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Hiking boots, skis or snowshoes.

Authentic Vermont, at your own pace.

Vermont hiking mountain challenge


Our most adventurous tour yet. Limited summer/fall availability.

5 days. 75 miles. 10 summits. 20,000' total ascent. Bragging rights and T-shirt included.

Big mileage + big elevation gains = bigger rewards. Starting in East Middlebury and ending with two nights in Stowe, Vermont, this self-guided hiking tour is not for the faint of heart. Approximate daily distance ranges from 7 to 18 miles, including several stretches on the famously challenging Long Trail. Summits include Mt. Abraham, Camel's Hump and Mt. Mansfield (the highest point in Vermont). You'll spend 6 nights at some of Vermont's finest inns so that you can wake up feeling refreshed and ready to explore Vermont's peaks, villages and back roads.


This tour has a total of 3 short shuttles: one to your initial trailhead, one around the midway point, and one on the last day. Other than that, you'll be traveling door-to-door on your own two feet. Hiking experience and basic navigational skills required.

What's included:​​

  • All lodging in small, locally-owned Vermont inns (private bath)

  • All luggage transfers

  • Daily breakfast

  • Daily "trail lunch" featuring local Vermont foods

  • Digital route maps that use your phone's built-in GPS

  • Written directions and waterproof paper map

  • Local shuttles as needed (e.g. if there are no restaurants open for dinner within walking distance of the inn)

  • Green Mountain Challenge finisher's T-shirt

Not included:

  • Dinners

  • Airport pickup/drop-off (available for an additional fee)

Rates (prices include all taxes and fees)

  • Summer (June 1 to September 14), per person double occupancy (PPDO) total: $1,275

  • Fall Foliage (September 15 to October 21), PPDO total: $1,545

  • Single supplement (additional total): $875 Summer, $975 Fall Foliage

6 nights (arrive Sunday, depart Saturday).

Please contact us for details.

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