Travel on your own. Share the adventure.

Experience the Vermont Inn to Inn Walking Tour on a special departure designed for solo women travelers. Enjoy scenic walks through Southern Vermont, welcoming inns, delicious meals, and the opportunity to connect with other women along the way - without needing to bring a travel companion.

Over four nights, you’ll stay at four distinctive inns, exploring the countryside between each stop. We provide walking maps, luggage transfers, and tour guidance; leaving you free to enjoy the journey.

This tour is being offered on three dates, all starting at the Inn Victoria.

May 16th, 2027 / July 11, 2027 / August 29, 2027

Choose the room option that feels right for you:

• Shared room with separate beds: Share a twin room with another woman joining the tour. You’ll each have your own bed - a great option if you’re open to meeting someone new and sharing the experience.

• Your own private room: Enjoy a room entirely to yourself, with space to unwind and recharge after a day of walking. You’ll still have opportunities to connect with fellow travelers along the route and over meals.

Both options include four nights of accommodations, four breakfasts, four dinners, luggage transfers, walking maps, and tour support.

Whether you’re craving a little independence, new connections, or simply a few days outdoors, these departures offer a welcoming way to explore Vermont on your own terms.

Plan to arrive at Inn Victoria between 3:00 and 4:00 PM to settle into your room before the tour begins. Dinner is served promptly at 6:00 PM, providing the perfect opportunity to meet your fellow walkers and get acquainted with the group.

Following dinner, your innkeeper will lead your first Walk Talk—an informative orientation covering the week's itinerary, what to expect on your first day of walking, trail logistics, luggage transfers, and helpful tips to ensure you're prepared for the adventure ahead.

Enjoy a three course home-cooked meal

Each morning, you'll enjoy a typical Vermont country breakfast, prepared fresh by our innkeepers.

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.

Each morning, you'll enjoy a typical Vermont country breakfast, prepared fresh 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.

Each morning, you'll enjoy a typical Vermont country breakfast, prepared fresh by our innkeepers.

Take a short shuttle ride from Ludlow over "Terrible Mountain" and on to the Weston Priory to begin your walk.

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.

Experience the charm of COHO Inn & Motor Lodge, set against the backdrop of the beautiful Green Mountains. Enjoy cozy accommodations with a touch of retro-style decor and easy access to local attractions.

Each morning, you'll enjoy a typical Vermont country breakfast, prepared fresh by our innkeepers.

Enjoy a scenic shuttle, pass Magic Mountain and arrive near the idyllic village of Grafton to begin your final walk.

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 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.