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 44 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 2019 dates we will not be able to book you at any inn in our network are Friday and Saturday, October 11 & 12.  This is the Columbus Day holiday 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.

All trips are custom-made for you. Trips from a couple of 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 Inn at Baldwin Creek and Swift House Inn, 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.  A limited number of rooms with two beds are available if desired (please request at time of booking).

Self Guided Vermont Hiking Inns

Simply tell us your arrival date and number of nights, and we’ll design an itinerary featuring inns in our network in a logistically sensible progression, offering a variety of hiking trails and unique lodging and dining.  Stay at:

October Country Inn, Bridgewater Corners

Mountain Top Inn, Chittenden

Brandon Inn, Brandon

Lilac Inn, Brandon

Inn at Neshobe River, Brandon

Blueberry Hill Inn, Goshen

Chipman Inn, Ripton

Swift House Inn, Middlebury

Inn at Baldwin Creek, Bristol

Mountain View Inn, Fayston

We generally try to incorporate the three-night traverse of the Moosalamoo National Recreation Area (Please click here for a detailed discussion) as the core of any trip, and build out additional nights from there.

All package prices are “per person double occupancy” (ppdo).  SAMPLE PRICING FOR POPULAR TRIP LENGTHS BELOW.  Your trip cost will depend on the specific inns we are able to include, whether dinner is not included one night, etc.

2019 Vermont Classic 6 night trip:  Summer $1245 ppdo / $2490 per couple or $1795 ppso (solo hiker / private room)

2019 Vermont Classic 6 night trip:  Foliage $1425 ppdo / $2850 per couple or $1995 ppso (solo hiker / private room)

2019 Vermont Classic 5 night trip:  Summer $1145 ppdo / $2290 per couple or $1595 ppso (solo hiker / private room)

2019 Vermont Classic 5 night trip:  Foliage $1245 ppdo / $2490 per couple or $1795 ppso (solo hiker / private room)

2019 Vermont Classic 4 night trip:  Summer $875 ppdo / $1750 per couple or $1345 ppso (solo hiker / private room)

2019 Vermont Classic 4 night trip:  Foliage $995 ppdo / $1990 per couple or $1545 ppso (solo hiker / private room)

2019 Vermont Classic 3 night trip:  Summer $695 ppdo / $1390 per couple or $1095 ppso (solo hiker / private room)

2019 Vermont Classic 3 night trip:  Foliage $795 ppdo / $1590 per couple or $1195 ppso (solo hiker / private room)

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AGAIN IN 2019: 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.

2019 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 “2019 No-driving with Bruce”.


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