me want to get a bike down here in Maryland!

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Greg,
Sounds like you had a great time with your dad (you didn’t talk about that part of it). I’m not sure that “adventure found you” because you were riding, as much as because you were with your dad. In our youth – he would quite frequently lead us into similar adventures while on foot. Maybe it’s just the outdoors and exploring the beauty of God’s creation that does it. Anyway, glad you had a great ride.
By the way, bike riding in Maryland might not offer the magnificant views you had in New York/Conn/Mass as (in case you haven’t noteced) – Maryland doesn’t have many mountains … but it has lots of water. I just love that area with the Chesapeake and all those rivers running into it. Also, love (and miss) those crabs.