Custom Multi-Day Expeditions
A multi-day trip is planned around your group's pace before it's planned around mileage.
Two formats, both private: a multi-day backcountry traverse for groups who can already walk six-plus miles a day, and a single-day or overnight family trek paced to whoever in the group walks slowest. We plan water, camps, and any permit the route needs before we hold a date, not after.
What this page covers
Custom expeditions are the two trip types that don't fit a fixed schedule: the Multi-Day Traverse and the Private Family Trek. Both are guided by someone who has personally worked the ground you'll be walking, because that's the same person who cut the tread and knows where it washes out after rain.
Everything else we run — the Ridge Walk, the Summit Trek, the navigation courses — sits on a published day. These two don't. A traverse might start on a Tuesday because that's when a four-day weather window opens up in October. A family trek might get built around a grandmother who hasn't carried a pack since 1998 and a nine-year-old who has never carried one at all. Neither fits a template, so neither gets one; we build the route after we talk to you, not before.
We do not run trips outside New England, and we don't stretch the crew's drive time to chase a booking somewhere the region doesn't include. If your trip is on ground we haven't walked, we'll say so on the phone before anything gets scheduled.
Multi-Day Traverse
Price basis: per day, per group
Two or more days, six-plus miles a day, backcountry camps between. This is the trip for a group that's already comfortable off-trail and wants terrain, not a rest stop. Routes link ridge sections and valley crossings across the Pioneer Valley and Berkshire foothills, chosen after we hear how many days you've got and what kind of ground you want under your boots — talus, hemlock duff, exposed rock, or a mix.
We plan camps on flat, drained ground away from the drainage lines we'd otherwise be cutting on a work day, and we carry a filter as backup even after we've marked water sources on the route. If the forecast turns hard — not a little rain, a genuine front — we move the date. We'd rather reschedule a traverse than run one into weather that turns a stream crossing into a decision nobody should have to make eight miles from a road.
| Item | Detail |
|---|---|
| Pace | Six-plus miles a day, two or more days |
| Camps | Backcountry, sited on flat ground clear of drainage lines |
| Group cap | Eight; larger parties split across two guides or two start dates |
| Water | Sourced and filtered along the route, marked out before departure |
| Permits | Any camping or access permit the route crosses is pulled by the crew before a date is held |
| Price basis | Per day, per group |
Private Family Trek
Price basis: flat rate per group
Single-day or overnight, paced for mixed-age groups. There's no mileage target on this one. We ask who's coming — ages, any knee that's given someone trouble, whether anyone's carried a pack overnight before — and we build the route around the slowest walker rather than making the slowest walker keep up. A trek with a seven-year-old and a seventy-year-old on it looks nothing like a trek with three fit adults, and it shouldn't.
The overnight version stays close to a car-accessible or short-carry camp; we're not putting a first-time nine-year-old two ridges deep with no way out but a full day's walk. If a family wants the harder version later, that's a different trip, and by then everyone knows what they're asking for.
| Item | Detail |
|---|---|
| Format | Single day out-and-back, or one overnight |
| Pace | Set by the slowest walker in the group, decided after we talk to you |
| Group cap | Twelve, mixed ages |
| Camp, if overnight | Car-accessible or short carry, chosen for easy exit |
| Price basis | Flat rate per group |
Overnight logistics
What we plan before we plan the route
An overnight trip has three moving parts that a day trip doesn't, and we settle all three on the phone before a date goes on the calendar.
Permits
Some of the ground we cross needs a camping or access permit and some doesn't; it depends on who holds the parcel. We check the route against the land status before we quote a date, and if a permit's needed, we pull it ourselves rather than hand you a form. That step alone can push a start date back a week or two on some tracts, so we build in the time up front instead of finding out three days before you're supposed to leave.
Water sources
Every traverse route gets its water points marked before departure — streams and springs we know run through the season, not ones we're hoping are still flowing. We carry a filter regardless, because a source that looked good on the last pass through can be dry, silted, or fouled by the time we're back. Nobody on the trip drinks unfiltered water, guide included.
Group caps
Eight is the cap on an overnight traverse; twelve on a family trek, because the family trek doesn't put people on exposed ridge sections the way a traverse does. Past the cap we don't just add bodies to one line behind one guide — we run two guides, or we split into two start dates. A guide who's watching twelve people on wet talus is watching too many people, and that's the kind of shortcut that shows up as an incident report, not a trip photo.
Where we'll say no
A multi-day itinerary is the booking we'll turn down fastest if the numbers don't add up. If a group tells us they hike a few times a year and their longest day is four miles, we're not putting them on a six-mile-a-day traverse with a pack and two nights out — not because we're precious about it, but because that's how someone ends up hurt eight miles from a trailhead with no cell signal and a slow walk out. We'll route that group to a full-day trek instead, or to the family trek format, and we'll say exactly why on the phone.
The same goes the other direction: if a family trek request turns out to be five strong adults who all backpack already, we'll tell you the traverse is the better trip and probably cheaper for what you actually want out of it. We'd rather lose a booking to an honest redirect than run a trip that isn't the right shape for who's walking.
If this isn't quite the fit
Not everyone asking about a multi-day trip is ready for one yet, and that's fine — most people who end up on a traverse started on a full-day Summit Trek first, just to see how their legs and their gear held up under real mileage. If the goal is learning to read the ground yourself rather than being led across it, the navigation courses cover map, compass, and pace-count work on the same terrain. And if what you actually need is trail work done on land you own or manage — not a guided trip at all — that's a different service: see Trail Building & Maintenance.
If you'd rather answer four questions than read the whole page, the Trip Fit Checker runs the same triage a guide would run at a trailhead and tells you which of these pages to actually book.
Tell us the dates and the group, and we'll tell you what's realistic.
Expedition inquiries get a phone call back, not an auto-reply. We'll ask about experience, dates, and how many people before we talk terrain.
- Phone
- +1 (898) 555-4791
- Office
- 71 Chesterfield Rd
Westhampton, MA 01027-9633