Self Guided Walking Tours

Self-Guided Walking Tours

Go on a memorable self-guided walking tour and discover the beauty and hospitality of Vermont at our partner country inns along the way. See descriptions of each inn and each day’s walk below, and see what delights might await you in Southern Vermont.

Spring & Summer Rates

May 13 to August 21, 2024

  • $1,898 single occupancy
  • $2,198 per couple / double occupancy
  • $3,297 triple occupancy in the same room

Fall Rates

August 30  — October 31, 2024

  • $2,798 single or double occupancy
  • $4,197 triple occupancy in the same room

2024 Tour Start Dates

13, 18, 24, 30

5, 11, 17, 23

7, 13, 19, 25, 31

6, 12, 18, 30

8, 15, 22, 29

6, 13, 20, 27

Golden Stage Inn

The Golden Stage Inn has a history of welcoming guests to the Okemo Valley. The building itself began its relationship with travelers as a 1788 stagecoach stop. Michael and Julie-Lynn Wood are proud to have participated in this tradition of hospitality since they moved in 2010 from Massachusetts to their Vermont inn.  Whether you relax by the in-ground pool in the summer or visit the sheep and chickens, you’re sure to love strolling the property at Golden Stage Inn. Maybe you’d prefer to head inside to unplug with a puzzle or book — or plug-in using the complimentary Wi-Fi. While snacking from the Bottomless Cookie Jar, you can chat with Julie about her beehives and the amazing world of the bees. Singleton’s General Store is an easy half-mile walk down the residential street. This is a great place to replenish your stores of beer, wine, local foods and Vermont-themed gifts.

Brief Description of the Self-Guided Walk:

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.

The Governor’s Inn

The Governor’s Inn was built in 1890 by Vermont Speaker of the House William Wallace Stickney for his wife Elisabeth. Mr. Stickney went on to become the governor of Vermont in the year 1900. Located on Main Street in Ludlow, it was turned into a B&B in the late 1970s and has welcomed guests for almost 50 years.

Your hosts Rosemarie ( Rosi ) and Holger Stoltze await your arrival after your long walk.

Relax in the parlor and marvel at the original woodwork and fireplaces, sit in one of the rocking chairs on the front porch watching everyday life go by, or retreat to your elegant, well-appointed  guestroom to rest up for the next day.

You can also visit the village of Ludlow with its stores and galleries.

Brief Description of the Walk:

6.7 miles

In order to keep this walk manageable, you will be driven to a starting point about 10 minutes from The Governor’s Inn. 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.

Colonial House Inn, Weston

The Colonial House Inn is just minutes from the historic and picturesque village of Weston, Vermont. A former Cape-styled farmhouse dating back to 1810, the inn is nestled in the foothills of the Green Mountain National Forest on Scenic Bi-Way Route 100. Home to the famous Vermont Country Store, Weston is a “must experience” for all who travel Vermont; and your walk will take you directly through the village. The 14-room inn offers comfortable guest rooms, a charming guest living room and dining room. Breakfast (“Vermont’s Favorite” per Yankee Travel Magazine) and dinner are delicious New England fare including home-baked breads and desserts from the family bakery, Grandma Miller’s.

Upon your arrival you may relax in the guest living room with afternoon refreshments and homemade cookies as a treat after your day’s walk. Sit outside for quiet, reflective time and enjoy the views of Stratton Mountain, meander around the perennial gardens or relax with a book or puzzle. While you are here, consider this your “home-away-from-home” with your hosts, Jeff, Kim and Alexis Seymour.

Brief Description of the Walk:

Stagecoach Route to Inn Victoria – 11.8 mile route

In order to keep this walk manageable, you will be driven to a starting point about 10 minutes from The Colonial House Inn.

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.

Inn Victoria

Inn Victoria is an award-winning romantic Chester, Vermont bed and breakfast of 1859. The building sits on the Green in the center of Chester Village, amid several restaurants, bookstores, and antique shops within walking distance of the inn. This elegantly appointed English-style Victorian is a centerpiece of the Chester Village architecture. The main street is like walking through a Norman Rockwell painting. Indeed, Chester village is granted the award for the prettiest painted village in VT and one of the top ten in New England.

After a full day of walking, relax in the grand parlor, or on the front porch. Enjoy the hot tub on the quiet back deck where you can gaze at brilliant stars, so bright that you can see constellations you’ve perhaps not seen in a long time. The bedrooms are elegantly appointed with antiques and luxury baths.

Brief Description of the 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.

Cancellation policy

We understand that some circumstances may arise causing a need to cancel, so we want to be upfront and clear regarding our policies. The orchestration of the tour is complicated and intensive, involving four inns and many logistics. To secure your reservation, we require a deposit of 50% of the cost of your tour.  Once this deposit is paid, half of your deposit is immediately non-refundable. Two weeks prior to your tour start date, the remaining 50% of your tour price is due. Once this second payment is made, all monies paid are fully non-refundable.

If you are concerned about this cancellation fee, we suggest purchasing travel insurance, much like one does for any other major vacation. This link is one example of several insurers that offer travel insurance:  We are not affiliated in any way with this or any of the travel insurance companies.

Rates apply to adults and children age 15 and older.

Children under 15 cannot be accommodated on tours.


— Ready to Explore at Your Own Pace? —

Call 833-INN-2-INN • (833) 466-2466

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