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Each season in Vermont brings a plethora of adventures and colors to the landscape — pristine white fields and snow-capped pine trees in winter, the pastels of wildflowers and lilacs in spring, deep greens of lush forests in summer, and of course the blazing foliage of yellow, red, and orange during autumn. We enjoy each season for different reasons but love nothing more than to share the summer and fall with our friends, families, and guests. No matter which season you choose, this trip takes in some of the best walks and hikes in northern and central Vermont.
Two quintessential aspects of New England life are experienced on this exploration of Vermont — small towns and pastoral landscapes. We take advantage of all that is available, from great hikes to farm tours. In the evenings, we retire to genteel country accommodations in charming locations.
Arrival; Transfer to Woodstock
This morning, upon meeting our guides in the lakeside city of Burlington, we make our introductions before driving south to the charming village of Woodstock. Woodstock is a walker's paradise, where you can literally step outside your door onto an interconnected, compact system of pathways, trails, and carriage roads. They lead from the historic center of town, across meadows and woodlands, through a national park, and up to scenic vistas overlooking valleys, villages, and rural countryside.
Following lunch and a brief orientation on the week's adventures, we may choose to set out on a hike or a short stroll. We plan to explore the historic carriage roads and paths of the Marsh-Billings-Rockefeller National Historical Park, a living symbol of three generations of conservationist thought and practice. We learn about land stewardship and conservation as well as the histories of three American families by visiting the mansion and gardens where these exceptional people lived and observed nature.
We'll return to the village center of Woodstock where you are free to set out on your own to explore this quintessential New England town. Chartered in 1761, Woodstock is a typical, quaint Vermont village with historical brick homes, a covered bridge, a village green, and a small "downtown USA" main street.
For the next two nights, we will be staying at the area's finest accommodations - the Woodstock Inn and Resort. This beautiful property has an origin story that dates back to the 1790s, and is apropriately known as "Vermont's most beautiful address". The property was purchased and renovated by Lawrence Rockafeller, and has earned a reputation as one of the finest resorts in New England.
The Woodstock Inn & ResortWoodstock, USA
With an origin story that dates back to the 1700s, the Woodstock Inn has long been part of the fabric of the village of Woodstock. Completely renovated underr the guidance of Laurance Rockefeller, the resort is an expression of his love of nature and historic preservation. The Woodstock Inn exhudes a timeless elegance, and the facilities and amenities are second to none in the area.
Quechee Gorge; Woodstock
This morning's scenic walk starts from Quechee State Park and along the Quechee Gorge. Formed by glacial activity around 13,000 years ago, the gorge is over a mile long and 165 feet deep. This natural wonder of Vermont is a sight to behold with spectacular views from the trail alongside what is sometimes called "Vermont's Little Grand Canyon."
From the gorge, a short diversion on foot leads us to the Vermont Institute of Natural Science. Located adjacent to Quechee State Park, this 47-acre campus provides a state-of-the-art environmental education facility and wildlife rescue and rehabilitation. It is home to the largest collection of birds of prey in the Northeast, including bald and golden eagles, hawks, owls, and falcons. More than 400 orphaned and injured birds from Vermont and neighboring New Hampshire are treated at the center annually.
Following lunch, we have many options for the afternoon. Depending on your energy level, you may choose to set out on another of our favorite local hikes, return to Woodstock for further exploration, or simply return to the Woodstock Inn to enjoy the impressive amenities of the resorrt.
Dinner will be together at one of the excellent locally-owned restaurants.
Cossingham Road Farm trails; Transfer to Stowe
This morning we say good-bye to our charming inn, and head north towards the village of Stowe, but not without some excursions along the way. We stop in the town of Norwich to walk along the Cossingham Road Farm trails through managed forests and open fields that speak to the farm's agricultural history. Nearly 70 species of birds have been identified by sight or sound on the farm, and if we are lucky, we may see moose tracks or a barred owl along the forested portions of the trail. The contrast of forest and field, ecological and cultural history, and conservation and use makes Cossingham Road Farm a truly unique community resource.
On our drive north, we stop for a fresh lunch at an organic farm stand and enjoy a short, behind-the-scenes tour of the farm before continuing on our drive north.
Next, it's on to Stowe, a village that began as an early 19th-century farming and mill community and gradually evolved into a year-round recreation and vacation destination that attracts visitors from around the world. Our late afternoon is on your own to explore the well-preserved and thriving village that retains the look of its historic role as a market town. Nearly attractions including the Akeley Memorial Building, Vermont Ski and Snowboard Museum, Helen Day Arts Center, and the Stowe History Museum, located in the Stowe Historical Society's one room schoolhouse, provide enriching experiences. You may also choose to enjoy a leisurely walk along Stowe's well-known recreation path, or explore the many unique shops for local crafts, artwork, souvenirs, and Vermont maple syrup.
Dinner tonight is in the cozy dining room of our historic inn.
Green Mountain InnStowe, USA
Visited by U.S. presidents, traded for a farm, home to a railroad company’s offices, site of a grand dance hall, and base for regular Lowell Thomas broadcasts, the Green Mountain Inn has a rich and storied history.
Nestled in the heart of historic Stowe, Vermont, The Green Mountain Inn accommodations are among the finest in Stowe and has captivated travelers from around the world for more than a century. With the perfect blend of classic ambience and modern comforts, the Inn is the ideal location for exploring the area.
Mt. Mansfield; Trapp Family Lodge
For the early risers, we will head out for a pre-breakfast walk. In the morning, there is often mist rising off of the river at this hour, and with the spectacular summer greenery or autumn foliage as a backdrop, it's a picture-perfect and serene setting.
Following breakfast, we gather as a group for a short drive out of town that brings us to Smugglers' Notch State Park. The famous Smugglers' Notch is a narrow pass through the Green Mountains lined with 1,000-foot cliffs. In the earlier days, only a footpath and trail for horses existed here as it was used by many local people who traded illegally with Canada, herding cattle and carrying other goods through the Notch. Later, fugitive slaves used the Notch as an escape route to Canada.
We return to Stowe, and head for the state's highest peak: Mt. Mansfield. We ascend the historic Toll Road by van, and then hike along the ridge to the summit. We are treated to 360 degree views of the Champlain Valley, the Adirondacks, and New Hampshire's White Mountains the entire way.
Descending back towards the village, we stop to enjoy lunch at the Trapp Family Lodge Bierhall. Founded by the famous family of singers who settled in Stowe after fleeing the Nazi occupation of Austria, the lodge offers many walking trails that offer a respite of shade in the summer and highlight the brilliant colors of the foliage in fall. The idea for an on-site brewery began "brewing" in Johannes von Trapp's mind more than a decade ago as a result of enjoying the tasty lager on his trips to the Austrian countryside near his ancestral home.
The afternoon presents a myriad of choices to consider: set out on the trails at the Trapp Family Lodge, further explore the village of Stowe, indulge in a massage at our inn, or simply grab a book and find the perfect reading nook.
Tonight, we dine at one of the best restaurants in the area - Edson Hill.
Shelburne Farms; transfer to airport
This morning we say goodbye to Stowe but make one more special visit before saying our final farewells to Vermont.
Located on 1,400 acres bordering Lake Champlain, Shelburne Farms is a National Historic Landmark that operates as a non-profit educational center promoting sustainability and conservation. Established in 1886 as the agricultural estate of William Seward and Lila Vanderbilt Webb, today, the property hosts community and educational activities throughout the year and is a working farm producing award-winning cheddar cheese and other products that help support the organization. There are many trails on this vast estate, and we may choose to follow one that winds through fields of grazing sheep, past the dairy barn, or towards the elegant lake-side inn.
We enjoy a final lunch together with beautiful views of Lake Champlain and the Adirondack mountains before heading to the Burlington International Airport for journeys home or to other exciting adventures.
Please note that this is a typical itinerary, and actual activities may vary due to weather conditions, local events, and to allow serendipity to play a hand in your experience. Accommodations are as outlined in the itinerary, although we reserve the right to change these or the order visited should the need arise.
5 Days
Sep 29-Oct 3, 2025
Oct 6-10, 2025
From $3,995 Per Person
First two reserved:$695
Additional:$1,195
See single supplement policy below.
MAKE IT PRIVATE
Call for pricing: 1-800-941-8010 or email info@boundlessjourneys.com
SINGLE SUPPLEMENT: Accommodations are based on double occupancy. A single supplement is paid by participants who specifically request single accommodations, subject to availability.
Single Supplement for Scheduled Group Departures. If you reserve at least 120 days prior to departure, you may be eligible for a reduced or free single supplement. This is generally limited to the first one or two solo travelers to reserve, and the reduction is outlined in the pricing for each trip. Free or reduced single supplements are not combinable with other offers or promotions.
If you are traveling alone and wish to share accommodations, we will try to match you with a roommate of the same gender. If you reserve at least 120 days ahead and request a roommate but one is not available, you will receive a $500 reduction from the standard single supplement (unless otherwise noted in the detailed itinerary for your specific trip).
Single Supplement for Custom Tours. Custom Tour prices are generally based on two or more participants; therefore, single supplements for “solo” Custom Tours will vary and are available upon request.
Boundless Journeys' trips are designed for energetic and flexible individuals who like to be active and have a spirit of adventure and a positive attitude. Peak Foliage is rated 2, easy to moderate, on a scale of 1-5 (with 5 being the most strenuous). The walks and hikes on this trip average 2-4 hours in length with minimal vehicle support, on a mix of wooded trails, country roads, and granite ridgelines. While many of the trails we will use will be well-maintained, there will also be rocky sections with uneven footing. Please also refer to the detailed itinerary for descriptions of the activities on each day of the trip.
Your guide(s) will meet you on the first day of the trip at 9 a.m. in the lobby of the Hotel Vermont. Please be dressed for hiking!
Your guides will provide transportation to your choice of Burlington International Airport by 3:00 pm or the Hotel Vemont by 3:30 p.m. Please plan your flight schedule accordingly.
Most Convenient Airport: Burlington International Airport (airport code BTV), Burlington, Vermont
If you plan to drive to Vermont, estimated drive times to Burlington, Vermont are as follows:
New York, NY: 5.5 hours/ 303 milesBoston, MA: 3.5 hours/ 216 milesHartford, CT: 4 hours/ 236 milesPhiladelphia, PA: 7 hours/ 386 milesBuffalo, NY: 7 hours/ 408 miles
It is very important that you realistically assess your physical condition with regard to the demands of this trip. The more well prepared you are for the activities on this trip, the more you will enjoy yourself! Please engage in moderate aerobic activities (walking, jogging, cycling) for at least 30-45 minutes several times a week for 4-6 weeks before the trip. If you live in a flat area, try to incorporate some stairs into your workout, or use a treadmill with varying incline capability. Consult your doctor before undertaking any new fitness program.
As they say in New England, "if you don't like the weather, wait five minutes, and it'll change." The summer can be humid and hot. Cool morning quickly warm up. In fall, mornings are cool, and frost is possible overnight in early October. Average high temperatures are quite comfortable for hiking, although dressing in layers is essential to your comfort throughout the day. Rain is possible at any time, and weather conditions can change rapidly in the mountains, so having rain gear on hand is also advisable.
You may obtain more detailed weather information on www.weatherbase.com.
Stowe
High: 78 Low: 55
High: 68 Low: 45
Woodstock
High: 81 Low: 55
High: 71 Low: 45
Each season brings its own highlights to Vermont. Summer offers the warmest weather and typically the driest trail conditions, while fall offers the stunning displays of color. The exact days of peak foliage vary from year to year and from location to location throughout the state. However, we choose our dates for their reliability for having amazing color, often accompanied by great hiking temperatures and blue skies.
With a Boundless Journeys guide, your experience is that of friend and local adventurer. We believe strongly in working with local guides, experts in the areas to which we travel, and they hold the keys to unlocking the hidden delights of your chosen destination. Although you will never know they are at work—the mark of a truly great leader—our guides make magical things happen and add a dimension to your trip that you could not experience on your own. Over the years we have forged bonds with some of the best guides in the world, and we typically work with a small team of guides in each region. You will be informed of the guide for your trip one month prior to your departure.
Each season in Vermont brings a plethora of adventures and colors to the landscape — pristine white fields and snow-capped pine trees in winter, the pastels of wildflowers and lilacs in spring, deep greens of lush forests in summer, and...
Hiking on trails, country roads, and village streets 1-4 hours per day and up to 4 miles.
This trip can be your own adventure by taking over one of our scheduled dates, or we can request a fresh one.
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