Self Guided Walking & Hiking Tours in Vermont

If you like to hike or walk, but don’t want to be confined to a daily group schedule, a self-guided Vermont hiking vacation is ideal.  Benefit from our 43 years of experience in searching out rewarding trails and fine Vermont country inns. These vacations represent the ultimate in adaptability to your specific wishes.  The hikes are as many and as varied as you could imagine.  Hiking Vermont’s Long Trail, a wilderness trail along the ridge line of the Green Mountains, is a popular feature for serious hikers, at least for a day or two of a longer tour.  Nearby scenic trails and quiet country roads offer alternatives for pleasure hikers and those who prefer a walking trip.

The hiking/walking season runs from about the second week of May (though some trails like the Long Trail are closed until Memorial Day to let them dry out from mud season) through about the third week of October.  The only 2018 dates we will not be able to book you at any inn in our network are Friday and Saturday, October 5 & 6.  This is the local college family visit weekend, and the inns are not able to facilitate the hiking program for those two nights.  Other than that, because of the number of inns in our network, we are generally able to book a trip on any date you wish by booking a night at an alternate inn in the case that a particular inn is sold out for a wedding, reunion, or just a busy date.

Below are a few popular combinations, but remember that all trips are custom-made for you; these are simply some of our guests’ favorite itineraries. Trips of a few days to those lasting a full week can be arranged.  Self-guided Vermont hiking and walking packages are all-inclusive and feature:  relaxed Old Wold dinner service nightly, comfortable country inn accommodations (private bath; non-smoking inns), full country breakfast, packed brown-bag hiker’s trail lunch, day use fees when required, our hiking trail notes in advance and detailed local maps distributed by the innkeepers, an innkeeper’s “trail talk” (orientation to local conditions) each morning, daily trailhead shuttle to facilitate one-way hiking (except at Crisanver House and Inn at Baldwin Creek, where all the recommended trails are loops or up-and-downs / out-and-backs), housekeeping and waitstaff gratuities, and Vermont rooms and meals tax.  Your only out-of-pocket expense on tour is alcohol if desired.  Please see our FAQs page for more information including a one-minute video explaining the logistical support provided.

Self Guided Vermont Hiking Itineraries

All package prices are “per person double occupancy” (ppdo).


The Heart of Vermont

One of our most-requested itineraries, this is a wonderful sampler of all things Vermont.  The inns range from four-room hideaway with onsite vineyard, winery, and craft brewery to a Select Registry property nestled in an evergreen glade beside a tumbling stream.  Treasure hunt:  which one of these inns has Robert Frost’s snowshoes hanging over the fireplace?  Hikes on this itinerary include the many options of the Moosalamoo National Recreation Area and other Green Mountain National Forest trails.  Stay at Fox Creek Inn, The Inn at Neshobe RiverChipman Inn, and Mountain View Inn.

2017 package, 4 nights:

$725 per person double occupancy Summer ($1450 per couple); $995 single occupancy (one person / private room)

$825 per person double occupancy Foliage ($1650 per couple); $1125 single occupancy (one person / private room)

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The Hiking Gourmet

Hike your choice of Vermont’s trails near each inn by day, followed by evenings of epicurean delights.  You’ll stay at inns known for their innovative cuisine, at some inns enjoying a full-menu restaurant and at other inns a table d’hote (no menu) dining experience.  Stay at Crisanver House, Fox Creek Inn, Lilac InnBlueberry Hill Inn, and The Inn at Baldwin Creek.

2017 package, 5 nights (rate will be slightly higher if including a Friday or Saturday at these inns):

$1045 per person double occupancy Summer ($2090 per couple); $1525 single occupancy (one person / private room)

$1175 per person double occupancy Foliage ($2350 per couple); $1725 single occupancy (one person / private room)

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The Vermont Fresh Tour

An itinerary which stays  at inns that choose to support local, sustainable, and organic agriculture.  All of the inns in our network partially supply their kitchens from on-site gardens, but these also participate in farm-to-table cooperatives or other community sourced agriculture enterprises (CSAs).  Fine day hiking options whet your appetite for evenings of dining as a “localvore”.  Stay at October Country Inn, The Inn at Neshobe River, Blueberry Hill Inn, and the Inn at Baldwin Creek.

2017 package, 4 nights:

$795 per person double occupancy Summer ($1590 per couple); $1195 single occupancy (one person / private room)

$945 per person double occupancy Foliage ($1890 per couple); $1325 single occupancy (one person / private room)

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The Vermont Appalachian

Hike portions of the two oldest long distance hiking trails in the country, the Long Trail (1910) and Appalachian Trail (1937), which run concurrently in southern Vermont.  Here the gently rounded Green Mountains provide a variety of moderate hiking and spectacular views.  High peaks like Killington are an option for more experienced hikers.  Stay at Crisanver House, Fox Creek Inn, and October Country Inn.  Note:  during foliage season, a two-night stay at one inn is required, so this trip becomes two inns / three nights rather than its summer form of three inns / three nights.

2017 package, 3 nights:

$645 per person double occupancy Summer ($1290 per couple); $875 single occupancy (one person / private room)

$725 per person double occupancy Foliage ($1450 per couple); $1025 single occupancy (one person / private room)

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The To-the-Door and From-the-Door Traverse of the Moosalamoo National Recreation Area

You’ll enjoy the “village mouse / country mouse” flavor of your accommodations on this itinerary, which traverses the length of the 20,000 acre Moosalamoo National Recreation Area in Vermont’s Green Mountain National Forest.  With a delightful inn in Brandon or Ripton village as your starting point, you’ll hike to the door of your second inn one day, and from the door of that inn to your third inn the following day.  A great taste of sustainable tourism.  Please click here for a detailed discussion of this itinerary.

2017 package, 3 nights:

$575 per person double occupancy Summer ($1150 per couple); $795 single occupancy (one person / private room)

$645 per person double occupancy Foliage ($1290 per couple); $925 single occupancy (one person / private room)

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Vermont Wine and Cheese — and Beer!

(Not booking at this time)

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Vermont’s Long Trail

Explore the length of central Vermont with our original hiking program.  Patterned after the hut-to-hut system in Europe, this trip allows point-to-point (not door-to-door) hiking along segments of Vermont’s Long Trail, the nation’s oldest long-distance hiking trail.  An innkeeper-assisted shuttle allows you use of your car.  Based on guest interest, this itinerary has now been modified to include some Appalachian Trail terrain early in the tour.  Evenings will be spent at the following inns: October Country Inn, Fox Creek InnBrandon InnBlueberry Hill Inn, Chipman Inn, and Mountain View Inn.

2017 package, 6 nights:

$1095 per person double occupancy Summer ($2190 per couple); $1625 single occupancy (one person / private room)

$1275 per person double occupancy Foliage ($2550 per couple); $1845 single occupancy (one person / private room)

2017 package, 5 nights:

$945 per person double occupancy Summer ($1890 per couple); $1395 single occupancy (one person / private room)

$1125 per person double occupancy Foliage ($2250 per couple); $1625 single occupancy (one person / private room)

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BACK IN 2017: No-driving-required format

Through our partnership with a veteran local guide and naturalist, we are pleased to offer a self-guided inn to inn trip where you don’t need to do any driving at all.  Our facilitator Bruce will design an itinerary includes all lodging and meals on-trip (on the occasional night when dinner is not available at an inn, a reduction in price is made), provide you with a trip itinerary, maps for each day’s hike, transport your luggage, and shuttle you to/from trailheads and other places (when needed).  Pick-ups / drop-offs at Burlington, VT Airport or nearby train/bus stations are available.  Trip lengths of 2 – 7 days are possible.

2017 sample package, 4 nights, 5 days: $1,400 per person double occupancy ($2,800 per couple) or $1,800 per person single occupancy May-October.

To book this trip or request more information, please send us an email or choose “Custom Trip” from our reservation form and in the comments box, note “2017 No-driving with Bruce”.


All package prices are per person double occupancy (ppdo). A few summer weekend and all fall foliage trips may require two-night stays at some inns; please contact us for availability.