Since 2009
Sixteen years in, the founder still leads the Saturday crew and the harder trips himself.
This page covers where the outfit came from, who is on the crew today, and exactly how the segment logbook decides who guides a given hike.
How it started
Eleven seasons of volunteer crew work, then a truck of his own
Jasper Cole spent eleven seasons on Massachusetts Trails Association volunteer trail crews before he went independent in 2009. Volunteer crews teach you fast what a paid one can't: what a tread does after three winters with no maintenance budget behind it, and how much of trail failure traces back to drainage nobody rebuilt when the erosion was still minor.
He started with a used pickup and a set of hand tools he'd bought himself over those eleven seasons — rock bars, mattocks, a come-along that had already earned its scars. No investors, no franchise plan. Just a truck, a trailer, and a waiting list of land trusts and hunting-and-fishing clubs who needed tread rebuilt on ground the volunteer crews couldn't get to on a fixed schedule.
Sixteen years on, the truck and trailer are newer but the model hasn't changed. Seven people, one crew, no subcontracted labor. Cole still swings a mattock on the Saturday crew most weeks, and he still personally guides the multi-day trips that carry the most consequence if the lead guesses wrong about the terrain.
A mattock, a rock bar, and a come-along move more earth than a rented mini excavator that can't get past the gate.Jasper Cole
That line isn't a boast about hand tools for their own sake. Most of the ground this crew works — conservation land, private hunting-and-fishing tracts, backcountry approaches — has no vehicle access wide enough for machinery. The come-along and the rock bar aren't a stylistic choice. They're what actually fits through the gate.
1600 hours a year, give or take
Sixteen years on the timeline
- 2009 Jasper Cole leaves Massachusetts Trails Association volunteer crews and starts the outfit with one truck and a set of hand tools he already owned.
- 2012 First multi-year maintenance contract with a Pioneer Valley land trust brings on the second and third full-time crew members.
- 2016 Crew reaches seven, the size it has held since. The trailer replaces a second truck once the tool load outgrows what one bed can carry.
- 2019 Guided hikes formalize into a scheduled offering rather than informal walks for maintenance clients who asked to come along on a workday.
- 2021 The two-year drainage guarantee is written into every rebuild contract after a wet spring tests three prior seasons of work at once, and it holds.
- 2025 Sixteenth year trading. Same seven people, same one truck and trailer, same refusal to take work outside the Pioneer Valley and Berkshire foothills.
The crew
Seven people, one truck, one trailer
The crew has held at seven for close to a decade. That's a deliberate ceiling, not a hiring shortfall: seven is what one foreman can watch on a single job site without losing track of who's swinging what near whom. Rock bars and mattocks are not tools you want being handled by someone nobody is watching.
Every member of the crew does both jobs. There's no separate guiding staff and no separate construction staff. Whoever is leading Tuesday's map and compass clinic may have been setting cribbing on Monday, and the schedule is built around that overlap on purpose rather than around it.
No subcontracted labor, on either side of the business. If the crew can't cover a job in a given week, the job waits for the crew rather than going out to a rented labor pool that has never seen the ground.
How trip leads get assigned
The segment logbook, explained in full
This is the one system on the site that decides who guides your trip, and no other page walks through how it works.
Every trail the crew maintains is broken into segments, each with a short code — a ridge crossing, a switchback set, a stream ford. For each segment the logbook records who built or last serviced it, what work was done, and when. Drainage checks, blaze repainting, cribbing repairs: all of it goes in against the segment, not against a generic trail name.
Blue paint blazes fade in about four years under hemlock canopy, faster in open sun and slower in deep shade, so the logbook tracks each segment's repaint cycle individually rather than assuming one schedule fits the whole trail system. We repaint on a three-year cycle rather than wait for someone to lose the trail at dusk.
When a guided trip is booked, the segment codes for that route get checked against the logbook before a guide is assigned. If the person scheduled to lead hasn't personally serviced that segment within a reasonable window, the assignment changes. That's the rule, and it overrides convenience: a guide's calendar availability does not outrank whether they actually know the current state of that ground.
The same record backs the two-year drainage guarantee on the construction side. If a client calls about water pooling on a rebuilt section, the logbook tells us in minutes which crew member set that drainage and when, so the right person goes back out rather than whoever happens to be free.
What we won't do
Two refusals we hold to on purpose
We don't do landscaping and we don't build backyard paths. That's not a snobbery thing — the tools, the grading standards, and the erosion math for a residential path are different enough from backcountry tread that doing both well would mean doing one of them worse. We stick to trail.
We don't lead trips outside New England. Every guide on this crew has personally walked and serviced the ground they lead clients across. That's the whole premise. Guiding somewhere none of us has worked would just be a stranger with a map, and clients can hire that anywhere.
Want to know who'd lead your specific trip?
Tell us the trail or the land in your inquiry and we'll check the logbook before we quote a guide, not after.
- Office
- 71 CHESTERFIELD RD
WESTHAMPTON, MA 01027-9633
United States - Phone
- +1 (898) 555-4791