It’s called the bay state, but not all if it is by the bay. In fact most of it isn’t and this trip comprised of 0% bay as I headed inland from my parents house in Sharon, MA accross the apalacians to Albany, New York.
The picture above probably encapsulates the height of the beauty I’ve encountered in Massachusetts while passing by the beautiful Mt. Sugarloaf in Sunderland, MA.
This journey was a long weekend trip that meant to seal the deal with my 2016 cross country trip that started by Albany, NY and ended at the Pacific ocean. Although I had biked accross the majority of the United states, I had felt a bit dishonest telling people I biked across the whole country since I skipped a major part of it, the appalacian mountain range.
My choice to skip this part of the country was intentional back in ‘16 as it was still April in New England, I was embarking on by first solo bike tour, and didn’t want to come crying home with my tail in between my legs because I had bit off more than I could chew in tackling a mountain range in the cold by myself. In 2016 I had taken a greyhound bus to get myself over the subtle but non-trivial mountain range known as the appalacians to get to Albany and take the flat and gentle erie canal trail on my way west.
As I would find out as this weekend trip progressed, my decision to skip over these mountains 5 years back was smart as I discovered that the mountains were no joke.
Anyways, I started my trip from Sharon, MA which is a little town just south of Boston. Day 1 was a somewhat gentle start to the trip. I want to say it was about 70 miles or so with some gentle rollers for most of the day. Towards the end of my trip I passed by a town called Sturbridge. Ironically this is the start of the famous pan mass challenge, a popular charity rides that “traverses” the state” although the town is not even in the center of the state and the ride completely avoid the most challenging riding in the state. They should probably rename this to the half pan mass challenge or pan mass semi challenge.
Anyways I settled down on my first night in a little campground called Quinebaug Cove Campground, in Brimfield, MA. They had some snacks and such that I could use to help myself refuel but had to also order delivery from a local pizza + grill place in order to fill myself up.
The next day was a bit more challenging. I started off riding through Palmer MA which I remember slightly from a Jewish retreat I went on in my early childhood. By the time you get out to this far west in the state, you really do start to notice a change in pace of life out here and start to feel a bit of that country vibe. As I headed up through Belchertown I stumbled across a beautiful bike trail leading me into a liberal haven into what was started to become more country, Amherst MA home of the University of Massachusetts.
I was impressed by the quality of the bike path and even tempted to ride it longer into the Northhampton area but my route dictated that I continue riding more north to get to the Mohawk Trail. As I continued North I passed by some beautiful hills starting to look more like mountains as the cover photo for this post.
There becomes a point in many bike tours when you think to yourself, “Wow can’t believe a place like this exists so close to me.” Seemed to me like a hidden gem in the state and makes you fortunate to have access to such a beautiful land.
So I continued up north and eventually after some substantial climbing (by Massachusetts standards) made my way to a little town called Shelburne Falls.

This was another one of those cool places that you didn’t realize existed so close to you. Was a nice little town with some picturesque waterfalls along the Deerfield river. Seemed like there were some cool museums and historical things there as I believe this was a pretty central place for native americans. However I’m not going to pretend like I’m a historian and tell you all these facts about the place so I’d recommend just going there and seeing for yourself if you’d like to learn more.
I settled down at a place called Country Aire Campground where I cooked some food for myself over an open fire for the first time. Definitely burned a bit of meat at there’s no knob to turn down the heat on an open flame and didn’t quite want to endure a 3rd degree burn by picking up a burning piece of wood with my bare hand and placing it on the side. However some of the food was cooked to perfection so I can’t say I f’ed up all the way.
There was a dude with a Tesla at the Campground. I was wondering how he went about charging in a rural area like we were in and realized that campgrounds have electricity so you can just charge like you would use an electric hookup for an RV. Briliant idea and not exactly rocket science.
The next day was my biggest day of climbing where I traversed the rest of the Mohawk trail and made myself to yet another liberal hostspot called Williamstown, MA home of Williams College, a liberal arts university in the heart of the Berkshires.
Along the way to Williamstown I passed by some nice lookout points including a place that called itself “America’s Switzerland”


Calling itself America’s Switzerland is a bit of a stretch, however it was beautiful spot.
As a decended into town I passed over the appalacian trail and did see a handful a hikers coming through town. I ended up staying in motel in Williamstown where it was nice to enjoy the amenties of a roof, bed, place to wash and dry my belongings, my own shower, etc. Sometimes you got to camp a couple nights in order to truly appreciate having a roof over your head.
The next day of riding would be my last of the trip. I did a good amount of climbing the next day as the ride from MA to NY passing over the “Taconic Ridge” as would definitly classify as mountains rather than hills.
Overall was beautiful to see more of my home state and truly complete the journey I had originally set out on several years past.

As I made my way to the albany train station to take the amtrak back to Framingham where my brother was kind enough to pick me up, I stopped at the exact spot on the hudson river that I had remember taking a picture at when I was embarking 5 years ago. As I stood in that same spot, I remembered feeling of excitement, adventure, andoverwhelming sense of freedom and gratitute do be able to embark on such a trip.
Having completed this journey had marked two full traversals of the US.
So in other words, time for a third.