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Roundabout Brattleboro — a charming challenge in the New England countryside


Roundabout Brattleboro — a charming challenge in the New England countryside

Bike Touring Collection by mhzhao



13:52 h

138 mi

10,575 ft

Roundabout Brattleboro is an easily accessible two to three-day gravel tour of Southeastern Vermont that is as charming as it is challenging. On the one hand, country roads lead you through sweeping pastoral scenery on your way to wild forest trails between idyllic village centers where general stores staffed by kind locals are eager to cook you a delicious meal or sell you all manner of locally sourced snacks and beverages. On the other, those roads are among the steepest you’ll ever encounter and the rockiness of the mountainous trails is surpassed only by the muddiness of the forested paths. Those factors taken together mean you might not make it to the next village in time for last call. But that’s all a part of the route’s charm.

You might see Bikepacking.com’s 5/10 difficulty rating and assume that this is a beginner-friendly route that anyone could easily pick up and ride, but that rating is softened largely by the route’s proximity to civilization and ample resupply opportunities. One look at the elevation profile should dispel you of that notion — and that doesn’t even account for the surprising roughness of the terrain in many sections.

The ride conveniently starts at a vast park and ride near the interstate with a short descent into Brattleboro’s center, but quickly changes its tune. Before long, you’ll hit the first of many epic gravel ascents to come on the first day. In the first 25 miles, the grade figure on my GPS would often exceed 12% for minutes at a time. By the end of that section, the elevation gained figure was already well above 3,000 feet. This ratio of mileage to elevation would be difficult enough on a road bike, but doing it on a loaded dirt-touring rig is a much more gruelling affair.

The lion’s share of the climbing happens in the first third of the route, but the challenges are far from over. As indicated in my Highlights, the terrain can be quite challenging for extended periods of time — especially during or right after it rains. Expect lots of mud and puddles on any off-road surface and descend with caution to avoid sharp, sidewall-eating rocks hiding beneath the tall, dew-laden grass hanging over every trail. Although there are no stream crossings that require carrying your bike, a number of the trails and logging roads appear to double as seasonal watersheds depending on the timing of your attempt.

With all that in mind, I can’t recommend attempting this route with anything narrower a 47mm tire, unless you don’t mind hiking your bike for extended periods of time. 95% of the route is rideable on a 700c x 35c gravel/CX bike, but 5% of the 137-mile route is still nearly 7 miles, which is a sizeable day-hike. The ideal bike for this route is somewhere between a rigid mountain bike and a dirt touring bike. My Crust Evasion Lite fitted with 650b x 2.25” Schwalbe Thunder Burts was perfectly suited to the terrain I encountered, despite being a bit slower on the paved portions.

As for equipment, plan for rain and wear shoes that can dry quickly (such as 2-cleat MTB shoes), or that you’re comfortable getting wet (like sandals with flat pedals). I’d recommend leaving the cook kit at home, as there’s plenty of delicious food to be bought along the way that’s going to be much more satisfying than any rehydrated meal. The Jacksonville and Grafton general stores were both lovely and I also enjoyed my hot lunch at the Workhorse Cafe.

If you’re doing this route alone, as I did, I recommend a two day attempt with camping somewhere near the halfway point off of National Forest Road 71. If you’re doing it with a group, stretching to three days allows for more swimming opportunities and beer breaks. Plan to camp somewhere near the reservoir on the first night and try to book a group site at Winhall Brook for the second evening.

On The Map


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Roundabout Brattleboro

137 mi

10,125 ft

10,125 ft

Last updated: April 26, 2022

Tours & Highlights

  • Day 1: Roundabout Brattleboro

    60.9 mi
    9.2 mph
    6,100 ft
    4,150 ft

    A friend of mine who attempted this tour as a three-day trip about a month after I did referred to day one “the hardest day” they’d ever had on a bike due to all the climbing.


    6,100 feet in 61 miles is not so bad, but some 4,000 of those feet climbed come in the first 27 miles or so. It’s hard enough

    by mhzhao

  • 07:16
    76.7 mi
    10.6 mph
    4,475 ft
    6,350 ft

    Day 2 started at dawn with a speedy descent down a wide, gravel road through the golden morning mist of the Green Mountains. This was in preparation for the reward to come: IP road.


    My friends who’d tackled the tour a couple months prior mentioned this section as the highlight of their trip and it didn

    by mhzhao

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Collection Stats

  • Tours
  • Distance
    138 mi
  • Duration
    13:52 h
  • Elevation
    10,575 ft

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