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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. Or You may choose to enter the village of Cavendish and explore beyond the route a bit to discover the wondrous Cavendish Gorge.

Spring & Summer Rates

May 15 to September 11, 2019

  • $1498 per couple, Double Occupancy
  • $1298 Single Occupancy

Fall Rates**

Sept 15 to Oct 31, 2019

  • $1898 per couple, Double Occupancy
  • $1698 Single Occupancy

**NOTE: October (Midweek only: Sunday – Thursday)

Cancellation policy

There is a 14-day window just prior to the actual tour start date which gives the inns time to rebook the tour space should you need to cancel.  We understand that there may be a need to cancel a tour for health or emergency needs at home; for this reason, we have developed a cancellation policy that can guide you.

  • Notices of cancellation must be received no later than 14 days prior to scheduled start of the tour. Cancellation must be accomplished via the telephone.  1-833-INN-2-INN (466-2466)
  • Prior to 14 days, we will retain 50% of the deposit.
  • There are no refunds within the 14-day window, nor during the tour.
  • We suggest purchasing travel insurance, much like you would for any other major vacation. This link is one example of several insurers that offer travel insurance.  The cost is minimal, and the process is easy.   allianztravelinsurance.com

Rates apply to adults and children age 15 and older.

Children under 15 cannot be accommodated on tours.

Reservations

— 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

So enjoyed dipping our feet into the cool, clean, and clear waters of the various streams!

Ken & Darlene
Austin, TX

Oh God, I thought we’d lose some weight on this walk.  Not to be.  The food was way too incredible!  Thank you!

Jolene & Mike
Southern, CA