The Possibilities

Chase peak color down roads the tour buses can't reach

Southern Vermont turns for roughly three weeks, and the difference between a nice photo and a stunning one is knowing which hillside catches first light on which morning. We track color reports daily and build your route the night before, moving between ridgelines, ponds and back roads as the light shifts. The Jeep handles the dirt roads that lead to the frames nobody else is shooting.

4 hours (sunrise or golden hour)

1–4 guests per Jeep

Mid-September through late October

Learn your camera where the light is actually worth shooting

A hands-on field session for anyone who owns a good camera and has never left it out of auto. We cover exposure, composition, depth of field and reading light, then put all of it to work across three very different Vermont locations. You leave with your own edited-in-camera keepers and a written cheat sheet built around your specific body and lens.

3 hours

1–4 students

April through November

Your best friend deserves a better backdrop than the living room rug

A relaxed loop around the Manchester region built entirely around photographing your dog — or cat, or notably photogenic goat — in settings worth framing. We pick locations with safe footing, low traffic and gorgeous light, and we move at whatever pace keeps your animal happy. Every tour includes a set of edited digital images delivered within a week.

2.5 hours

1–4 guests and up to 2 pets

Year-round

Dashing through the Green Mountains with the top off and the heat cranked

Our Jeeps come out of the garage in December wrapped in garland, bells and a startling number of lights, and we run an evening circuit of the best-decorated homes, farms and village greens in Southern Vermont. Heated seats, wool blankets and thermoses of hot cocoa make an open-air December night in Vermont not just survivable but genuinely wonderful.

2 hours (evening departures)

Up to 4 guests per Jeep

Thanksgiving weekend through the first week of January

Pumpkins, berries, maple and your own Christmas tree, cut fresh

A working tour of Southern Vermont agriculture that changes completely with the calendar: strawberries and blueberries in summer, apples and pumpkins in autumn, and pick-your-own Christmas trees once the snow arrives. We visit two or three family farms, you pick whatever is in season, and the Jeep hauls it all home — tree included.

3 hours

Up to 4 guests per Jeep

June through December, varies by crop

Jeeps in costume. Back roads in the dark. Stories that hold up.

Southern Vermont has more than its share of genuinely unsettling history, and in October we go looking for it after dark. The Jeeps run in full costume, the route strings together old burying grounds, a documented haunted inn and a few stretches of road that locals still avoid at night, and every stop comes with a story we can actually source.

2 hours (after dark)

Up to 4 guests per Jeep

Late September through Halloween

Revolution, robber barons and marble sidewalks

Two towns, two very different American stories, one afternoon. Bennington gives you the Revolutionary War, the oldest surviving Vermont meeting house and a 306-foot monument you can see from three states. Manchester gives you the Gilded Age — marble sidewalks, Hildene, and the era when Lincoln money built a resort town in the mountains.

3.5 hours

Up to 4 guests per Jeep

Year-round

Four centuries of Vermont craftsmanship in a single afternoon

Vermont has around a hundred surviving covered bridges and Bennington County holds some of the finest, including three within a few miles of West Arlington. We visit four or five of them, explain why they were covered in the first place, and pair them with the Greek Revival farmhouses, round barns and white-steepled churches that make up the rest of the built landscape.

3 hours

Up to 4 guests per Jeep

Year-round

The highest peak in the Taconics, by the longest privately owned road in America

Our namesake mountain, and still the best two hours in Southern Vermont. The Skyline Drive climbs 3,248 feet through five distinct forest zones to a summit with views across the Green Mountains, the Adirondacks, the Berkshires and on clear days into New Hampshire. We add three more overlooks on the way back down that almost nobody stops for.

3 hours

Up to 4 guests per Jeep

May through October, weather permitting

Unscripted, unpolished and guided by someone who actually lives here

No fixed itinerary, no script, no gift shop. Four hours on dirt roads with a guide who grew up here, stopping at whatever is worth stopping for: the sugarhouse mid-boil, the cheesemaker who sells out of a cooler on the porch, the swimming hole nobody posts about. This is the tour we would give a friend visiting for the first time.

4 hours

Up to 4 guests per Jeep

Year-round

Vermont's best taprooms, and nobody has to argue about who drives

Four hours, four to five of the best breweries, distilleries and pubs in Southern Vermont, and a professional designated driver for every Jeep in your party. Built for bachelor and bachelorette weekends, milestone birthdays and reunion groups who want the fun without the logistics or the liability.

4 hours

Up to 4 guests per Jeep, fleet available for larger parties

Year-round, Thursday through Sunday

Candles are fine. A mountain summit is better.

A birthday built around a Jeep rather than a dining room table. We decorate the vehicle, plan a route around whatever the birthday person actually likes, and set up a surprise at the destination — a cake at a summit overlook, a picnic by the river, or a full catered spread in a meadow. Works just as well for a nine-year-old as it does for a seventieth.

2–4 hours

Up to 4 guests per Jeep, fleet available

Year-round

One overlook, one photographer hidden in the trees, one yes

The whole proposal, handled. We scout and secure a private overlook, position a professional photographer out of sight, set up whatever you want waiting — champagne, a catered table from a renowned local restaurant, candles and lanterns — and drive you there under an entirely plausible pretext. You only have to remember the words.

2–3 hours

2 guests, plus concealed photographer

Year-round

Arrive like the night actually matters

A cleaned-up, polished Jeep fleet with professional drivers for prom night — far more memorable than a limousine and considerably more fun to photograph. We handle pickup at every house, a scenic photo stop with a mountain backdrop before the dance, drop-off at the venue, and the ride home whenever the night ends.

4 hours, extended packages available

Up to 4 students per Jeep, fleet available

April through June

Guest shuttles, photo runs and a getaway they'll still talk about

Vermont weddings happen at the end of dirt roads, and dirt roads are what we do. We run guest shuttles between lodging and venue, take the couple out for portraits at overlooks the photographer could not otherwise reach, and provide a decorated getaway Jeep for the exit. Full-day and weekend packages available.

Half day, full day or full weekend

Custom fleet, sized to your guest count

Year-round

A field trip that ends somewhere above the treeline

Curriculum-linked outdoor excursions for schools, scout troops and youth programs across Southern Vermont. We build the day around what your class is actually studying — Revolutionary War history, forest ecology, geology, watershed science — and deliver it standing in the place where it happened rather than reading about it.

2–4 hours

Custom fleet, 4 students plus chaperone per Jeep

September through June

Low range, line choice and recovery, taught on real terrain

A proper four-hour off-road driving course on genuine Vermont terrain — rock, mud, water crossings, steep ascents and off-camber descents. Learn low range, tire pressure, line selection, throttle control and self-recovery. Drive our Jeep or bring your own and learn what it can really do.

4 hours

1–3 students

April through November

Hike one-way. We'll be at the other end.

A point-to-point shuttle for hikers, backpackers and thru-hikers across the Southern Vermont trail network — the Long Trail, the Appalachian Trail and the regional day-hike system. Drop at one trailhead, get collected at another, and stop planning your day around getting back to your car.

Varies by route

Up to 4 hikers with full packs

Year-round, weather dependent

Professional routing, cutting and maintenance for private land

Consulting and hands-on trail work for landowners, land trusts and municipalities across Southern Vermont. We route, cut, grade and maintain sustainable trails for hiking, riding, skiing or vehicle access, built to drain properly and survive mud season rather than wash out in the first spring thaw.

Project-based

Landowners, trusts and municipalities

Year-round, construction April through November

Pre-arranged, plowed-road-ready, and your gear rides inside

Pre-arranged private transfers to Stratton, Bromley, Magic Mountain and the regional airports, in vehicles built for the weather that actually closes the roads. Skis, snowboards, bikes and luggage travel inside the vehicle rather than strapped to a roof, and we run when the storm is still coming down.

Varies by destination

Up to 4 passengers with gear

Year-round, subject to availability

Picture vehicles, camera cars and location access

Our fleet, our drivers and our location knowledge, available to film, television, commercial and stills productions working in Southern Vermont. Jeeps serve as picture vehicles, camera platforms and crew transport to locations no production van will reach, with drivers who understand call sheets and hitting a mark.

Day rate or weekly

Scaled to your production

Year-round

Invite-only runs for alumni and local owners

An invitation-only group for past Equinox Expeditions guests and Southern Vermont Jeep owners. Members get monthly group runs on routes we do not publish, trail clean-up days, winter recovery clinics, and first access to new experiences before they go on the site. There is no membership fee — you earn your way in by coming on a tour or owning a rig and showing up.

Varies by event

Members and their guests

Year-round, monthly events