Explore Southern Vermont on a four-night, self-guided walking tour connecting four distinctive, independently owned inns. Follow quiet country roads through historic villages, past farms, forests, and rolling hills, enjoying the scenery at your own pace.

Along the way, enjoy welcoming accommodations, dinner and breakfast at each inn, and the personal touches that make every stay different. We transfer your luggage between inns and provide maps, route notes, and support throughout your tour, leaving you free to enjoy the walk and discover this beautiful corner of Vermont.

Inn Victoria offers a charming stay in the heart of Chester, with easy access to local attractions. Guests will appreciate the delightful Victorian architecture and individually decorated rooms. Enjoy a delicious complimentary breakfast made with local ingredients, and unwind in the beautifully landscaped gardens. The on-site hot tub adds an extra touch of relaxation to your stay.

Enjoy a home-cooked 3-course dinner

Each morning you’ll be greeted with a full, hearty breakfast.

Before you head out for your walk, you’ll be given ample trail snacks to keep you energized for your walk.

13-Mile Walk

A 13-mile walk through three distinctly different terrains; this delightful experience will take you through the Historic Chester Village, an enchanted valley filled with large boulders on all sides, and through the very special Proctor Piper Forest.

As you depart Inn Victoria’s front door you will immediately fall in love with Chester Village historic treasures such as the 250-year-old cemetery, train station & stone village.  Leaving the village behind you will cross country into the Chester forest where the old rock walls are dominant features and the old gravel road is shaded by trees.  With Dean brook to your right and large boulders all around this enchanting stretch, watch for the tree growing directly from the center of a large boulder!  Your final stretch will take you through a moderate rise through the peaceful and cool expanse of the Proctor Piper Forest approaching the Black River to the Village of Proctorsville.

Enjoy a home-cooked 3-course dinner

Enjoy a typical Vermont country breakfast each morning prepared for you by our innkeepers.

10.7 miles

This walk begins through the small village of Proctorsville, passing the town’s post office, church, library and elementary school, and becomes more rural as you leave the village behind (and below).  As you ascend the hill and the pavement turns to a dirt road, your efforts will be rewarded with grand views of the pastoral and mountain landscapes surrounding you.  A visit to the area the locals call The Pinnacle offers you a spot to relax and enjoy your snacks while absorbing the stunning world around you. Then you’ll descend the other side of North Hill, barely noticing at first that your surroundings are transforming from rural to village once again.  You will emerge in the village of Ludlow, where you can take your time to browse the shops, galleries, and pubs, or you can head directly to the next inn of your tour where its promised comforts await you.

Enjoy a home-cooked 3-course dinner

Enjoy a typical Vermont country breakfast each morning prepared for you by our innkeepers.

In order to keep this walk manageable, you will be driven to a starting point about 10 minutes from The Governor’s Inn. This ride takes you from Ludlow over "Terrible Mountain," where you'll arrive at the Weston Priory.

6.7 miles

You’ll walk dirt roads passing rural residences, community parks, and the village of Weston. Throughout your travels, you’ll have the chance to visit the Weston Priory (a scenic Benedictine Monastery), a cemetery from the 1800s, and, maybe best of all, Weston village. In this quintessential Vermont village, you can enjoy browsing an art gallery, a Christmas shop, the grounds of the Weston Playhouse, the Weston Country Store, and the hugely popular Vermont Country Store where you can sit down for a full meal at one of their two restaurants.

Enjoy a home-cooked 3-course dinner

Enjoy a typical Vermont country breakfast each morning prepared for you by our innkeepers.

In order to keep this walk manageable, you will be driven to a starting point about 10 minutes from COHO Inn & Motor Lodge.

Stagecoach Route to Inn Victoria – 11.8-mile route

A few miles outside the historic village of Grafton is where you will start your walk.  Meandering through vistas of the Green Mountains on this rural country road is a special experience; at one time this was the main route used by travelers between Chester Village and Grafton via stagecoach.  You will be delighted by the quiet, peaceful environment that at one time was the back settlement / farming community adjoining Chester.  At one point you will cross Popple Dungeon Road, its name derived from the large groves of Poplar trees that once grew here. They were very dense and close to the road, blocking out much of the light and giving the feel of being in a dungeon.  Your final leg of the journey, Dodge Road, will take you through the same route school children walked daily from the farm to their schoolhouse in Chester.  That schoolhouse remains today just as you cross the suspension bridge over the Williams River into Chester.

Plan your travels accordingly. You’ll arrive at your car in the afternoon after walking 10-12 miles or so. If you haven’t yet booked a fifth night directly with an inn, we recommend doing so. If you have already made a reservation for an additional night, be sure to work directly with that inn to confirm the details.