Roundabout Brattleboro Bikepacking

Not Made of Sugar Edition

I spend entirely too much time on Bikepacking.com looking at routes and daydreaming about the pleasures of exploring time and space with everything I need loaded to my bicycle. As a subscriber of their print publication as well, there’s a regular feed of tales from the road that fuel my desire to truly experience the details of where we live. Less blazing my own path forward and more leaning in to those who know the best roads and the great places to stop for a meal to see the very best of what the location has to offer.

After tackling (and being humbled by) the Green Mountain Gravel Growler last fall, I decided to scale back and focus on building my skillset on overnights and 3 day adventures. Fortunately Roundabout Brattleboro registered as a great way to experience a mini-GMGG … and my adventure partner was totally game for a shorter route that fits nicely in a 3-day weekend.

In the ten days leading up to the trip however, it became apparent that Mother Nature was not planning to cooperate for the second long holiday weekend in a row. The first being Memorial Day weekend, which Curt and I had planned to ride the Delaware County Catskills Dirt Circuit but canceled due to rain and cold. The forecast called for two of the three days to be a steady rain with the third day a toss-up. Determined to stick to the plan despite the rain, we pivoted from camping to booking lodging in Wilmington and Londonderry. 80% less packed gear was nice!

Growing up, any time it was raining and I didn’t want to go outside, my mom would remind me I’m not made of sugar so I won’t melt if I get wet. So I dubbed this trip the Not Made of Sugar edition.


Day One: Where the Hills ArE

  • Making a conscious decision to ride bikes for at least 48 hours with up to 2″ of rain expected
  • the woman riding a unicycle under an umbrella, looking super unphased by the weather
  • Climbing 3,200′ in the first 24 miles felt much more accessible than it sounds
  • Running into a solo bikepacker on the same loop with full camping gear at lunch in Jacksonville
  • Coffee and warm sandwiches for lunch
  • Spillway at Harriman Reservoir
  • Catamount XC Trail is a GEM that should be savored
  • Hot shower and comfortable bed waiting for us at The Nutmeg Vermont

Day Two: Where the Mud Is

  • 10* cooler temps and expected light rain all day.
  • Replacing our disc brake pads before setting out (due to the wet and dirt from Day One)
  • Deciding to skip Castle Brook Rd since conditions were subpar on even the dirt roads (pretty soupy to peanut buttery)
  • Arriving at USFS 325 and deciding to remain on Forest Road 71 for above reasons (we missed the bus because of this decision)
  • Forest Road 71 is actually very lovely
  • A group of guys at a dispersed campsite with a huge fire going, asking if we wanted to come hang out with them and their red solo cups (and other altering substances)
  • Sitting at the gate for IP Road, weighing an up to 2 hour slog through mud or sticking to the road to make up time and get to resupply (and potential warmth)
  • Low traffic backroads climbing Stratton south to north with our rain jacket hoods down for the first time in the trip
  • Descending into Winhall in a blinding rainshower (funny how weather can be different on opposite sides of a mountain)
  • Seeing our fellow bikepacker at Winhall Market. He confirmed camping was super soggy and the trails were muddy.
  • More coffee and a sandwich on the front porch swing, shivering in the rain
  • Lovely dirt along the Winhall and West rivers
  • Deciding to head into Londonderry to the bike shop to get another pair of brake pads (sadly, they didn’t have the specific brake pad my bike needed – but the rain stopped and the sun came out!)
  • Another hot shower, short walk to a tavern for dinner on the patio, and comfortable bed at the Snowdon Chalet

Day Three: Where Redemption is FounD

  • The weather gods have smiled upon our sacrifice and provided a perfect day for our final leg of the journey – mid-60s, partly cloudy, no rain
  • Coffee and continental breakfast on the motel porch to strategize the day, mist artfully decorating the mountain tops
  • Knowing today’s route trended downhill on long stretches of backroads
  • Most importantly, FRESH BIBSHORTS today!
  • Route 121 at mile 94ish was a little slice of heaven
  • early stop at Grafton Market for pre-lunch. Enjoyed half and decided to go for the final off-road section
  • Ledge Rd is a GEM that also should be savored.
  • We didn’t see our fellow bikepacker but we did see his tracks
  • Brookline/Grassy Brook Rd featured a gentle incline to mile 118, then it’s all downhill to the end
  • Eating the rest of our wraps on the side of the road, bike propped against a split rail fence while we soak in the farmland
  • Finishing on the beautiful Quarry Rd and the West River Trail

Pro Tips

  • Plan ahead – but be flexible and adapt plans to conditions. Research your route, watch the weather, and adjust along the way. Knowing when to deviate from the plan in favor of health, safety, and fun is key. Pivoting from camping in the rain to lodging, making route edits along the way to save energy and time exposed to the elements, meant stripping away a layer of survival that was unnecessary for a three-day trip. Be safe, have fun. Pick two.
  • Bring extra maintenance items, especially on wet and muddy trips. Curt brought a can of WD40 to keep our derailleurs functioning. Checking and replacing our brake pads on Day Two meant we could continue our journey safely.
  • Pack for the weather. Curt’s fashion choice of rubber banded plastic bags over his shoes kept his feet warm and dry on Day One. We also brought extra socks for each day. I definitely wished I’d brought a thermal long sleeve instead of just a regular long sleeve jersey to better retain my core warmth. It was a tough call though – day two was supposed to be in the 60s, not the 50s, when I drove up to Vermont. Certainly had room in my pack for the “extra weight” of a warmer jersey and it wouldn’t have been terrible to have that option.
  • Water Resistant is NOT Water Proof. Know the difference. Packing my items in freezer zip-lock style bags kept everything in my panniers dry despite 2″ of rain and riding through muddy conditions. Side benefit: using quart sizes kept everything modular and organized!
  • Lube your downtown. Wet conditions mean extra chafing opportunities as skin gets waterlogged. Don’t skimp on the chamois cream if you know you’ll be out in the rain all day.
  • Eat, eat, eat. The best nutrition plan for me has been to start eating an energy bar within the first hour of riding and keep eating a bite every few miles. Eat real food as often as possible. Do not underestimate the restorative powers of coffee, pickles, and potato chips.

Fantastic adventure overall! Joe Cruz routes combine scenery with challenging terrain to create an uniquely amazing adventure. Guaranteed to be the best roads and trails available! Do not underestimate these routes though … enjoy the time spent experiencing the textures of the land.

Curt and I are already talking about our next trip and strategizing the GMGG Redux planned for this fall. We even created a day-trip loop to go back and bag the two trails we skipped this time due to conditions.

Hope to see you out there!

Link to Strava of the ride


Packing List

The Bike & The Packs

Salsa Cutthroat GRX600, size 52
modifications: 11-40 cassette
Teravail Sparwood 2.2″ tires
Salsa bolt-on framebag
Revelate Designs Egress Pocket
Revelate Designs Nano Panniers
Revelate Designs Gas Can
Topeak Explore MTB rack
26oz water bottles, mounted to fork

Attire On the Bike
Non-Bike Attire & Accessories
  • Title Nine Swealter Shelter dress
  • softcup bra & underwear
  • shorts and tshirt to sleep in
  • toiletries (travel size toothbrush, toothpaste, deodorant, tweezers)
  • medications sorted into plastic jewelry bags (morning, afternoon, evening)
  • day hike first aid kit
  • wallet pouch with laminated photocopies of my ID, insurance card, and covid-19 vaccination card, cash, and a credit card
Mechanical & Tools
  • multi-tool, tire levers, CO2 for MTB tires
  • spare tubes
  • spare brake pads
  • spare shifter cable
  • chain lube and rag <– rag got soaked and was useless. used paper towels and napkins available at our lodging
On-bike Nutrition
  • ClifBars, assorted
  • Skratch Labs gummies (sour cherry is my fave)
  • Skratch Labs energy bars, assorted
  • Skratch Labs hydration, individual packets

Author: Laura

wife. mother. kick-ass girl. all mountain, all road adventurer by bike.

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