Southern Vermont Bike Tour

Meg and I just completed our longest self-supported bike tour yet: three days of dirt roads, singletrack, surprisingly nice Vermont corner stores, and Heady Topper. It was a lot of work, but such an incredible way to see small towns and forests across Vermont. There's so much out there that we've missed every time we've whizzed across the state in a car.

On bikes, it's so much easier to pull off to the side of the road to dip your toes in a beautiful stream, or engage in a staring contest with a deer or a porcupine, or debate eating a not-quite-ripe wild strawberry. You end up seeing an area through completely different eyes.

mandarb & sully mandarb and sully, at it again

Day 0: Littleton->Brattleboro (by car)

Our route began just north of Brattleboro, in Dummerston. Since we live a hundred miles away in Littleton, NH, we tossed the bikes onto our new 1up rack and made our way south to the starting point. As all good shirefolk do, we rise with the sun, which is like 4:50 AM near the solstice. So it was pretty easy to stop by the Blue Sparrow and enjoy our first fantastic Vermont foodie experience of the weekend -- two high quality breakfast sandwiches, a perfectly microfoamed latte, a just-a-tinge-sweet cold brew, and a croissant and scone for later consumption on the bikes. I am pleased to say that as fantastic as the Blue Sparrow is, it wasn't even the best breakfast we ate on the trip. More on that later.

With full stomachs ready to fuel a long bike ride, we parked the car at a park-and-ride by a covered bridge in Dummerston and set off over the covered bridge on our first dirt road of the trip. First destination: Brattleboro, a supremely touristy and surprisingly large Vermont town.

meg start ready to roll

Day 1: Brattleboro->Wilmington->Somerset Airfield

After our initial warmup on the relaxing dirt road, we ended up on a somewhat busy paved arterial into Brattleboro. Since it was a Thursday morning, traffic was light. Until we reached main street, which, in classic summer Vermont style, sows unending confusion among the Massachusetts tourists and backs up traffic for blocks and blocks. Fortunately when you're riding a bike you can just hop off it and walk down the sidewalk. Take that, car industrial complex!

meg climb it's the climb -miley cyrus

meg_park apple break time

Our next stop was a quick snack break at The Works. You know how your mother always told you that "if you don't have anything nice to say, don't say anything at all"? Well I don't have much to say about The Works. I certainly don't have anything to say about Meg's iced chai latte, which appeared to be made of a 1:1 sugar:water ratio. I damn sure don't have anything to say about my "latte", which literally had no foam at all on it and tasted like a 50/50 combination of day old burned coffee and overmicrowaved hazelnut creamer. I can say that our panini was passable, though inconsistently microwaved enough to both burn my mouth and still feature ice-cold sweet potato chunks. I can say that our bagel tasted kind of like the free leftover bagel you'd get after a board meeting at an insurance company.

brattleboro should have just gone to a brewery... never again "the works"

All I'll say is this... I do not recommend "The Works" in Brattleboro.

After our exciting food critic experience in Brattleboro, it wasn't long before we ended up back on windy dirt roads. Before long, those dirt roads started to go up an awful lot. But with our Blue Sparrow flaky-yet-soft-and-buttery croissant and delightfully-crumbly scone as fuel, we soldiered up the hills and generally enjoyed hanging out in the woods, saying hello to deer and porcupine, pointing out every tiny little cemetary on the route, and de-stressing from the pains of 9-5 life. There were so many stunning overlooks and cute houses on this section of the route, you should probably just look at the pictures.

salamander lil salamander friend

nate dirt nate gravel grindin' on some quality vt dirt

We stopped at a school in West Halifax to split an apple and refill our water bottles. And a nearby cemetary to finish the aforementioned insurance company board meeting bagel.

bagel bridge a great stop for a bagel

A short time later, our route took us on VT 9 and VT 100, which eventually led to ice cream and a Shaw's visit yielding beer and goldfish.

With ominous grey skies looming, we checked out dinner at the Maple Leaf Tavern. It was generally a fine place, with a good beer selection and a slightly pricey menu. But we were really distracted by the fellow who stopped by after a "long day" for two to-go cups of vodka mixed with red wine. I've had some long days myself, but... if you ever see me order vodka mixed with red wine, call a doctor. Please.

nate burger a well earned burger

We headed out from our burger-and-beer dinner with full stomachs and a sense of unease at the somehow even-more-ominous and even-more-grey skies. But our campsite was still miles away, and with bikes and dirt roads, it's hard to say if you'll average 10 miles an hour or 2. So we donned our raincoats and headed out.

rainy bridge high spirits despite the rain

Sure enough, within just a few minutes we were biking down the side of the road in a torrential downpour. But traffic was light, and after a long sweaty uphill day, a shower wasn't the worst thing ever. We eventually made it to forest road 71, a dirt road in absolutely supreme hardpack condition, and rode along the river and past a cool bridge on our way to the campsite at Somerset Airfield. We enjoyed a refreshing Heady Topper as we set up the campsite and turned in for the night.

nate bridge disappointedly too cold and rainy for a swim

Day 2: Somerset Airfield->Winhall Brook Campground

camp day 1 camp #1

It rained on and off throughout the night, so Meg and I slept in a bit Friday morning. By 9 or so, the sun started to poke out between the clouds, so we dried off the tent and enjoyed some Clif bar breakfast. A group of New Yorkers stopped by, and asked if we were done with the campsite -- Meg let them know that we were packing up and would be out in 10 or 15 minutes. So they idled their loud vehicles, drank their Monster, and chain smoked cigarettes right next to our campsite while staring at us as we packed up our panniers. That's probably the fastest I've ever packed up our tent and panniers, but it somehow still felt like a very, very, very long time.

vermont bog vt bog viewz

forest road signs forest road signage that could have been more helpful but was cool to look at nonetheless

double track starting day 2 with some double track

After that awkward experience, we were happy to head over to some technical doubletrack roads that giant RVs couldn't possibly traverse. We enjoyed a morning of relative peace, enjoying the many beaver houses, bogs, lone abandoned bus, and wildflowers with only the mosquitos and horseflies to keep us company. Eventually, the route looped back to forest road 71 and we once again enjoyed the supreme hardpack dirt roads -- a pleasant change of pace from the very rocky doubletrack we were just riding. Sadly, great roads never last, and we were soon greeted by my worst dirt road nightmare: resurfacing. Based on the smell, I can only imagine that the national forest service is dumping loads of bog water on the road to level it out. Based on the riding experience, I can only imagine that the national forest service is actively attempting to make riding a bike or motorcycle as unpleasant as possible by dumping super loose dirt and tons of rocks all over the road. Hopefully the new material will eventually settle down into nice hardpack again, but for now... it was the worst riding experience of our whole trip. Thankfully it was just a few miles, and mostly through very pretty forest. It did make us appreciate all the other roads a lot more through contrast, I guess.

strawberry unfortunately a little before berry season

meg dirt meg riding that quality vt dirt

bus luckily we took the long detour to see this sweet bus

After a quick lunch break from the awful resurfaced road, we quickly made a turn onto Forest Road 341, aka "International Paper Road", an 18.6 mile singletrack route around Stratton Mountain. With our fully loaded panniers on our bicycles, I'm sure we looked a bit silly to the gravel cyclist and guy hiking with his dog... but it was a really fun route. Technically challenging enough to remain interesting, never so brutally uphill to stop us completely, and with a long rewarding downhill stretch at the end that took us nearly all the way to lunch.

meg doubletrack we truly earned the beers we drank

vt swamp even the swamps in vt are pretty beautiful

meg_singletrack downhill singletrack for miles - putting the mtb skills to good use

nate_ damera nate the camera man hard at work

nate river cleanin' off the feetsies

For linner, we stopped in Winhall (or Rawsonville, or Jamaica? Apparently nobody can agree on what this place is called) at the Workhorse Cafe. I had a poke bowl that was both huge and well executed (especially for someplace so far from the ocean!). Meg had a delectable bahn mi sandwich. They had a decent beer selection to boot. Then we headed over via an indirect (but happy cow adjacent) dirt road to the local beer store for some Focal Banger, and Meg grabbed a quick chocolate/vanilla twist at Honeypie because we apparently cannot go a single day without ice cream.

bahn mi a delectable bahn mi

nate poke some tasty poke

cows happy cows

green mountains thanks to all of these darn trees in VT these are some of our only green mountain views

Then, we headed off to our campsite. Our route took us along a dirt road (big surprise) by the river, which eventually ended at somebody's driveway. But our routing told us to continue straight, and sure enough, at the end of the driveway we found a gate to an almost invisible ATV trail right along the side of the river. We followed that for a few miles, and eventually burst out of the woods in the middle of the Winhall Brook Campground, where we surprised a random person by asking where we could register for our campsite. Considering you have to pass the office just to get into the campsite by car, this random person was very confused... but eventually directed us up the (grueling) hill to the office, where we checked in and got a campground map. It was still pretty early, so we enjoyed some beers and waded in the river before we turned in for the night. It was a great campsite except for the fact that we were woken up by 30 minutes of loud, drunken Kelly Clarkson karaoke at midnight.

creek biking along a beautiful creek

nate meg creek happened to be the same creek next to our campground

camp 2 big perk of organized campgrounds is the picnic table

Day 3: Winhall->Londonderry->Grafton->Brattleboro

By day 3, we were in prime bike touring mode. We woke up before 7, ate a light breakfast, sunscreened and bug sprayed up, and were on our bikes by 8. We set off on another riverside ATV trail, and soon found ourselves at my favorite breakfast of the trip -- Corner Market Deli (sadly, their only internet presence is a Facebook page). I enjoyed one of my favorite breakfast burritos ever, Meg had a fantastic sausage-egg-cheese-biscuit sandwich, they made a competent latte and a cold brew... and the staff was super friendly and helpful, asking about our bike ride and letting us know that we could buy singles of any of the four packs of beer in their cooler. The guy at the counter seemed very impressed that we were riding all the way to Brattleboro, indicating that the route was "waving hand motion." I can confirm that there were a lot of hills. There was also some... very Vermont-y eavesdropping to be had as various locals stopped in, ordered their almond milk cold brews, and talked about the yard and personal farm work they wanted to do. 10 out of 10 experience.

breakfast shoutout to the corner market deli

pavement ends always a delight when you expect a busy road and it ends up being dirt

meg bridge one of many, many cute bridges

After our quick stop in Londonderry, we headed down the many miles of "winding gravel road" to Grafton, where we stopped at MKT: Grafton. This place was bougie compared to Londonderry, but damn was the food great. We ate a donut first, then split an ice cold Heady Topper (despite it being 10:30 AM) and a pesto-bacon-turkey-cheddar-romaine wrap. The donut was so good I bought a second one. I still want to go back to buy some of the local cider and reisling they had on display... and I didn't even bother going near the cheese display, because I'm sure I would have bought pounds of cheese that would have weighed my panniers down even more. One of the biggest downsides of bike touring is the weight limitation.

grafton so much time to stop at all of the amazing local vt markets on our mostly downhill day

whoa whoa

lily pond so many lilies

close up lilies close up lilies

After Grafton, we continued down the road to a snacking spot by the river, and eventually came to a crossroads: we could either take a cool dirt road detour up a very large hill, or stay on the (not very busy) main road and check out a farm stand that sells locally made ice cream. I'm sure you've already guessed that we stayed on the main road and had some ice cream. We even saw one of the cows that produces milk for the ice cream. It was fantastic and absolutely worth it.

picnic table public parks in unexpected places are the best

ice cream barn the cows make the ice cream themselves

ice cream break successfully ate ice cream all 3 days

After ice cream, it was literally all downhill. We met another cyclist who asked all about our trip and confidently introduced himself as Wayne Conway (but probably not this Wayne Conway). We swam in the river under a bridge and enjoyed a refreshing beverage. We enjoyed our last taste of dirt roads. And then we got back to the car, where the parking lot was literally completely full of Massachusetts plates, and the river was chock full of Massachusites. And then when we headed back to Meg's parents, the roads and towns were full of Massachusites...

meg nate river a well deserved swim/bath

nate swim bridge confusing everyone else at the swimming hole with our mode of transport

Anyway, it was a great ride. I'm glad we started it on a Thursday.

meg cars and... done!


Our longest bike tour ever was an awesome time. We experienced Vermont in a way I've never experienced it before, carrying our food, water, trash, and camping supplies on our bikes every step of the way. Not showering is not that big a problem when you're always outside, and swim once or twice a day. My dynamo setup provided us with light and power to recharge our phones for navigation, and ridewithgps ensured that we could navigate with or without cell service.

butterfly many butterflies

I could absolutely live off of my bicycle for weeks at a time. So could Meg. Maybe we will sometime. I'm gunning for a grand European bike tour next spring.

If you're interested in our route, check it out at ridewithgps.