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

Golden Stage Inn is the newest member of the Vermont Inn to Inn Walking Tours, but they’re hardly new at 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:

6.7 miles

In order to keep this walk manageable, you will be driven to a starting point less than 15 minutes from Golden Stage 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 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:

Flamestead Road to Old Town Farm Inn – 9.3 mile Route

Today’s walk takes you through the Chester Green past small bookstores, antique shops, the old rail Depot, past the old grist mill, and on the road to country fields and vistas. Once on Flamestead road, you will walk a few miles on a very quiet asphalt road that takes you up along the ridgeline of a hill, which allows for incredible views of the valley below. Horses, wild turkeys, deer, and spectacular views are the charm of this area. The sky is bigger than big, and you’ll wish you could live here! Eventually you will walk onto dirt roads most of the distance and ranging through fields, ponds, very old cemeteries, and more.

Old Town Farm Inn

Imagine a farm stay bed and breakfast owned by a world-class Japanese Chef, in Vermont. Old Town Farm Inn, a twenty-room, 1861 Classic Revival farmhouse, has been renovated into a seven-guestroom country inn. The grounds feature a stocked spring-fed pond and the farm atmosphere to go with it.

Enjoy a welcome beyond compare with Michiko’s hospitality; afternoon fruits and juices to replenish your body after the day’s walk are plentiful. Later in the evening enjoy a traditional Japanese meal that you will remember forever. Relax in the parlor or by the fish pond….either way, you’ll love the hospitality, food, and atmosphere of a real farm country inn.

Brief Description of the Walk:

7.9 miles +/-

If nature and trees are what you’re looking for on this trip, this walk may be your perfect match. Most of the walk is up and down the hilly winding roads of a state forest. As you approach the village of Cavendish, the Black River forms cavernous waterfalls for you to enjoy in the ams gorges. Walk through Cavendish village in which you can stop at the small general store for a sandwich or a drink and also visit the site of the historic Phineas Gage accident and its monument. (Google him for more info!) You may choose to conclude your day’s walk with a swim in the in-ground pool at Golden Stage Inn.

Spring & Summer Rates

May 15 to August 31, 2018

  • $1498 per couple, Double Occupancy
  • $1290 Single Occupancy

Fall Rates**

Sept 1 to Oct 28, 2017

  • $1798 per couple, Double Occupancy
  • $1590 Single Occupancy

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

Cancellation policy

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 in the event you do have a need to cancel.  The reason for the 14-day window noted below is to give time for the inns to rebook the tour space should you need to cancel.

  • Notices of cancellation must be received no later than 14 days prior to scheduled start of the tour.
  • A 25% service charge will be applied.
  • There are no refunds within the 14-day window, nor during the tour.

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 802-875-4288

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

Sandy & Jim
Danvers, MA

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

Each year our group of 8 friends travels to one location and does something fun together;  to date, the Vermont Inn to Inn Walk has been the best!  We came together from all parts of the country and fell in love with Vermont!

Dayton, OH