Hundred to Hambone

Moments before setting off on the longest ride of our lives.

Moments before setting off on the longest ride of our lives.

May, 2020

Since Matt and I confirmed we’d be hanging around Williamstown for the month of May in work limbo, waiting to see if Overland would run any trips for the summer, we knew we had to scratch our adventure itch.

We never seemed to plan anything too far in advance, so we figured we’d just continue to watch for particularly good weather and trust that something would come up to push us to take action. It didn’t take long for us to get the nudge that would spark us onto what would be the longest single ride of our lives.

Mt. Greylock Summit!

Mt. Greylock Summit!

Once we arrived back to Williamstown in the first couple days of May from our respective family homes, our time was spent almost entirely either on our bikes, planning bike rides, or sitting in the yard with a beer admiring a freshly washed bike. With no other commitments, we had the freedom to plan longer bike adventures for ourselves to explore new areas. Our first day back in Williamstown, our buddy Quinn joined us for a chilly 50 mile road ride loop up and over Mt. Greylock, our backyard monster of a climb that tops out just under 3,500 ft - the highest point in Massachusetts.

Pushing bikes up a dirt ‘road’.

Pushing bikes up a dirt ‘road’.

Over the next few days, we soaked in early May sunshine, more or less alternating between a short local rides and longer adventure rides. One particular doozy Matt and I won’t soon forget was a 60+ miler that involved a stint of pushing our bikes straight up a 20+% dirt ‘road’, and then a terrifying descent down the equally steep far side. Turns out not all roads that appeared on Strava’s route building platform were, in fact, navigable roads. Nor does it give you a great sense of how steep those roads might be. We were learning that a little more research before heading out on rides might be worth it…

On the second Sunday evening of May, we heard from a friend and former co-worker, Emily Hammel (or “Hambone”), that she was holed up alone at her childhood home in Warren, VT, finishing up masters degree classes from home. This was the nudge that Matt & I needed to fire up the ol’ bikepacking train again. It was over 100 miles up to Warren from Williamstown. Certainly doable in a couple of long days on the bike. But then, one of us had a brilliant idea. What if we could do it in one single day?

At the time, I had one ‘century’ ride of 100+ miles under my belt, which I’d done solo at the tail end of the previous summer. Matt had just completed his first century ride the previous month, at home on the flat roads of New Jersey. This endeavor would be, by far, each of our longest rides, and the ride with the most climbing - 131 miles, and nearly 11,000 feet of total climbing. Oh boy.

So, we picked that upcoming Thursday - just four days away - to go for it. The weather seemed promising, and Emily would have wrapped up her Master’s degree coursework that morning. We figured we’d spend at least Friday up in Warren (a day off after this surefire buttkicker of a ride seemed appropriate), and then figure out a way to make our way back to Williamstown. Matt and I would, again, be flying by the seat of our pants when it came to the return journey. This seemed to be our M.O.

Faster than we would have liked, it was the day before the ride. We spent the afternoon packing up all that we thought we might need, while thinking strategically about minimizing weight in our bike bags. This meant only packing two bags each - seatpost bag and backpack for Matt, seatpost bag and a newly-purchased Ortlieb frame bag for me. With limited storage space, sacrifices were made. Sleeping bags & tent, just in case? Na. Let’s force ourselves to finish the ride in one day, and perhaps we’d have to find a motel on the way back south. We’d figure it out.

Game day.

We awoke around 4am in anticipation of a 5am departure - we wanted to be rolling before light to give us as much daylight as possible. After a quick coffee and oatmeal, a recheck of the packed bikes, and the classic “I think I’m forgetting something as I walk out the door” internal debate, we were rolling into the still dark 35 degree morning. 

Necessary pause in the early morning sun to warm up.

Necessary pause in the early morning sun to warm up.

Probably should have gone with the thicker gloves. While our first 15 miles were a net uphill, which kept us warm, the next 15 miles were a net downhill...Matt and I agreed it was the coldest we’d ever been on a bike. All we could do was stop periodically to shove our hands in our armpits for a few minutes, and plead with the sun to get climb high enough to clear the hills and bask us in it’s warm glow. The promise of a 60 degree afternoon felt like a lifetime away.

By 11am or so, 6 hours in, we rolled down into the Vermont town of Rutland. We were about 80 miles in, ahead of where we thought we’d be, and feeling good. We texted Emily that we were 50 miles out, then grabbed some takeout burgers from 5Guys to enjoy in a park. Emily planned to leave her house soon - her plan was to ride 20 miles out to meet us at the top of Brandon Gap - one of Vermont’s notoriously steep mountain passes - where she’d then turn around and join us for our final 20 miles into Warren.

It was during this lunch break that we received confirmation from work that Overland would be cancelling all summer 2020 trips. While the writing had been on the wall for a while, it still felt surreal as it became reality. All of the work we’d put in all year long to build out those summer trips was for naught. That said, we were also excited at the prospect of a first free summer in years for either of us - how would we make use of that time? We weren’t sure, but we knew that biking would be a focal point.

Lunch Spot in Rutland, VT.

Lunch Spot in Rutland, VT.

We took our sweet, sweet time finishing those burgers and then hopped on the saddle again for part two. A dozen or so miles in, we began to climb. And climb. And then we climbed some more. Turned out, part of the reason we were able to knock off those first 80 miles at a good clip was because we’d saved the majority of our climbing for the afternoon. Ah, another lesson learned...plan your ride not just around the mileage, but also the climbs.

The climbing was relentless - steep, winding, and seemingly never ending. To add to the challenge, we’d unknowingly routed ourselves on pretty rugged dirt roads through the mountains in an effort to avoid highly trafficked roads, so even the brief downhill moments were slow going. We quickly realized that Emily might be waiting for us for quite a while at the top of Brandon gap. Without cell service, we had no way to give her the heads up, so we just kept plugging and chugging. 

Around 4pm, after a final big push up Brandon gap, we were relieved to find Emily patiently awaiting our arrival. Emily was more relieved to see us - she’d been up there waiting for nearly two hours and admitted she’d been considering coming down our side of the gap in a search and rescue mission. After a quick celebration at the peak, we ripped down the back side of Brandon gap toward Warren. Just before dusk, we rolled into Emily’s place. Route complete: nearly 11 hours of riding time, 131 miles, and 10,600 feet of climbing. Matt and I were over the moon, and also completely wiped. We ordered some takeout from Mad Taco, had a couple of Lawson’s Finest Liquids (read: beer), and hit the hay.

Friday was a welcomed slow moving day that started with a morning of outdoor pancakes & coffee, and a brief virtual graduation celebration for Emily in which I presented her a ‘diploma’ of the previous day’s newspaper. She then led us on a low stakes ride around the beautiful Warren countryside before we settled in for a rainy afternoon movie at home. Matt and I also had to plan out how the heck we wanted to get home…

Pre Ride Graduation Ceremony for Hambone.

Pre Ride Graduation Ceremony for Hambone.

The pieces seemed to just fall right into place. On Saturday morning, Emily was excited to drive us part of the way south, then join for part of that day’s ride. Nice to know we’d shave off at least a few miles that way! Emily also reminded us that we had a friend who had an empty family house near Stratton mountain, which was almost exactly halfway between Warren and Williamstown. After a few quick texts, we had confirmed a place for us to crash for Saturday night. The gamble to not bring sleeping gear had indeed been worth it!

Burger dinner atop Stratton.

Burger dinner atop Stratton.


With our legs already frustrated with us after our doozy of a ride northward, we did our best to minimize climbs and off road riding for the way home. No need to push the envelope. After saying goodbye to Emily about 25 miles into the day’s ride, Matt and I pushed onwards. Our only significant climb of the day would be up Stratton Mountain...turned out our friend’s house was quite near the top. Bummer that we’d have to climb up at the end of the day, but it meant Sunday morning would start with a rippa’ of a downhill! After trudging up Stratton mountain, Matt doing his best to hold off a newly discovered slow tire leak, bikes stuffed to the brim with both dinner and breakfast food, we settled in for the night.

We pushed for an early start the next morning in an effort to ensure we had enough time to make it home (no sleeping gear with us, remember?). The day started with a glorious descent down Stratton the way we’d come, and then 15 or so miles of winding around the mountain to find ourselves on the southern side. At that point, we hooked back up into the Green Mountain National Forest and turned onto what became our new favorite road - Forest Road 71. Twelve miles of slow rolling downhill in the middle of the Green Mountains. Tunes bumping from our portable speaker, our tired legs were thrilled to settle in for a half hour or so of bliss. We did not see a single other person or car the entire time. Moments like these are reminders of why all the uphill efforts are worth it. Every. Single. Time.

Forest Road 71 eventually came to an end, and we were back into familiar territory. The sun and our spirits were high as we finally made our way back into our driveway, 83 miles after departing Stratton. We met some friends at a local picnic spot for some outdoor takeout pizza to cap off a perfect day, and a perfect 4 days on the road.

We’d successfully pushed our bike boundaries once again. If you give yourself the entire day to ride, it turns out you can go pretty far. Duly noted. With a free summer ahead, I couldn’t wait to get into some adventure planning….on to the next!

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