Williamstown Overnighter

The Overland crew here in Williamstown threw together a relatively spur of the moment bikepacking overnighter atop the highest peak in the state, and I feel I need to document these 48 hours of pure joy.

Almost immediately after collectively learning that Overland would not be running in the summer of 2020, we in the office began to brainstorm ideas for one last outdoor (COVID safe!) group activity before we ultimately headed our separate ways. Matt and I, still riding high after our Hundred to Hambone adventure, suggested a bikepacking overnighter. While we all had camping experience (working for an outdoor adventure company will do that), only Matt and I had bikepacking / bike touring experience. Our friends, likely tired of hearing us rant and rave about our bikepacking exploits, were ready for an adventure of their own. They were in, and turned to the two of us to do the planning. 

While Matt took the lead in helping others figure out the right gear (Overland’s summer storage facility coming in CLUTCH with bike racks, panniers, and camping equipment), I dove into route planning. While I’d planned dozens of rides over the course of the past year, this was the first time I had an entire group - 7 of us - to consider. We needed something both logistically straightforward and at a physical challenge level that would be accommodating for all - not everyone had spent their spring biking as much as possible, as I had.

After spitballing ideas with Matt on where to go (tackle part of the route he and I had just done in Vermont? Ride a section of the Vermont Gravel Growler that we had done the previous summer?), we opted to create a new route - one that would start and end right in Williamstown and maximize time on as many of the spectacular roads in our area as possible. Where to camp? The Stony Ledge lean-to, of course. Two thirds of the way up Mt. Greylock and with a perfect view of the summit, Stony Ledge would also be a lovely place to enjoy a sunset. While we all knew that lean-to well, only a couple of us had ever spent a night there, and none of us had visited by bike. It would be the perfect Williamstown send-off.

Parking lot staging area.

A week or so after initially deciding on the idea, it was time to ride. We gathered in a town parking lot and divided up food & group gear as best we could. Burrito ingredients, camp stoves & fuel, and snacks galore. Sun was shining, spirits were high, and we were only two hours behind schedule. While Overland students & leaders couldn’t be out on any trips this summer, we as the full time staff were thrilled to feel the spirit of the Overland Summer, even if only for a couple days. With pots & pans dangling from bike bags & panniers stuffed to max capacity, we rolled out. 

Mid ride re-packing.

Over the next 38 miles that afternoon, we had the time of our lives. From the get go, Matt had tunes blasting from his portable speaker. As we rode, he would bounce from the font to the back of the group to ensure we all had our moments to sing along. A friend who wasn’t riding drove out to meet us about halfway through our ride...and surprised us with snacks, drinks, and popsicles! As we descended along bumpy gravel roads, rouge objects would occasionally come flying off of someone’s bike (or, in Emily’s case, nearly everything on her rear rack). We’d all stop, backtrack, then poke fun at the culprit as they picked up the gear, food, or clothing item, and struggle to reattach it. Securely packing a bike is hard. On one long descent, we ripped straight past our turn, and, much to everyone’s dismay, had to turn around and climb about a mile back up the road to get back on track.

Despite the occasional setback, attitudes stayed positive - how could they not? A small group of great friends, none of whom knew for sure what the next couple weeks & months of their lives would look like, riding bikes on a spectacularly summer feeling day in late May, in one of the most beautiful places we could have hoped to be.

Just before starting the late afternoon climb up Mt. Greylock, we pit stopped to pick up some beer to enjoy at camp. Exiting the stores, cold beers in hand, we immediately realized we didn’t have enough collective space on our bikes to store it all. So, we went with the only logical solution...tunes blasting, we cracked a couple brewskis to enjoy as we made the big climb up to camp!

Even with the late departure, leisurely riding, missed turn, and dilly dally stops through the afternoon, our arrival to the Stony Ledge lean-to coincided perfectly with the setting sun. Being a group with a wealth of outdoor experience and can-do attitudes, we soon split into teams for cooking, camp set up, and campfire making...but not before prioritizing a critical end-of-ride sunset beer. After enjoying a burrito dinner and watching the fire until it died out, we tucked into sleeping bags for the night - all of us fitting comfortably under the overhang of the lean-to.

While the rest of the group slept, Emily, Ben, and I awoke before dawn to sneak in a sunrise ride to the summit. While chilly early morning air made it challenging to forgo the comfort of our sleeping bags, we knew the push would be rewarded. Saddling up in all the layers we’d brought, we set off for the 4 mile climb to the highest point in the state. The world felt silent - as we pushed upward, the only sounds were our breathing and the occasional remark about the increasingly bright horizon. As we rounded the final s-turn toward the summit, the sun poked above the horizon, and daylight was upon us. The three of us spent a few silent minutes at the top, looking out eastward across the state. The purple mountains in the distance, the oranges and yellows in the sky, and the serenity that came with knowing we were the only three people to take in that view that morning made for an experience that I won’t soon forget. In all my years in Williamstown, it was my first sunrise from the summit of Greylock.

Sunrise at the Summit.

Second Breakfast.

After a chilly descent back to the lean-to, the three of us tucked in for another hour or so of sleep before the group awoke. We dawdled around camp as we enjoyed a breakfast of oatmeal and coffee. We couldn’t have asked for a better start to our day of riding - 7 miles down Greylock the way we had come, then immediately stopping at a lakeside Dunkin’ Donuts to enjoy a second breakfast. What followed was ten or so miles on the Ashuwillticook rail trail on the east side of Greylock, where we could glance up to our left to see the mountain’s summit, a reminder of how far we had come. 

Before we knew it, we were back in Williamstown. Our ride ended at Lickity Split - a Williamstown staple and unquestionably the best ice cream I’ve ever tasted. Enjoying our ice cream and basking in the midafternoon sun, we didn’t want the adventure to be over. And so, it wasn’t...we hopped back on the bikes and zipped over to a local swim spot on the river to cool off. Someone suggested ordering pizza and picking up beers to enjoy for an early dinner, and we didn’t hesitate to follow through. After a couple more hours, bellies full, the warm afternoon air began to taper off into a cool evening and we headed our respective ways home. Williamstown overnighter, complete.

I remember being hesitant about embarking on an adventure in our own backyard. Would it be worth it? Would we feel as satisfied as we might if we ventured farther from home? I feel that, as a society, when we plan vacations or getaways, we tend to believe that longer stints in faraway places are always more rewarding. After this quick local trip, I argue that there is immense value in taking the time to re-discover a place you know well and may take for granted. Taking this intentional step allows you to see your surroundings with a different perspective, creating a new experience for yourself that can help you find a new appreciation for where you live. Perhaps this feeling was amplified for us because we knew that our time together in Williamstown was coming to an end, but I think it would hold true regardless of that fact.

So, take the time to break the pattern of how you typically interact with a place. Hike that trail you love, but in the opposite direction. Take a night to camp out at that local campsite you’ve always been meaning to utilize. Bring dinner to that viewpoint in town. Ride that cruiser bike of yours through the streets you walk every day. Spice things up and find the new in the familiar!

Full route for the Williamstown Overnighter is shown below on RidewithGPS.