There isn’t a huge cycling scene in Springfield, MA, so most of my rides are done solo or with Morgan except for the rare occasion where I meet up with one of the few friends I have who ride. My friend Mike and I went on a couple casual spins during the early days of the pandemic, but for some reason getting out together hasn’t been top of mind for either of us lately.
With plans to head out to the hilltowns for a repeat of a nice remote loop Morgan and I had done last year, I thought of Mike and he happened to be available. Mike owns a hardtail and my most offroad-capable bike is a gravel bike, and this route does a great job of meeting in the middle.
After parking at the Knightville Dam, we left the lot and almost immediately hit the first uphill of the day. This tarmac appetizer of three-quarters of a mile at 5% was just enough to warm us up on a chilly autumn morning, and then we dipped under a gate and took a gravel access road down into the reservoir basin.
This ride is pretty unique because according to some maps the route is underwater. The Knightville Dam was built to control potential flood waters for communities downriver and access fluctuates based on snowmelt and rain. You can read more about the project here. When we were there today, there was a ton of brush and other debris in piles near the dam, presumably washed down during the massive flooding that made headlines in Vermont recently. Even with a rainy few weeks, the worst we had to deal with was a bit of mud where we turned down towards the dam.





We spent the first part of this section of the ride side-by-side on nice doubletrack, but moved to single file as the surface became narrower and rougher. Because this area is often underwater no trees can survive, which lends to beautiful panoramic views the entire time. This section of our planned route was only four miles long, but we kept the pace light and stopped a bunch to chat and check out the scenery.
Eventually we turned onto a side trail that intersects the river we had been riding along the past half hour. There’s no bridge to continue across to the other side of the trail – you have to get a little wet. When Morgan and I had been here before, wading through a river wasn’t part of our original itinerary, but it was low and slow and the day had air temps around 70°F so we decided to push our adventure a bit.
Ironically, this time when the river crossing was part of the actual plan, it was so much worse. The current was so strong that we struggled to keep our bikes from washing away downstream and well past our knees most of the time. There were a couple spots that I had to move left or right to avoid plunging in past my waist. We had to tackle these setbacks while also dealing with water that was no warmer than 45°F. Before I was halfway across, I had no feeling in my toes, which was almost preferable to the pain. Mike’s guess was it took us about two minutes to get across, but it felt like a lifetime.


Mike was a good sport through all of this. I know I wouldn’t have been super happy if somebody told me to do this in the spirit of fun. Luckily for me, Mike is a psycho and has a cold water plunge tank in his basement, which probably makes him better suited for our excursion’s climax than anyone else I know.
After putting shoes back on and clipping in, we did a lap around the Indian Hollow Campground. Closed for the season at this point, it stands uniquely as the only federal campground in the state outside of a few on the Cape.
Our feet were just beginning to thaw out at this point, but we sped up the recovery process with our longest and hardest climb of the day. Four miles even at 4% doesn’t sound awful, but the first mile and change averaging over 10% uphill on a narrow dirt road made the (relatively) tame remaining portion hurt a lot more. On the bright side, the pain in our legs and lungs fully replaced the pain in our toes, and by the time we struggled to the top we had full circulation back below the knee.



Feeling accomplished and with spirits high, we rolled into the quaint Chesterfield town center, hit a couple sick jumps at its small skatepark, and sat down at the Chesterfield General Store for lunch.




It’s a shame the Chesterfield General Store is so remote, but it’s probably a good thing for my wallet – all of the food here is incredible, with great sandwiches on the menu and a wild variety of baked goods made in-house. I route a stop here into every ride possible. We did sandwiches, apple crisp bars, beers, and espresso drinks. I really felt like I should’ve been buying with the questionable judgment on our route, but Mike treated me this time. Very grateful.




The store is super friendly to cyclists, with a bike in their logo, a wicked cool Mont Ventoux poster dominating the seating area, and lots of small bike-related tchotchkes sprinkled throughout. As we were leaving we ran into some folks riding mostly off-road from Cheshire to Deerfield for the cyclocross race at Treehouse, which sounds like an awesome day on the bike.
After leaving lunch we hit our fastest descent of the day, two miles of smooth tarmac downhill at 6% with the last mile ramping up to 12%. Climbing is meditative, but ripping downhill at 45mph is just pure fun.


We had one final challenge before our final descent to the car, with two miles at 5% ahead with the first half clocking in at 8% and some punchy bits over 10%. With a fair amount of climbing in our legs already, this would’ve probably felt tough if it wasn’t for the carbs, coffee, and beer powering us up. We spun a low gear and pushed our way to the top before the final descent.
I always love the feeling of ending a good day in the saddle with a long descent, and over seven miles of mostly downhill was just what the doctor ordered. We pushed a high gear, laughed, stretched, talked about how the river wasn’t really that bad, and made the intention to get out again soon.


I’m a firm believer that the best way to explore the world is on two wheels; walking just isn’t fast enough to see everything I want to experience in this life, and cars will destroy the world before I get to everything. On a bike, you move through the world on a human scale and under your own power, with the ability to go anywhere your legs will take you. The physical and emotional joy of riding is almost secondary to the freedom cycling brings.
Today was nothing special or groundbreaking, just a regular day doing something fun with good company.