Trip Fit Checker
Four questions get you the same answer a guide would give you at the trailhead.
Group size, experience, the longest one-way distance you're actually comfortable with, and what you want out of the trip. No account, no quiz with twelve screens — one form, one answer, and a reason for it.
Why four inputs and not fifty
Every guide who's stood at a trailhead and sized up a group asks some version of the same four things before deciding what to do with them: how many people, what have they actually walked before, how far can they honestly go, and what are they here for. We built the checker to ask exactly that and nothing else — no address, no email, no account, just the four questions a foreman asks before the boots hit dirt.
It isn't a quote and it isn't a booking. It's a router. Fill it in, get a page and a reason, then call or send an inquiry if that page is the one you want.
Run it
Check your fit
Set the four fields below. The result updates when you press Check fit, or when you change an answer after you've already run it once.
How the routing actually works
The logic behind the answer
Trail work on your own land routes straight to Trail Building & Maintenance no matter what the other three answers say. That's a contracting question — a measured run of trail and a drainage problem — not a guiding fit question, so group size and hiking experience don't change the outcome.
Wanting to learn navigation routes to Wilderness Navigation Skills, and the checker picks between the two courses on that page based on experience: new to hiking or a few times a year under 3 miles points to the half-day Map & Compass Clinic, and more experience than that points to the two-day Backcountry Navigation Course with its night navigation leg.
A multi-day trip only routes to Custom Multi-Day Expeditions if both other answers back it up — experience above new to hiking, and a comfortable one-way distance above 3 miles. If either one falls short, the checker sends you to Guided Hikes instead and says exactly what didn't clear the bar, because a multi-day traverse runs six-plus miles a day for two days or more, and finding out you can't sustain that on day two of a backcountry trip is the wrong place to find it out.
A guided day out splits three ways inside Guided Hikes: under 3 miles points to the Ridge Walk Half-Day, and 3 to 6 miles with regular off-trail experience points to the Summit Trek Full-Day. In between — say, comfortable to 6 miles but new to hiking — the checker still gives you the Ridge Walk, because the Summit Trek climbs harder than its mileage suggests and the honest first booking is the shorter one.
One rule applies on every branch except trail work: past eight people, the note tells you to call ahead instead of booking straight through. A ninth walker on the Summit Trek changes the start time, because we're not sending one guide out with more people than a single foreman can watch on exposed rock.
Where it can send you
All four service pages exist for the checker to point at. If you'd rather read first and skip the form, here's the same four destinations directly.
Guided Hikes
Half-day, full-day, and headlamp routes for groups who want to be led, not taught.
Navigation Skills
Map, compass, pace count, and dead reckoning, taught on the ground you'll use it on.
Custom Expeditions
Private multi-day traverses and family treks, planned around your dates and pace.
Trail Building
Tread and drainage rebuilds, stone steps, cribbing, blazing, and signage on land you manage.
Still not sure after running it?
Call and describe the group. A five-minute conversation covers ground the checker can't — old knee injuries, a scared-of-heights teenager, a landowner's specific drainage complaint.
- Office
- 71 Chesterfield Rd
Westhampton, MA 01027-9633