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Roundabout Brattleboro: a 3-day bikepacking trip in Vermont


It was 4th of July weekend, and we were itching (soon to be literally) to get outside and enjoy a mini bikepacking trip. With our interest growing in gravel riding (less cars, more trees please!), we turned to bikepacking.com for inspiration: i.e. the mecca for off-road multi-day trips. This is how we learned about the Roundabount Brattleboro route: a 2-3 day, 137 mile bike loop that starts and ends in Brattleboro, Vermont.


The website proclaimed well-maintained dirt roads and "woodsy doubletrack with some mud sections, ruts, and rocks here and there". By that definition, it didn't seem too complicated or technical! There were two main camping locations around mile 50 and 85, making for a long Day 1 and Day 3 and a shorter Day 2, and services were limited through the Green Mountain National Forest (mile 30-80, roughly). Overall, the route had a substantial amount of climbing in the first half, offering more downhill relief in the second half.


In the heat of July and with loaded bikes, the route was going to be work but we really looked forward to it!

Route from Bikepacking.com

Before beginning our ride, we drove the 4 hours to Brattleboro on July 3rd and arrived to town late at night. Conveniently, Fort Dummer State Park was nearby, and it had ample camping spots. At the entrance/ check-in, a map was posted on the after-hours window which indicated tent sites still available, circled in red. Score! We moseyed along in the dark down the quiet park roads and past all the other campers asleep for the night. We pitched our tent and had a great night sleep which was better than our original plan to sleep in the car in an unknown random spot in town.


Day 1: Brattleboro to Somerset Airfield camping

(54 miles, 5620 ft of grain, Strava map)


On the morning of the 4th of July, we left the campground and popped into Brattleboro for a quick bite at The Works Café. I was hoping for a great meal and coffee to kickstart the tour, and it seemed like this would be the place for just that–– they promoted sustainability everywhere and generally appeared down to earth with their farming aesthetic. But, it was incredibly underwhelming: everything was in take-out containers (which they said was due to the pandemic––a poor excuse now in 2024), and my eggs were cold. Boo. A rough dietary sendoff.


Outside of The Works, Brattleboro was immensely adorable with cute storefronts, artsy shops, and cafés. It reminded me a lot of Ithaca, NY where we were coming from, and I was excited to explore more of town when we returned back 3 days later.


We promptly went north to the Park & Ride where the tour began, avoiding the soon-to-be road closure for the upcoming parade on Main Street, and we assembled the bikes with everything we would need to camp out for two nights. We had hoped for a speedier preparation so that we could see some of the parade, but our sluggish packing had us catching the tail end of it. At least we were able to snag a picture with Uncle Sam!


The route for today was a sweeping U-shape, heading west from Brattleboro. We rode pavement for a few miles out of town, which was very cars-y as people left en masse from the festivities, and then the road converted to wide and sleepy gravel. Sleepy because the road was quiet (aside from song birds and buzzing insects), covered in wildflowers, and lacking any human activity besides ourselves. Yet, we were anything but––our energy expenditure was through the roof, and the hills felt relentless, each one higher than the last. Sometimes the grades were upwards of 15-19%. We were working so hard while progressing so slow, and, in the heat of the day, I stopped and walked a number of times. When doing so, the deer flies and mosquitoes would jump on the opportunity to feast.


One moment of joy came from a rare cyclist interaction. As we were ascending at a snail's pace, two women bombed down the hill. "Way to go. Don't give up. Keep going!" said one of the women in a very proud yet stern-like coaching manner. It really lifted our spirits!


After one marvelous descent, we popped into Halifax, a teeny town with a few cute and older buildings. Two days of the week (Thurs & Sat) , there is an ice cream truck that opens in town near the Community Hall, which we were sad to miss since it was Wednesday. Almost as good as ice cream, however, was a glorious hose on the side of the Community Hall building where we refilled our water bottles in a desperate attempt to keep up with the speed at which we were sweating it back out.


With it being a holiday weekend, we were concerned about businesses being closed and us being unable to get water. There were also limited services between mile 30-80, so we brought iodine tablets which worked really well anytime we passed a convenient stream (which was often). However, we also kept scoping for more hoses on public buildings and jumped at the opportunity when we had it (highly recommend this strategy).


Heads up riders: After another climb and descent to Jacksonville (which also has a cafe, but it had just closed before we arrived), there is a critical point in the online map which takes you to the west side of Harriman Reservoir. However, when we downloaded the GPX file and uploaded it to Komoot, Komoot refused to take us down that pathway, as if it didn't even recognize it as a road. We suspect this may be because it's private property (this is precisely where there is a No Trespassing area that other riders have just ignored). We didn't realize the deviation until we landed in Readsboro. Having experienced a lot of pavement and being suspicious that we were off route, we confirmed that Komoot gave us a roundabout way to get to the north end of the reservoir. So, double check your route to know if it is taking you along the reservoir!


As we troubleshooted at the Readsboro Inn, we confirmed that the rest of our route matched the original way. We were too far past the turnoff (and down a large hill) to consider backtracking. So, we enjoyed a cold drink and Wi-Fi to reenergize for the next segment. Pro tip: we were told that the inn here has a $30/night rate (needs fact checked), which was so tempting at 4 PM. But, with daylight burning, we pushed on to make it to our campsite for the night.


A consequence of our reroute were two additional pavement hills that were incredibly steep, and at this point, we were pretty beat. After the slow and steady climbs, we were rewarded with a relieving, and very speedy downhill that turned onto Somerset Rd, the homestretch of the finish line for the day. The difficult Day 1 ride had us seriously contemplating whether we could do the same thing again for the next two days, especially because rain and muddy singletrack were in the forecast.


The dirt road to our final destination hugged a slow and beautiful river, and as the sun was setting, it was incredibly tranquil. We rolled into the Somerset Airfield which is an open camping area where you take any open spot you can (bathrooms are present, so that's a plus). Many cars and trailers had backed into the narrow grassy strip, and dozens of people were barbeque-ing, playing country music, and celebrating the holiday as you would expect Americans to do. There were some available areas to pitch a small tent, but it was pretty crowded on the whole. At the very entrance to the airfield, there was a slight hill that went behind a thin treeline. Upon investigation, it opened to a larger, more secluded field with extra sites that were completely unoccupied, likely because you couldn't drive your car there, and it required you to walk 30 seconds. It was incredible!


We pitched our tent, hung up a clothesline, and rinsed off in the creek (which was in close walking distance). Not having to share the site with anyone was a huge plus since we could hear the loud music and fireworks in the distance for hours.


Even though it was a challenging day because of the elevation gain, rocky terrain, heat, and heavier load, the ride was very rewarding. And we achieved our personal record for most elevation climbed in a single ride!



Day 2: Somerset Airfield to Windhall Campground (ish)

(39 miles, 2379 ft of grain, Strava map)


With rain in the forecast for the afternoon, we woke up earlier and hit the trail while the rest of the campground slowly began to stir. The hope was that we would get any gnarly terrain finished before the deluge (fingers crossed).


Within the first 3 miles, we crept up behind two other cyclists who appeared to be bikepacking the same route. And it was confirmed––William and Mikayla had traveled here from Boston to bike the Roundabout, and we didn't yet realize that we would continue biking with them for the remainder of this day and the following. Immediately, it was easy to connect with them as they are experienced bikepackers who completed the Great Divide (on my short list to ride!) and other tours in the United States and internationally. William and I also followed similar career path trajectories which made for an exciting discovery when we could bond about ticks and vector-borne diseases.


One fascinating point of interest that we crossed early on (about 5 miles into the ride for the day) was a cool, abandoned blue bus that was riddled with bullet holes– a kind of Into the Wild-like aesthetic. It was pretty torn up on the inside and was strewn with beer cans––clearly a teenager hangout spot.


Now a group of four, we powered through the slow climbs and rocky descents through the Green Mountain National Forest. It was only about a third of the elevation gain as the previous day, but I was wrong to think that it was going to be a piece of cake. My least favorite part of the day was honestly the downhill, which is crazy to say after the relentless uphills of yesterday. The downhills were so chunky that they begged for bikes with suspension. On our rigid frames with racks, everything jostled and rattled, including my bones and brains. Not to mention, only 20% of my brakes were actually working (my bad), and it made for painfully fatigued hands from clutching the brakes on the precarious descents. There were also deep ruts which would periodically catch my front wheel and make me lose my balance. I had fallen twice.


During this MTB escapade, the skies also opened up and unloaded raindrops as chunky and fat as the boulders I was narrowly missing. They really were impressively massive droplets that felt refreshing and kept the bugs at bay; however, the rocks became more slippery and precarious than before, and the ruts became softer and muddier. It was so physically and mentally tiring.


After what felt like way too long, we popped onto a manageable gravel road again, and I felt instant relief. The clanging and rattling of the bikes shifted to peacefulness and stillness, except for the hum of happy chains churning. We rode pleasant downhills to Bondville where we enjoyed a market with fresh food and cold drinks before finishing the ride a few miles later at Windhall Campground.


So, a note about the Windhall Campground: it had undergone serious flooding last year and it blew out some of the infrastructure. Consequently, it became closed indefinitely. Uri and I didn't know that because we are irresponsible and didn't look into the sleeping arrangements at all, but William and Mikayla did. They suggested that we might not be able to actually camp there, but we (all four of us) were going to try anyway. And I'm glad we did because the campground was epic: there were gorgeous lean-tos, a swimming hole under the bridge, and beautiful views. We enjoyed laying in our hammock and swimming in the river, rinsing off the caked grime from the muddy trails, rain shower, and endless sweat. A truly relaxing way to end the day.


Around 8 PM, we started to settle in for the night, us in one lean-to and William and Mikayla in another lean-to, when a golf cart buzzed by. We knew what was happening immediately. An older couple promptly and coldly told us to leave, while having no suggestions for other places to camp. They just as quickly zipped away again.


We knew we were in the wrong for being there (though there technically weren't any signs at all where we arrived). If anything, we were annoyed they waited until dusk to kick us out. But, we packed up again and biked another 2 miles or so until we were officially out of the park, and we pitched our tents on a wide, mowed grassy area. Fireflies buzzed around and an owl called out.


All was well.



Day 3: Windhall Campground to Brattleboro finish

(51 miles, 2533 ft of grain, Strava map)


Our alarms went off early, around 6 AM, and we all efficiently packed up camp (William and Mikayla more speedily than us, which encouraged us to not lounge around). We didn't get rained on at night, surprisingly, but the morning forecast looked VERY wet. And soon enough, we were peleton pedaling in the warm summer rain shower. As usual, on days when I am wary about the conditions, I end up having the most enjoyable time. We also had glorious downhills that would normally be extremely pleasant, but with my handlebar bag broken and no longer protecting me from road backsplash, I was receiving a Jackson Pollock mud facial at 25 mph, rotating which eyeball I was squinting out of to see.


Unfortunately, we were too quick with packing up camp, and so we missed the opening hours for a recommended cafe in South Londonderry historic district. But, by mile 17, we made it to Grafton, and I was effectively splattered with mud and positively soaked. The small grocery store/ café beckoned us regardless of our appearances, and we indulged in drip coffee and delicious breakfast sandwiches. It is so positively satisfying to arrive to a place feeling completely worked and disgusting and being rewarded with delectable treats. It's almost the reason why I do this!


Post-Grafton, we had our last large climb for the day which was on the muddiest section of the trail yet. Deep pits of muddy water and ruts peppered the trail, along with more steep boulder-y downhills. At one point, I did walk my bike through a boulder mine field which was impossible for me to bike (William's fatter tires and Mikayla's suspension had them zooming, seemingly effortless, across the terrain). The trail was wide though, compared to the day before with weedy singletrack and hidden rocks. I still white-knuckled my barely functional brakes, but ultimately had a grand time today!


Then, we finally spotted it–– the rope swing! On the website, it promised a rope swing and swimming hole, and we were on the lookout for it the past two days. We were beginning to think we had been lied to when, 15 miles shy of Brattleboro, we hard braked at an opening in the trees. The long, knotted swing hung limply from the rafters, begging to be used. With some mild regret, we couldn't muster the courage to do it, dissuaded by the rocky bottom and fears of coming up short. But we swam in the deep and lazy river, and it was so refreshing and magical. I only wish we could have stayed longer.


The rest of the ride back to Brattleboro was net downhill and speedy, first on paved roads and then on a stunning, compact dirt trail when we entered town. To our delight, there was another rope swing! We were tempted to swim again, but we were so close to the finish line (and ice cream!) that we pushed on. So many people were outside recreating, and the air was so light and full of enjoyment that cruising to the end was an absolute pleasure.


Then, we made it! Ending back at the Park & Ride, we loaded the car with all of the rank, wet, and disgusting bags and clothes that we created in the last three days. We exchanged contact with William and Mikayla and split ways––hopefully to ride again together another day?


Back downtown to walk around and explore more, Uri and I celebrated with giant ice cream cones (Vermont maple flavored for me, YUM) and Thai iced tea before heading back home to NY.


Another solid weekend warrior trip!


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