If your idea of the perfect New England vacation includes scenic country roads, charming small towns, cozy inns, and plenty of good food, the Vermont Inn-to-Inn Walking Tour might be exactly what you’re looking for. My husband and I wanted an active vacation with a comfortable bed and a great meal at the end of the day, so this self-guided walking tour sounded like the perfect combination. 

In this review, I’ll share our thoughts on each day’s itinerary and the Inns we enjoyed. Then I’ll share thoughts for future trips based on our experience. Read on for all the details and watch the video below to see some of the scenery and inns.

Vermont Walking Tour Basics

Over four days, we walked from one Vermont village to the next, following quiet back roads and wooded paths through the countryside while our luggage was transported ahead to our next inn. Each afternoon, we arrived to a warm welcome, a comfortable room, and a generous snack—with nothing left to do but relax. In the evening, we were served a home-cooked dinner and given details about the next day’s walk.

The tour revolves around four fantastic inns nestled in the foothills of Vermont’s Green Mountains. Each has its own personality, but the basics are the same: welcoming hosts, comfortable accommodations, and plenty of good food, including breakfast, afternoon snacks, and a three-course dinner. Each evening, the innkeepers also provide a briefing on the following day’s walk, including detailed directions and anything you need to know about the route.

The four-night walking tour begins on Sunday, with a different group of walkers starting at each inn and then rotating among them. That means your exact itinerary will depend on where you begin. Ours was Chester → Proctorsville → Ludlow → Weston → Chester.

The daily walks range from about 8 to 12 miles, primarily over rolling hills, although there is one sustained climb from Proctorsville to Ludlow. You don’t need to be an experienced hiker, as most of the walking is along quiet country lanes and forest roads, primarily on gravel and dirt surfaces. You’ll carry a day pack with water and snacks provided by the inns and navigate using a map and simple written directions provided the night before. The tour is self-guided so once you’re on the trail, you walk at your own pace and can stop for breaks whenever you like. On two days, you walk directly from the inn, so you can choose your own starting time. On the other two, everyone leaves the inn together for a shuttle to the starting point, but once you arrive, you’re free to walk at your own pace.

Arrival Day in Beautiful Vermont

We arrived at the beautiful Inn Victoria on Main Street in the charming village of Chester, Vermont, on Sunday afternoon. Dating back to the 1850s, this elegant Victorian bed-and-breakfast is filled with period antiques and historic charm, but offers modern comforts throughout. Each guest room is uniquely decorated, and ours featured a claw-foot bathtub and an especially comfortable bed. After a warm welcome, a tour of the property, and settling into our room, we headed out to explore the town. We enjoyed a leisurely walk through the historic cemetery and along a nearby nature trail before returning to the inn for dinner.

Dinner was a wonderful introduction to the hospitality we would enjoy throughout the trip. We had a choice of two entrées: Sean selected the fish, while I opted for pasta. Both were delicious, but the highlight was the starter—a pumpkin soup that stole the show! After dessert, we all gathered in the sitting room for our first “walk talk.” Our hosts provided maps and detailed directions, walking us through everything we needed to know for the following day’s route. After a cozy night’s sleep, we enjoyed a hearty breakfast and selected snacks to carry along on our first day of walking.

Day 1: Chester to Proctorsville

Our first day of our Vermont Inn to Inn Walking Tour, we began right outside the front door of Inn Victoria. We made our way through the charming village of Chester before heading into the countryside toward Proctorsville. The route followed quiet country roads through rolling hills and included a beautiful stretch through Proctor Piper State Forest. My fitness app recorded just over 12 miles and 1,385 feet of elevation gain, making this a substantial first day of walking. Fortunately, the peaceful scenery and changing landscapes made the miles enjoyable.

Our home for the night was the Golden Stage Inn, a charming country bed-and-breakfast with a welcoming front porch, outdoor swimming pool, and beautiful grounds. Innkeeper Julie greeted us with a delicious charcuterie plate, which I promptly devoured poolside before taking a refreshing swim. After a warm day of walking, that pool was definitely the highlight of my afternoon! Sean preferred relaxing on the front porch, writing in his journal and watching the occasional car pass by.

That evening, we enjoyed another fantastic three-course dinner, followed by a thorough “walk talk” to prepare us for the following day’s route. After a restful night’s sleep, we started the morning with a hearty breakfast, made even more special by honey harvested from the inn’s own beehives. I even bought a bottle to take home. With our snacks packed and another day of exploring ahead, we were ready to hit the road.

Day 2: Proctorsville to Ludlow 

Our second day took us from Proctorsville to Ludlow via the scenic Pinnacle overlook. About two hours into the walk, it started raining, but the temperatures were mild, and we actually found the rain refreshing. The timing couldn’t have been better, as we were a little more than halfway up a steep climb our innkeeper had warned us was known as “Heartbreak Hill.” Despite the rain, we still enjoyed beautiful views from the Pinnacle before descending toward Ludlow. By the time we reached our next inn, my fitness app had a smidge under 11 miles and 1,143 feet of elevation gain.

Our home for the night was the Governor’s Inn, the grandest of the four inns we visited. This elegant historic mansion has an impressive exterior and beautifully appointed interiors that feel more formal while still welcoming and comfortable. Innkeeper Craig greeted us warmly with another delicious afternoon snack, a tradition we were quickly growing to appreciate!

After settling into our spacious, well-appointed suite, I headed out to explore Ludlow, a historic Vermont town where future President Calvin Coolidge attended high school. Meanwhile, Sean opted for a nap, lulled to sleep by the sound of rain falling on the skylight above our room.

That evening brought another wonderful three-course dinner and an informative “walk talk” about the next day’s route. After a comfortable night’s sleep and a filling breakfast, we packed our snacks and headed out for another day of exploring Vermont’s countryside.

Day 3: Ludlow to Weston 

Day three was our easiest walk, but also one of the most memorable. We started with a van ride from the Governor’s Inn to Weston Priory, a Benedictine monastery tucked into the Vermont countryside. After spending some time exploring its beautiful, peaceful grounds, we set off along quiet backroads toward the historic village of Weston.

Just before reaching town, I couldn’t resist cooling off in a waterfall, and Sean and I enjoyed a relaxing break beside the creek. Once in Weston, we wandered around the historic village square, explored the Old Mill, and browsed the local shops. We also stopped for lunch and treated ourselves to maple creemees at the iconic Vermont Country Store—a quintessential Vermont experience! By the time we reached our next inn, we’d walked 8 miles with just 541 feet of elevation gain, making this a wonderfully relaxed day with plenty of time for sightseeing.

Our home for the night was the Coho Inn, a cozy, slightly quirky property with a relaxed atmosphere that immediately made us feel at home. After another delicious dinner and our evening “walk talk,” we headed downstairs to the inviting great room, where comfortable furnishings and a collection of board games encouraged guests to settle in and stay awhile. We enjoyed conversation and a board game with some of the other walkers before retiring to our comfortable room for another restful night’s sleep.

Day 4: Weston to Chester

For our final day, we were once again shuttled to the starting point. Knowing it was our last walk together, everyone started out as a group, enjoying a little more conversation before gradually spreading out as we settled into our own pace. The route was wonderfully peaceful, following quiet backroads and wooded paths through the Vermont countryside. We covered just under 11 miles with 745 feet of elevation gain before crossing a suspension bridge into Chester. From there, we practically dragged our feet back to Inn Victoria, where our car and luggage were waiting. We simply weren’t ready for this wonderful adventure to end!

It turned out to be one of our favorite trips, and a wonderful way to experience a quieter, slower-paced side of Vermont.

Similar Trips for the Future 

We’ve taken plenty of wonderful vacations over the years, but this mix of scenic walks, charming inns, delicious food, and the freedom to explore at our own pace is one we’ll definitely seek out again.

One unexpected pleasure of the Vermont Inn-to-Inn Walking Tour was meeting other travelers who shared our love of active vacations. Over dinner and during our evening gatherings, we swapped stories and recommendations for future adventures. Several fellow walkers suggested the Camino de Santiago in Spain, Scotland’s West Highland Way, and the Island Walk on Prince Edward Island, Canada.