Vermont: Fall Foliage

Waitsfield Common Road; 2-3 miles, easy

Country Walkers Pre-Tour Extension Guests:
Following an included breakfast, please meet your Country Walkers leaders and fellow travelers at 9:00 a.m. in the lobby. Your leaders will be wearing Country Walkers shirts for easy identification.

Country Walkers Tour-Only Guests:
Your leaders will meet you at our pre-tour hotel—the Courtyard Burlington Harbor Hotel in Burlington, Vermont—at 9:00 a.m. in the lobby. You may take a bus, rideshare, or taxi from Burlington International Airport to the hotel. They’ll be wearing Country Walkers shirts for easy identification. Please be dressed for walking: comfortable, weather-appropriate attire, sturdy footwear, and a daypack (to carry essentials such as rain gear and a water bottle) are required.

After a brief orientation meeting, you depart for an introductory walk in the town of Waitsfield, located in the heart of Vermont’s Mad River Valley. Situated 40 miles from Burlington and home to just 1,700 full-time residents, Waitsfield is known for its natural beauty and proximity to two popular ski destinations: Sugarbush Resort and Mad River Glen. It also boasts charming restaurants and a 100-year-old covered bridge.

Today’s walk follows a classic country road with magnificent views over the Mad River Valley toward Sugarbush. Along the way, you’ll visit two notable highlights: the von Trapp Greenhouse and Farm and the 1891 Skinner Barn. You’ll end your walk at the intersection with East Warren Road, where you’ll board a van for a short drive to today’s lunch spot.

Hearty Vermont pub fare served in a lively local taproom provides a relaxed midday break in a casual, welcoming atmosphere.

After lunch, you depart for a one-hour and 15-minute drive to the quintessential New England town of Woodstock. Nestled in the beautiful Green Mountains, Woodstock is known for its storybook charm, featuring an iconic covered bridge and a classic village green.

Your final destination today is one of the town’s most delightful inns, your home for the next two nights. Tucked just outside Woodstock, this boutique, family-owned property is set on six acres of stunning riverside grounds. Soak in the surrounding nature and Vermont charm from the riverside rocking chairs or balconies. After time to freshen up, you may enjoy a Vermont-made aperitif before dinner at the inn, where you’ll choose from a menu highlighting fresh, locally sourced ingredients.

Included Meals: Lunch, Dinner

The Pogue and King Farm; 4.5 miles, easy to moderate, 550-ft. elevation gain and loss OR Mt. Tom; 4.5 miles, moderate, 650-ft. elevation gain and loss

After a hearty country breakfast buffet—featuring fresh pastries, eggs, coffee, and more—you’ll set off for a full day of exploration in and around Woodstock. The day begins with a short five-minute drive to Marsh-Billings-Rockefeller National Historical Park, a site with a rich legacy of conservation and land stewardship. Once the estate of early environmentalist George Perkins Marsh, and later home to Frederick Billings and the Rockefeller family, the park showcases historic woodlands, scenic carriage roads, and sweeping views of the surrounding Green Mountains.

You’ll have two walk options this morning. The easier option follows a gently rolling trail from the Carriage Barn Visitor Center through mixed hardwood forest to The Pogue, a peaceful 14-acre mountain pond. From there, continue on to King Farm, a quiet meadow with lovely views, before looping back. The path is mostly shaded and well-maintained, offering a relaxed pace with mild elevation changes. The second option is a more moderate hike to the summit of Mt. Tom. This route ascends steadily via historic carriage roads, winding through forested terrain to reach a viewpoint that looks out over the village of Woodstock and the broader valley below. A different trail leads back down, creating a satisfying and varied loop.

After your walk, enjoy a scenic picnic lunch on the park grounds. You’ll then have time to explore the Billings Farm & Museum—a working dairy farm and engaging heritage site—and browse the exhibits at the Carriage Barn Visitor Center, which sheds light on the park’s legacy and the families who shaped it.

Later this afternoon, return to downtown Woodstock for time at leisure. Spend the rest of the day as you wish—meandering through the town’s charming streets, browsing local shops, cafés, and art galleries. Delve into local history at the Woodstock Historical Society, founded in 1929, or visit Simon Pearce, a 19th-century mill and glassblowing studio perched above a scenic waterfall. You may also wish to stop by Gillingham’s—the oldest store in town—for classic Vermont goods and souvenirs.

Dinner is on your own this evening in downtown Woodstock. Choose from a variety of restaurants, each offering its own distinctive character and seasonal Vermont flavors. Many Country Walkers guests have enjoyed dining at The Red Rooster. We highly recommend making dinner reservations in advance of your walking tour.

Included Meals: Breakfast, Lunch

VINS; 1 mile, easy. Quechee Gorge; 2 miles, easy to moderate

A 20-minute drive from the hotel brings you to the Vermont Institute of Natural Science (VINS) Nature Center, a leading hub for wildlife education and environmental stewardship. Nestled in the forest canopy, the center invites you to stroll along a mellow one-mile Forest Canopy Walk, elevated above the forest floor and offering treetop views of the surrounding landscape. Along the way, interactive exhibits highlight the importance of native habitats and spark a deeper appreciation for Vermont’s natural world. Your visit concludes with a live raptor show, where expert educators introduce you to native birds of prey—such as owls, hawks, and falcons—and share insights into their behavior and critical role in the ecosystem.

Just down the road, you’ll explore Quechee Gorge, one of Vermont’s most dramatic natural landmarks. Often referred to as the state’s “Little Grand Canyon,” this striking 165-foot-deep chasm was carved by glacial activity approximately 13,000 years ago. You’ll descend into the gorge and follow a peaceful trail along the Ottauquechee River, surrounded by forested cliffs and cascading water. Above the gorge, several casual restaurants and cafés near the visitor center offer options for lunch on your own.

Following your discoveries, a 90-minute drive brings you to the charming mountain town of Stowe, where wooded trails await and spectacular views abound. Your home for the next three evenings is an inn nestled in the heart of Stowe Village, surrounded by the Green Mountains. Here, cozy comforts welcome you, with Vermont-crafted furnishings and authentic New England charm. Like many inns in this region, this one is deeply connected to the story of Vermont—its natural beauty, railroads, and evolving industries. Splendid cuisine greets you at the end of your active day.

Included Meals: Breakfast, Dinner

2-4 miles, easy to moderate OR Mt. Mansfield Ridgeline; 3 miles, moderate to challenging

This morning, you drive through Smugglers’ Notch, a dramatic, narrow mountain pass nestled between Mt. Mansfield and Sterling Peak. Towering cliffs and massive boulders flank the winding road, creating a rugged and scenic corridor. The Notch earned its name in the early 1800s, when smugglers used the remote passage to transport illegal or embargoed goods to and from Canada—first during the Embargo Act of 1807 and later during Prohibition.

Today is devoted to exploring the trails in and around the iconic mountain town of Stowe. Depending on conditions, you may choose to walk on the expansive trail network at the Trapp Family Lodge or venture to the base—or even the summit—of Mt. Mansfield, Vermont’s highest peak. Ascending Mt. Mansfield by van along the scenic Stowe Mountain Toll Road, you reach the Visitors’ Center and enjoy a short walk to a viewpoint offering sweeping 360-degree vistas. Those who wish to continue can follow the Ridge Trail along the summit, which is part of the Long Trail—the nation’s first long-distance hiking trail. Country Walkers is proud to support the Green Mountain Club, stewards of this iconic 270-mile route. This alpine section features rare arctic-alpine flora—such as diapensia, alpine sandwort, and bearberry willow—and views that stretch to the Adirondacks, the White Mountains, and even Mount Royal in Canada on a clear day.

Alternatively, at the Trapp Family Lodge, you may explore a vast network of over 30 miles of trails that crisscross the property’s 2,500 scenic acres. Founded by the von Trapp family—whose story was immortalized in The Sound of Music—the lodge blends Austrian heritage with Vermont hospitality. Trails range from forested paths to wide open meadows with peaceful mountain views.

Lunch today is served at the lively von Trapp Bierhall, where traditional Vermont and Austrian dishes are paired with the family’s own craft-brewed lagers.

Later in the afternoon, you’ll have time to explore Stowe Village at your own pace. Enjoy a stroll along the scenic Stowe Recreation Path, stop into local shops or galleries, or simply relax and soak in the charm of your inn. Dinner is on your own this evening, with many restaurants located within easy walking distance. Your leaders will be happy to help with recommendations.

Stowe is more than just a ski town—this vibrant New England village offers a delightful blend of outdoor adventure, cultural attractions, and small-town charm. From craft breweries and fine dining to boutique galleries and mountain views, Stowe captures the spirit of Vermont in every season.

Included Meals: Breakfast, Lunch

4 miles, easy

This morning’s walk takes you to beautiful Bull Moose Pasture, a quiet, scenic stretch of Vermont countryside offering wide-open views and a tranquil sense of place. Along the way, your leaders share insights into the art of maple sugaring—how Vermont’s iconic syrup is made from tree to table—and reveal little-known stories about the area’s unique political past. As you walk, admire the pastoral landscape: working farms, stands of stately sugar maples, and meadows dotted with iconic black-and-white Holstein cows—quintessential scenes of rural Vermont.

In the afternoon, you’re welcomed by George Woodard, a third-generation organic dairy farmer, maple sugarmaker, and beloved local storyteller. With warmth and humor, George shares firsthand accounts of the joys and challenges of farming in Vermont, offering a deeper understanding of the state’s rich agricultural heritage. You’ll board a hay wagon for a relaxed ride through his meadows, passing weathered barns and hillside pastures as you take in sweeping views of Camel’s Hump—Vermont’s third-highest and most iconic peak, recognizable by its distinctive silhouette.

This evening, you gather for a festive farewell dinner, raising a glass to your Green Mountain adventure. Afterward, you may wish to enjoy a quiet swim beneath the stars in the hotel’s heated outdoor pool.

Included Meals: Breakfast, Lunch, Dinner

2-3 miles, easy

After breakfast, you depart Stowe for historic Shelburne Farms, a nonprofit education center for sustainability located on the shores of Lake Champlain. Spanning 1,400 acres and designated a National Historic Landmark, the farm was established in 1886 as the agricultural estate of William Seward and Lila Vanderbilt Webb. Today, this working farm and campus blends environmental education with sustainable agriculture, offering a rich array of community programs, a working dairy, and hands-on learning opportunities.

The property is home to more than 100 Brown Swiss cows, a farmstead cheese-making facility, a seasonal inn housed in the original Webb family home, and an expansive organic market garden. As you explore the grounds along a network of scenic trails, you’ll pass the stately inn, the architecturally impressive Coach Barn, and the historic Farm Barn, where the dairy and creamery are located. Panoramic views of Lake Champlain and the Adirondack Mountains provide a stunning backdrop and a lasting visual memory of your time in Vermont.

Following a final picnic lunch, you travel to Burlington International Airport or to the Courtyard Burlington Harbor Hotel, where you bid farewell to your leaders and continue your onward travels. The tour concludes at approximately 3:00 p.m. at the airport and 3:30 p.m. at the Courtyard hotel.

Included Meals: Breakfast, Lunch

Waitsfield Common Road; 2-3 miles, easy. Cossingham Road Farm Loop; 2-3 miles, easy

Your leaders will meet you at the Courtyard Burlington Harbor Hotel at 9:00 a.m. in the front lobby. They’ll be wearing Country Walkers shirts. Please be dressed for walking.

After a brief orientation meeting, you depart for an introductory walk in the town of Waitsfield, located in the heart of Vermont’s Mad River Valley. Situated 40 miles from Burlington, and with only 1,700 full-time residents, Waitsfield is known for its natural beauty and two popular ski destinations: Sugarbush Resort and Mad River Glen. It also boasts numerous restaurants, a 100-year-old covered bridge, and The Big Picture Theater & Café (a quirky theater-restaurant famous for its maple donuts).

Your first walk today takes you along a classic country road with magnificent views over the Mad River Valley toward Sugarbush. On your walk, you will also enjoy two notable highlights: the von Trapp Greenhouse and Farm and the Skinner Barn. The Skinner Barn is a beautifully restored historical post-and-beam dairy barn originally built in 1891 by the Daniel Skinner family. You end your walk at the intersection with East Warren Road, where you board a van for a short drive to today’s lunch spot.

After lunch, you depart for a one-hour drive to the quintessential New England town of Norwich. With a population of just over 3,400, Norwich has a vibrant downtown, a lovely village green, and the memorable Dan & Whit’s general store, whose motto is “If we don’t have it, you don’t need it!”

This afternoon’s walk is at the Cossingham Road Farm, where you embark on a meandering walk through woods and open fields. Nearly 70 species of birds have been identified by either sound or sight on the farm, and if you’re lucky, you may spot a barred owl or moose tracks.

Your final destination today is one of the town’s most charming inns, your home for the next two nights. Steeped in New England character, it has been a fixture of Norwich since its early days as a tiny Vermont village. Its Victorian architecture, antique furnishings, and distinctive historic features date back almost to the American Revolution, but you’ll enjoy all the amenities of a modern hotel. After time to freshen up, you may enjoy a Vermont-made aperitif before dinner at the inn, where you choose from their menu featuring dishes made from fresh, local ingredients.

Included Meals: Lunch, Dinner

Optional self-guided history walk; 1 mile, easy. Union Village Dam; 3 miles, easy to moderate

Early risers may opt for a brief self-guided history walk along Norwich’s Main Street before breakfast at the inn’s terrace dining room. Following this refreshing start to your day, you depart for a walk along the Ompompanoosuc River, eventually reaching the Union Village Dam. The dam was built in 1950 as part of a system of 16 dams and reservoirs to control flooding along the Connecticut River and its tributaries. This walk offers a window into the history of Vermont’s industries, as you pass the foundation of an old woolen mill and the sites of former farms and homesteads. A multitude of birds and other wildlife inhabit the mature hardwood forest surrounding the dam.

Next, a short but scenic drive brings you over a covered bridge into Thetford, a town made of six villages lining the Connecticut River. The town is home to the nation’s oldest secondary school, Thetford Academy. In East Thetford, you visit the Cedar Circle Farm—an organic farm and education center whose mission is to raise awareness about the importance of local agriculture and increase access to affordable healthy produce. After a private farm tour, you enjoy a picnic lunch provided by your leaders.

Tonight’s dinner is on your own in nearby Hanover, New Hampshire (a short five-minute drive from your accommodation).

Included Meals: Breakfast, Lunch

2 miles; easy to moderate. Optional Mt. Tom; 2 miles, easy to moderate

A 15-minute drive from Norwich brings you to Vermont’s “Little Grand Canyon”—the 165-foot-deep Quechee Gorge. Here, you descend into the gorge and walk along the Ottauquechee River. After, a short drive brings you to the charming village of Woodstock. Voted the prettiest town in America, Woodstock boasts a covered bridge and a village green surrounded by restored Georgian, Federal-style, and Greek revival homes. There is also a unique selection of museums, including the Billings Farm & Museum, the Marsh-Billings-Rockefeller National Historical Park, and The Woodstock Historical Society. Here, you have free time to enjoy the local cuisine; wander over to Gillingham’s, the oldest store in town; or partake in an optional Mt. Tom walk, located in one of the oldest professionally managed woodlands in America.

Voted the “prettiest town in America,” Woodstock is a pleasure to explore on foot. A free afternoon invites you to embark on an activity of your choice. For lunch on your own, choose from one of the many restaurants in town or perhaps pack a picnic lunch to eat trailside.

Following your discoveries, a 90-minute drive brings you to the classic mountain village of Stowe, where wooded trails welcome and spectacular views abound. Your home for the next three evenings is an inn situated in the heart of Stowe village, amid the Green Mountains. Here, cozy comforts offer a warm welcome amid Vermont-crafted furnishings and New England charm. Like so many inns in this region, this one has been inextricably tied to the story of Vermont – its nature, its railroads, its growth through industry. As a guest, it is a privilege to join the ranks of the diplomats, titans, and simple New Englanders who have stayed here. Splendid cuisine greet you here at the end of your active day.

Included Meals: Breakfast, Dinner

2-4 miles, easy to moderate OR Mt. Mansfield Ridgeline; 3 miles, moderate to challenging

This morning, you drive to Smugglers’ Notch—the deep, boulder-laden passageway between Mt. Mansfield and Sterling Peak. Smugglers’ Notch got its name in the early 1800s when it was used for transporting illegal or embargoed goods in and out of Canada.

Today is devoted to exploring the trails in and around the town of Stowe, either at the Trapp Family Lodge or around the base or the summit of Mt. Mansfield (conditions permitting). After ascending Mt. Mansfield by van via the winding Stowe Mountain Toll Road, you admire breathtaking views of the surrounding valleys during a brief stroll from the Visitors’ Center to a viewpoint offering sweeping 360-degree vistas. Those choosing to continue to the summit of Mt. Mansfield walk along the ridge, taking in a panorama of Lake Champlain and several mountain ranges, including the Adirondacks in New York, the White and Green mountains of New Hampshire and Vermont, and Mount Royal in Canada.

At Trapp Family Lodge, the walking choices are nearly infinite, as their 2,500 acres boast over 30 miles of hiking trails, which double as cross-country ski trails in winter. The lodge was founded by the famous family who settled in Stowe after fleeing the Nazi occupation of Austria. You enjoy lunch at the lively Bierhall, where its namesake beer is brewed and both Vermont and Austrian specialties are on the menu.

Later in the afternoon, there is time to explore the village of Stowe. Take a stroll along its recreation path, or simply relax and enjoy the tranquility of your inn. Tonight, you have dinner on your own, choosing from the many local restaurants within easy walking distance of your accommodation. Your leaders will be happy to assist in your choice.

Another charming New England town, Stowe is more than just a ski town—it also boasts an abundance of art galleries, craft breweries, and excellent dining options.

Included Meals: Breakfast, Lunch

4 miles, easy

This morning’s walk takes you to beautiful Bull Moose Pasture. On your way to the pasture, your leaders share secrets about the art of maple sugaring and tell tales of the little-known political history of the area. Admire the view as you pass working farms, sugar maple groves, and meadows dotted with Vermont’s ubiquitous Holstein cows.

In the afternoon, you visit with George Woodard, a third-generation Vermont organic dairy farmer and storyteller. From George, you gain a better understanding of Vermont’s history of dairy farming and maple sugaring. Take a hayride through his meadows, where you’ll have views of Camel’s Hump, Vermont’s third-highest peak. This evening, you gather for a final dinner, where you toast your Green Mountain adventure, and perhaps enjoy a post-dinner swim in the hotel’s heated outdoor pool.

Included Meals: Breakfast, Lunch, Dinner

2-3 miles, easy

After breakfast, you depart Stowe for historic Shelburne Farms, a nonprofit center promoting sustainability and conservation. Comprised of 1,400 acres on the shores of Lake Champlain, and designated a National Historic Landmark, the farm was established in 1886 as the agricultural estate of William Seward and Lila Vanderbilt Webb. Today, this working farm integrates a host of community and educational activities with a working dairy. The property is home to more than 100 Brown Swiss cows, a cheese-making facility, a seasonal inn, and an organic market garden.

Choosing from numerous trails, you explore the grounds and take in the incredible vistas, while passing by the elegant inn as well as the dairy and coach barns.  Dramatic views of Lake Champlain and the Adirondack Mountains leave a lasting impression of your visit to Vermont.

Following a final picnic lunch, you travel to the Burlington International Airport or to the Courtyard Burlington Harbor Hotel, where you bid farewell to your leaders before you continue your onward travels.

Included Meals: Breakfast, Lunch