Vermont Walking & Hiking Tours | Great Freedom Adventures
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The Colors of Vermont Hiking & Walking Tour

The Colors of Vermont Hiking & Walking Tour

per person

4 days/3 nights

vermont-hiking-walking-tour-2Walk Amidst the Colors of Vermont

Vermont: for most of us, just hearing the name conjures up postcard images of white farmhouses featuring red barns, black and white cows grazing peacefully in green fields, red covered bridges spanning sparkling blue rivers and multicolored hillsides bedecked in shades of red, orange and yellow. On The Colors of Vermont Walking Tour, step into scenes as beautiful, or more so, than those in your mind’s eye. With decades of experience hiking the trails in the region, Great Freedom Adventures has selected treasured walks that bring guests right into quintessential scenes that reveal the colorful beauty – and the true heart – of Vermont life.

Acclaimed Woodstock Vermont

Discover lovely Woodstock, a picture perfect Vermont town that provides easy access to a trove of breathtaking walks. Explore the hills and valleys of Woodstock and the surrounding towns, with time built in to explore the charming streets, covered bridge, country store, upscale shops and fine art galleries of the village itself.

vermont-walking-tour-11From Fern Groves to Hilltops
With your guide, learn about native plants and animals while walking along woods trails and carriage roads under a multicolored leaf canopy. Watch for deer, wild turkeys, fox and much more. On some days, a gradual climb leads to long-range viewpoints – ones that display familiar scenes featured on Vermont postcards and in travel magazines. Wide panoramas viewed from up high reveal landscapes of peaceful farmland, meandering rivers, Green Mountain ridgelines, church steeples and village homes nestled among the trees.

The Changing Colors of Vermont
Choose from spring, summer or fall departures: each season offers its own unique delights. Spring brings a bright green landscape bursting with new life and the smell of fresh earth, summer reveals deepening colors, warm sunshine and the delicious smell of cut hay, while fall serves up radiant colors and the crunch of fallen leaves underfoot. Whenever you choose to travel, there is no better way to experience these awe-inspiring scenes than by walking and hiking right through them with local experts Great Freedom Adventures.

Note: This walking tour runs concurrently with the four-day Vermont biking tours making it an ideal choice for couples, friends or family traveling together who have different interests. One or more people in the group may do the biking tour while others may select the walking tour. Both tour groups will stay in the same lodging and eat together. Some portions of the tour days may overlap as well.

Tour Highlights:

  • Discover the remarkable beauty of Vermont while walking scenic trails and carriage roads
  • Stay in a fine country inn in Woodstock, VT
  • Enjoy meals prepared by the region’s best chefs
  • Visit a sugarhouse and learn how maple syrup is made
  • Learn about plants and animals native to Vermont
  • Visit Quechee Gorge – Vermont’s deepest gorge
  • See master glassblowers create fine glassware at Simon Pearce Glassblowing
  • View covered bridges and waterfalls
  • Visit Woodstock’s Marsh-Billings-Rockefeller National Historical Park and learn about the founders of America’s conservation movement
  • Tour the Rockefeller mansion
  • Explore the shops and sights of Woodstock
  • Enjoy dedicated service as you discover the beauty and the colors of Vermont

Day 1

vermont-walking-tour-4Begin your Vermont discovery just outside of Woodstock by walking on a class 4 road with scenery that is, simply put, stunning. This ancient road is perfect for walking because cars are scarce but wildlife abounds. The route begins with nearly level terrain that passes beneath a multihued canopy of towering maple, birch and beech trees. Dappled sunlight hits the forest floor highlighting wildflowers, ferns and mosses and making streams and ponds sparkle. While walking through this peaceful place, listen for the soft gurgle of the streams, the rustle of the leaves and the songs of the birds. Emerge from the trees onto a wide open panorama of fields, stonewalls and farmhouses, all set off by views of distant mountain ridges as far as the eye can see - a sight that stops you in your tracks. Continue down the hill passing farms that seem impossibly picturesque. Enjoy dinner at a top Woodstock restaurant.

Walking Distance: 2.6 mi (4 km), Elevation: +23’/-840’ (+7 m/-256 m), easy

Day 2

vermont-walking-tour5Visit a classic Vermont sugarhouse and learn how the sap from maple taps or lines transforms into that most wonderful of tastes: pure Vermont maple syrup.  You may wish to bring some of this liquid gold home with you. From the sugarhouse, travel to Quechee, home to “Vermont’s Little Grand Canyon,” the Quechee Gorge. Walk a trail through the mile long chasm and climb to an overlook 168 feet above the Ottaquechee River. Continue walking along the river to discover a popular swimming hole where intrepid swimmers ride the rapids, while more relaxed folks float in the calm pools. The walk continues on trails cushioned and scented by pine needles, through quiet forests and alongside wildlife-filled bogs and ponds. Enjoy Vermont foods at a picnic lunch under the pines. Next, travel to Simon Pearce Glassblowing and watch master glassblowers create works of art sold in fine shops worldwide. Upstairs, peruse the gift shop, which offers a sparkling collection of hand-blown glassware and Vermont made wood products. Outside, walk along the river to view Quechee’s covered bridge and waterfalls, then see two more covered bridges on the return to Woodstock. Enjoy dinner on your own with excellent options just a walk away. Walking Distance: 3.6 mi (5.9 km), Elevation: +243’/-213’ (+74 m/-65 m), easy

Day 3

vermont-hiking-and-walking-tour-15Walk to Woodstock’s Marsh-Billings-Rockefeller National Historical Park, Vermont’s only national park - one dedicated to the tradition of land conservation and stewardship. Stroll the gardens and grounds surrounding the Queen Ann style mansion and tour the interior of the mansion, a National Historic Landmark.  View the impressive collection of art amassed by Marsh and Billings, including a substantial collection of Hudson River School Art. Next, walk scenic carriage roads constructed in the 19th century by Frederick and Julia Billings in the upland portions of their estate.  Stop at a tranquil 14-acre pond, then continue up to the 1,357’ summit. Revel in the bird’s eye vistas of the town of Woodstock and the Ottaquechee River Valley, views that have graced numerous postcards. Walk down wooded trails back to Woodstock and cross the covered bridge to the picturesque streets of the village.  Enjoy lunch in town followed by an afternoon free to explore as you wish. Visit the fine boutiques and galleries of town, head to Billings Farm to tour the farm and museum, visit the Dana House Museum at the Woodstock History Center, walk more of the area trails, or simply relax at the inn. Enjoy dinner at an excellent Woodstock restaurant featuring delicious creations by a highly talented chef. Walking Distance:  4.2 or 5.0mi (6.7 or 8 km), Elevation: +664’/-667’ (+202 m/-203 m), easy to moderate

Day 4

vermont-walking-tour-16Walk past the town green to a trailhead leading to the summit of a 1,076’ hill. It’s a short and mostly gradual climb with an outsized reward at the top. Enjoy panoramic views north and west of fields, farms and mountain ridges all the way to Killington Mountain, which at 4,235’, is Vermont’s second highest peak. Hike back to the inn and enjoy the last tastes of Vermont at a farewell gathering.

Walking Distance: 2.6 mi (4 km), Elevation: +366’/-368’ (+112 m/-112 m), easy to moderate

woodstock-inn-2Woodstock Inn & Resort, Woodstock, VT - 3 Nights (October Departures)The Woodstock Inn epitomizes New England country elegance. A Conde Nast Traveler Gold Club member, the stately inn and beautiful grounds are ideally located adjacent to the town green, in the heart of Woodstock village. Beautiful sitting spaces and fine dining rooms are enhanced by excellent service. Luxurious rooms feature furnishings handmade by talented local artisans. Additional resort amenities include a tavern, game room, pool, spa, gift shop and afternoon tea & cookies. In addition, GFA guests may use the Athletic Club (indoor pool, hot tub, sauna, steam room, racquet sports, etc.) and participate in classes.

506-on-the-river-inn506 On the River Inn, Woodstock, VT - 3 Nights (May - August Departures)This fine inn set on the banks of the Ottaquechee River was recommended by Conde Nast Traveler as "The place to vIsit." Balconied rooms overlook the expansive lawn and the river. Inn amenities include a restaurant, bistro, country kitchen, library, game room, gift shop, and an indoor pool with sauna.

2018 tours booked by December 31, 2017 will receive the 2017 price (shown)

2017/2018 Dates

October 9-12 | May 25-28 | July 1-4 | July 23-26 | August 6-9 | October 1-4 | October 8-11

2017 Prices

May - August: $1,495, October: $1,895. Per person, based on double occupancy. Single Supplement: $550 ($650 October Departures)

Trip Length:

4 days, 3 nights


Woodstock, VT

Daily Mileage:


Walking Level:

Easy. Easy to moderate on portions of two days.


Dirt roads, carriage roads and woods trails.

What’s Included:
  • 3 nights accommodations in a fine Woodstock inn
  • 4 days of beautiful walks
  • 3 breakfasts
  • 2 dinners
  • 2 lunches
  • Visit to a sugarhouse
  • Quechee Gorge
  • Simon Pearce Glassblowing
  • Admission to Marsh-Billings-Rockefeller National Historical Park
  • Tour of the Rockefeller mansion and gardens
  • Walking guide
  • Daily drinks and snacks
  • Tax and gratuities at inn and restaurants
  • Waterbottle
  • Dedicated service throughout your worry-free tour
Note: This walking tour runs concurrently with the four-day Vermont biking tours making it an ideal choice for couples, friends or family traveling together who have different interests. One or more people in the group may do the biking tour while others may select the walking tour. Both tour groups will stay in the same lodging and eat together. Some portions of the tour days may overlap as well. Frequent Adventurers, GFA alumni, may deduct 5% from the tour price. Please contact us for youth and group rates. Custom dates and duration are available for groups of six or more.

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