Primary Menu

Walking Tours

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.

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 Walk:

11.25 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 Pettigrew Inn

Built in 1829, the elegant building on Pleasant Street in Ludlow Village has been offering comfortable guest lodging for over 65 years.

Renamed as The Pettigrew Inn and revitalized with new ownership in July 2017, The Pettigrew Inn will be a welcome stop at the end of your scenic walk.  Refresh yourself in your luxurious guest room and then relax with a book and a beer or glass of wine in the sun-room, or on one of the many outdoor rocking chairs around the property.  Or if there is still a little spring left in your step, head down the block to explore the galleries and shops within Ludlow Village.

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 Pettigrew 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 snack on free samples or 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:

Popple Dungeon Creek to Inn Victoria – 10.8 mile route

Today’s walk will take you along the length of Popple Dungeon, a dirt road that travels through the old original farm settlements. The road gets its name 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. The walk will initially take you by a hill-top championship golf course owned by Okemo Mountain Resorts called Tater Hill Golf. The walk will continue through the old farm settlements showcasing Popple Dungeon Creek, which meanders across the road at least a dozen times before you arrive at Inn Victoria.

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.

Spring & Summer Rates

May 15 to August 31, 2022

  • $1,798 per couple / double occupancy
  • $1,498 single occupancy
  • $2,698 triple occupancy in the same room

Fall Rates**

September 1  — October 31, 2022

  • $2,298 per couple / double occupancy
  • $2,298 single occupancy
  • $3,398 triple occupancy in the same room

**NOTE:  September and October (All tours start on Sundays only.)

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

There is something about Vermont that just warms the heart.  We loved every second of our time in VT.

Sandy & Jim
Danvers, MA

We just returned from our walking tour.  If we could have, we would have gone for a second lap.  Each of the four inns had its own character, but each offered the same wonderful hospitality and top-notched accommodations and meals.  We met friendly, interesting fellow walkers who were “birds-of-a-feather”…people who live to travel and travel to live.  Each day of walking offered beautiful scenery and well thought out routes.  Thanks to these wonderful inn-keepers who made this a truly memorable experience!


Ahhhhh…the peaceful quiet of it all.  We especially enjoyed looking up at the stars each night.  Light pollution is so minimal, we could see forever!

Patty-Ann & Dave