October Summer

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October, 2019

As summer weather begins to cool off and autumn sets in, I’m settling back into work life in Williamstown.

It’s my third fall here in the Berkshires, and I can’t think of a more beautiful place to spend this time of year. Cool misty mornings that crest into warm afternoons before tapering off again as evening sets in. And the foliage! The colors tend to begin to turn toward the end of September, and the sweet spot follows quickly and only lasts a couple of short - and spectacular - weeks. 

In early September, a friend of mine, Magnus, took me on a bike ride that I think has changed my perspective on riding forever. Before this past summer, I’d really only ridden on paved roads. My two stints of bikepacking with Matt introduced me to the world of off road riding, although I was under the impression that in order to do that kind of riding, a mountain bike was required. It was Magnus that facilitated the opening up of an entirely new world to me.

I had always been one to plan out specific local loops to ride, and then ride those same loops over and over. I had 3 or 4 solid routes ingrained in my head that I’d rotate between, and that was it. One particular afternoon I was riding with Magnus along one of these routes. As we rounded the farthest part of the loop and began making our way back home, I can explicitly remember Magnus, riding ahead of me, looking over his shoulder and saying ‘I have a surprise for you. Follow me.’ Magnus had grown up in Williamstown and was also an avid rider - I absolutely trusted his local knowledge and was excited to see where we may end up.

Magnus turned right onto a hard packed gravel road that I’d passed by dozens of times without a second thought. Oh boy. I had always been convinced that my road bike, with narrow little tires, would pop a flat instantly on any non-paved surface. Turns out, bikes are capable of more than I gave them credit for. I followed Magnus deeper into the forested area as the road slowly began to slope downward. Magnus, on a bike designed for gravel with wider tires, was well ahead of me, riding comfortably. I, on the other hand, was laser focused on the road directly in front of my front wheel, holding on to the handlebars for dear life as I did my best to not lose control while avoiding as many tiny rocks as I could. After a couple of minutes, I gained confidence in the fact that my tires could indeed handle this bumpy terrain. I loosened my vice-like grip on my handlebars and finally looked up to take in our surroundings. By golly, I was blown away.

The trees had given way to an expansive view of the Taconic Range along the VT/NY border. Our dirt road curved down a sloping hillside, where a single house stood overlooking dozens of acres of open fields. There was not a single person or car to be seen. I gawked at the world before me as I coasted after Magnus, finally coming to a stop when we met up with the main road again. In all, it was probably less than a mile of dirt road. I could not believe that this road existed so close to where I lived for going on three years, and it had been a secret to me until today. I was on cloud 9 the entire rest of the way home, incessantly describing and re-describing how I’d felt and what I’d seen. Magnus laughed along, glad to have made such an impact.

Magnus’ surprise dirt road, although from a later ride…it’s become a favorite of mine.

Magnus’ surprise dirt road, although from a later ride…it’s become a favorite of mine.

How many other roads like this had I been missing out on, right in my backyard? I could feel my mindset changing. I feel like I now truly understand how a bike could - should - be used as a means for exploration. The routes I’d followed from Bikepacking.com were an excellent resource, but I now wanted to explore on my own.


A couple weeks after that ride with Magnus, the foliage now peaking, I rallied two friends to get out for a ride over the long weekend of Indigenous People’s day.

Chris, Colin and I had been bouncing the idea around of getting out on part of the Vermont Gravel Growler route for a couple of weeks, but had yet to take any action steps. It wasn’t until the Friday afternoon before the long weekend that plans finally came to fruition. The weekend forecast in Vermont was 60s and sunny. We had a window, and I knew we had to take it.

I called them both from the car on that Friday afternoon on the way home from a work trip. After 30 minutes coordinating the logistics, I got home to pack up the bike before an early Saturday morning drive up north into the Green Mountain State. Our meeting spot? Hill Farmstead Brewery, exactly where Matt and I had started our first ever bikepacking adventure just a few short months ago. This time, the three of us, and a third friend, Jackson, would follow the southern part of the loop toward Burlington for two full days and one night….what I’d soon learn to call your classic bikepacking ‘overnighter.’

Hazy IPA’s from Hill Farmstead Brewery, VT

Hazy IPA’s from Hill Farmstead Brewery, VT

Chris & Jackson bad already arrived to Hill Farmstead by the time Colin and I rolled in, and kindly had beers already ordered for us. We sipped and packed up the bikes for an hour or so before saddling up for 38 glorious afternoon miles in the sun. The trees displayed the entire spectrum of yellows, reds, and oranges - the colors more pronounced with the deep blue sky as a backdrop. As the afternoon light began to fade in our final few miles, we rolled downhill on flowy singletrack into Montpelier, the destination for the evening. We rolled up to Three Penny Tavern just as darkness set in and sat for a couple hours enjoying burgers and local craft beers, our steeds waiting patiently for us outside. We said goodbye to Jackson, who could only join us for the day and had stashed his car in town, then Chris, Colin and I set off to look for a place to sleep. 

Chris, an experienced adventurer himself who has explored the Rockies, the Alps, and the Andes on two wheels, led us through the art of stealth camping...pitching a tent in a place where it may or not be completely legal to do so. The trick is to get there after dark, and then wake up early enough to pack up the evidence of your overnight experience before anyone else shows up. Tonight, that place was a community field near the center of town. We tucked in as far to one side as we could, crossed our fingers, and settled in.

If I could spend every day of my life cycling through Vermont’s back roads, I would. The exhilaration of a long climb into the mountains, followed by the rush of the inevitable downhill on the other side, only to pop out into another quintessential New England town to stop for a beer and some food at the local spot...there’s nothing better. Those beers and that grub feels oh so earned at the end of each day, because they ARE earned, dog gone it! 

Cruising.

Cruising.

We woke up to a cool, misty morning - the only sounds a light breeze and the birds chirping. Tents were packed up quickly before diving into a quick breakfast of gas station burritos that we’d purchased the night before. As we rolled out of camp, the temperature was already in the 60s. As we cruised through Montpelier, we almost immediately passed a little cafe with folks enjoying breakfast outside on a patio. The three of us looked at one another, already knowing that we were all on the same page. We stopped and had a second breakfast. Bikepacking is the best.

Good morning gas station breakfast burritos.

Good morning gas station breakfast burritos.

Three loaded bicycles & three humans in one tiny SUV. Proof that is possible.Click Here for the Strava route from day two.

Three loaded bicycles & three humans in one tiny SUV. Proof that is possible.

Click Here for the Strava route from day two.

With extra full stomachs, we climbed out of Montpelier and were soon back gliding along Vermont’s back roads. We stopped in the tiny town of Northfield for beers and snacks at Good Measure brewery, and then continued along old forest roads and singletrack, rolling over carpets of red, yellow, and orange leaves before popping out of the woods and into Warren - our final destination. Before loading three bikes and three people into Colin’s awaiting car, we refueled on food from Mad Taco and outdoor beers in Lawson brewery’s beer garden. By nightfall, we’d made the drive back up to Hill Farmstead to retrieve Chris & my cars. After goodbyes, we were headed our separate ways home. 

One quick afternoon of prep had led to two perfect days on the bike. I feel that there is a common notion that for a vacation to be worth it, one needs to make it an extended break. While there is no arguing that extended time away from one’s day to day life is refreshing, I’d argue that escaping even for just an overnight can make one feel like they’ve gone and experienced something entirely different. And that can often be enough. After this adventure, I have a new appreciation for the ‘overnight’ and will aim to make these short stints away happen more often!

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A First Race

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Montana. And Hitchhiking on Craigslist