Vermont Relaxed Hiking Adventure During Fall Foliage

“Thousands of tired, nerve-shaken, over-civilized people are beginning to find out that going to the mountains is going home; that wildness is a necessity.”

John Muir, 1901

That quote from 1901 was probably true when John Muir said it but it certainly seems accurate now.

Vermont is a sparsely populated state full of forests, mountains, charming towns, and friendly people. The state is especially beautiful in mid-October when fall foliage is in full display. Vermont truly is the most spectacular for hiking in the entire east coast.

Our hikes are all excellent but moderate in difficulty level, making this tour perfect for someone who wants to get into the woods, work out a bit, and reach a scenic destination but probably is not ready for peak bagging in Colorado. We hike on the beautiful grounds of the Von Trapp Family Resort and can tell why they chose this place for their home after fleeing Austria. We hike on top of Mount Mansfield, the state’s highest peak, with a vehicle assist to the top. We take a path through the Moosalamoo Forest up to and around Silver Lake, which is perfect for a quick swim if you bring your suit. We venture on a portion of the wonderful Trail Around Middlebury (MAP), a 19-mile trail that circles the city.

We have selected two fantastic small towns for our overnights. Stowe is Vermont’s leading mountain resort, famous for its winter skiing and its summer hiking. It also has a ton of restaurants, several breweries, and many small shops. Middlebury is Vermont’s most famous college town, host to Middlebury College, and thus has a restaurant and nightlife scene that supports students and professors alike.

Join us in Vermont for a fantastic fall getaway and make John Muir proud!

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Trip Highlights

  • Hike on top of Mount Mansfield with views on all sides from Vermont's highest point.
  • Hike through the 2,500 acres of the Trapp Family Lodge property
  • Check out the seven beer, wine, spirits, and cider makers on the Middlebury Tasting Trail
  • Explore a portion of the 19-mile Trail Around Middlebury and then enjoy the attractions of this college town
  • Enjoy Vermont's hippest mountain town, Stowe, famous for its skiing in winter and hiking in summer
  • Be amazed by the beautiful fall foliage colors!

We meet in Burlington after lunch and shuttle to the gorgeous mountain town of Stowe, less than an hour away. For those of you driving, we can meet directly in Stowe. Arriving in Stowe, we’ll stop in the heart of the village at the trailhead to the Sunset Rock Trail, a short but scenic hike up a small hill. At the top, there is a beautiful grassy glen where we'll have introductions and talk a bit about the upcoming tour. For those interested in more mileage, hike another two miles on the Stowe Recreation Path, a 5.3 mile paved trail that winds through town and is a perfect example of how a paved trail can be such an addition to a local community. The path will take us to our hotel where we’ll check in before heading out for dinner at Tres Amigos, a fun Mexican restaurant that happens to be right next to Stowe Cider. Distance: 4 Miles


This morning we’ll drive a short distance to Stowe Mountain Resort on the slopes of Mount Mansfield, the highest point in Vermont and one of the few places in the state with a true alpine environment. We'll then take the winding road to the top of Mount Mansfield and hike along the ridge top of Vermont's highest peak. The four-mile hike is moderate in difficulty but has the best views in Vermont! For those interested, you can add a two-mile hike up the mountain from the base. In the afternoon we'll have time to explore town, perhaps visit a local covered bridge or maple syrup farm, or hang out at the pool before having a beer at Vermont's most famous brewery, Alchemy Brewing, followed by dinner. Distances: 4 or 6 miles


This morning after breakfast we’ll check out and drive to the Trapp Family Lodge. Set on 2,500 acres and with 62 miles of trails, the lodge is the family home of the famous Von Trapp family that fled from Austria and was immortalized in the Sound of Music. We have several walking options, including a moderate six-mile hike to Slayton Pasture Cabin or several shorter, flatter options. Lunch is on your own at the Trapp Family German-style restaurant. After lunch, we’ll continue our journey by taking a beautiful 1.5 hour drive to Middlebury, crossing the beautiful Green Mountains on the spectacular Lincoln Gap Road. Middlebury is Vermont’s most famous college town, where we’ll check in to our lodgings and have time to shower and rest before heading out to dinner. Distances: 6 Miles


Today we head to the Moosalamoo Forest for a hike to Silver Lake. The trail is mostly uphill but at a gradual incline. We pass Lana Falls, a series of cascades that are used for hydroelectric power, and Lenny's Lookout that provides a view over the Champlain Valley below. Upon reaching Silver Lake, you can choose to jump in the cool waters (if you brought a suit) or hike on a trail that loops for 2.5 miles around the lake. Back in Middlebury, you’ll have time to explore town and in the evening we’ll have our farewell dinner at Morgan's Tavern, the onsite restaurant of our inn. Distances: 3 or 6 Miles


After breakfast, we’ll walk on a portion of the Trail Around Middlebury (TAM), an amazing asset for this small college town. The 19-mile trail loops around the town, something we wish every town and small city would have. We’ll walk three miles of the trail, up and over Chipman Hill, on a forested trail. We’ll return to the inn to shower, check out, and say our goodbyes. You can then catch our shuttle back to Burlington or drive back home or further on your adventures. Distance: 3 Miles

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Trip Accommodations


The Sun & Ski Inn is located in the heart of Stowe, considered Vermont's mountain town. Rated #3 in Stowe on Trip Advisory (which is filled with high-end properties), this contemporary and casual option is full of amenities including miniature golf, an indoor pool and hot tub, and even a bowling alley onsite! With plenty of restaurants and shops, a river that runs right through town, and mountains (including Vermont's highest peak) above, Stowe has something for everyone.


An historic hotel dating from 1827, the Middlebury Inn is located right in the center of town at Court Square and is the perfect place for hanging out on the front porch and watching Middlebury go by. You can also not get a more convenient location for exploring Middlebury. We'll eat one dinner at Morgan's Tavern, the inn's restaurant.

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Arrival & Departure

If you are driving to the tour, we will meet you in the early afternoon in Stowe, Vermont. You will need to make one shuttle mid-trip from Stowe to Middlebury. If you are flying to the area, we will pick you up at the airport in Burlington and drop you back off on the last day of the tour.

What's Included?
  • At least one Zephyr guide accompanies each trip and a second is added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All of your dinners and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.

The summer season in Vermont runs from about mid-May through mid-October, so we are at the very tail end of the hiking months. The average daytime high in Stowe will only be in the upper 50s and it is possible to get snow overnight. Middlebury will be a bit warmer. However, the cold nights are what produces the fall foliage, and we will happily wear a hat and extra layer to take in the majestic colors.

Extending Your Stay

You will need a car if you wish to extend your stay in the area. Since fall is peak season, we suggest you make hotel reservations in advance. We don't spend any time in Burlington, which is a fun city worth spending a night or two. There are many other cute, small towns in the state!

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.

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