For the 50+ Traveler
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Walking tours are the perfect way to immerse yourself in the culture of a local community. You can enjoy a close-up experience of the food, the land, and the way of life along your journey.

The Vermont Inn-to-Inn Walking Tour is a series of four walks over four days, totaling 44 miles. The inn you are assigned to for your first night dictates the order of your walks. Each inn provides an afternoon snack, a home-cooked dinner, a hearty breakfast, a comfy bedroom, and baggage transportation to your next overnight accommodation. When you set off in the morning, they prepare you with a selection of deliciously nutritious snacks, water, and a set of detailed directions. You park your vehicle at the first inn and retrieve it when you complete the four-day loop back to the start.

There were three of us on this trip, ranging in age from 58 to 70. We knew we would be walking at a slow-to-moderate pace, but we were of the mindset that it wasn’t a race -- it was a journey. A journey to prove we were still capable of accomplishing such a task.

The Inn Victoria in Vermont.

Our first night was at the Inn Victoria in Chester. The town’s main street was quintessential small-town Vermont, with beautiful old Victorian homes and historic clapboard buildings housing specialty shops.

We were cheerfully greeted by the innkeeper, Penny Cote; her husband, Dan, was working on the roof. They have been innkeepers at the Inn Victoria for more than 11 years, and they were friendly and gracious throughout our short stay.

While sitting in the parlor enjoying our adventure, we admired the Victorian decor: Cushy seating, bookshelves bursting with interesting titles, antique lace curtains covering arched windows, Tiffany-style lamps, antique tables, and handmade quilts worked perfectly together to create a soft, inviting space.

Penny's teapot collection at the Inn Victoria.

As we sipped our chosen tea blend, we admired Penny’s extensive tea and teapot collection. She is a connoisseur of all things tea.

In the morning, we set off with directions in hand and snacks in our bag. As luck would have it, our first hike was 13 miles, and the forecast was hot and muggy. We began with a walk through the village, and as we turned out of town, we entered the Stone Village. Chester’s Scottish settlers showcased their masonry skills along this stretch of road with beautifully constructed homes.

As we left the village area, we headed straight up. Villages in Vermont tend to be located in valleys, and to get to the next village, we needed to navigate several large hills and valleys. We walked through the Proctor Piper State Forest for most of the day. Given that the temperature was 90+ degrees, we were happy for the shaded paths. About 3 hours into our woodland walk, a pickup truck pulled up; it was Dan checking to see if we were okay and in need of water. This wonderfully kind act was above and beyond our expectations, and we were grateful.

About halfway into our walk, we enjoyed our inn-provided snacks alongside Dean Brook. It was a refreshing break and gave us energy for the rest of the long walk. Heading uphill and downhill in the heat made the last mile arduous. We were overjoyed to finally arrive in Proctorsville.

The Golden Stage Inn Bed and Breakfast in Vermont.

The Golden Stage Inn, our accommodation for the night, was operated by Julie and Mike Wood, a midlife-career-change couple who purchased the inn in 2010.

Once we had rested on the wraparound porch with iced glasses of homemade ginger lemonade, Julie walked us to our rooms, where our bags were awaiting our arrival. The rest of the afternoon, we enjoyed a hefty cheese and cracker plate along with a bottle of chardonnay, a dip in the pool, and some relaxing time in the garden. Dinner was perfection, followed by freshly baked cookies chased down with more ginger lemonade from the community fridge. As you might have guessed, we all slept oh-so-soundly.

Breakfast was served at 8 a.m., and we were scheduled to hike 11 miles that day. Mother Nature had other ideas, however, with rain and thunderstorms expected in the early afternoon. We decided to hike 11 miles, but not the route through the forest. Julie provided us with maps of local hikes, and we spent 2 hours (5 miles) climbing hills and exploring the woodlands in Proctorsville. Late that morning, we hitched a ride with our luggage to our next accommodation in Ludlow.

Not wanting to skimp on our pedometer total, we headed out to explore Ludlow, a fairly large town by Vermont standards. At one end was the Okemo Mountain Resort, a popular ski resort; at the other end was a quaint village. We finished off our 6 additional miles just as the thunderclouds rolled in.

The Pettigrew Inn in Ludlow, which Courtenay Dundy has owned and managed since 2017, boasted spacious and well-appointed accommodations. We were delighted to find hummus and veggie plates waiting for us in our rooms. After 11 miles of dodging storm clouds, we thoroughly enjoyed our snacks and a bottle of pinot gris from our packed stash as we watched the skies open up and the rain pour down. Sleep came easy after the long walk, the gourmet dinner, and the soft, comfy beds.

The Priory barn in Vermont.

The third day’s walk required a short drive to get us to our starting point. Since this was a 6.7-mile day, we were in no rush. After a filling breakfast, we enjoyed the sunshine in The Pettigrew Inn’s beautifully manicured gardens. We were dropped off at Weston Priory, a Benedictine monastery. The priory grounds were lovely, offering panoramic views of the surrounding hillside. We enjoyed a slow, peaceful walk on the labyrinth, setting our intentions for the day.

This walk was a nice mix of backcountry roads and village sidewalks. We arrived at the town of Weston, where the village green was large and inviting, the perfect spot for a snack and a rest. The Vermont Country Store is a Weston landmark and worth a visit. It is stocked with toys you’ll remember from your childhood, copious amounts of candy, and a wide range of all things country. At Mildred’s Dairy Bar outside the country store, we enjoyed a Maple Creemee, a maple-flavored, soft-serve ice cream -- the perfect midday hiking treat! On the rest of the walk, we passed beautiful farms showcasing the Vermont countryside.

Weston, Vermont.

At the Colonial House Inn & Motel in Weston, the innkeeper, Kim Seymour, greeted us with fresh fruit and delicious cookies from her brother’s bakery. As we munched happily in the sunroom surrounded by casual Vermont country style, we felt completely at home. Kim and Jeff are the second generation to manage the inn, taking over from Kim’s family in 2002. The antique charm of the inn made us feel immediately comfortable and relaxed.

Our last day was supposed to feature a 10.8-mile hike, but again, the weather was threatening. We opted for a drop off 2.7 miles into the hike, avoiding a very steep hill. We were glad to have our rain gear, since it poured! The tree canopy helped to shield us from some of the rain, but we were happy to return to our starting place, the Inn Victoria. Our bags were lined up in the parlor, and Penny had the kettle on for tea.

We had booked an additional night at the Golden Stage Inn, thinking that we wouldn’t want to drive home after a long day. It was a good decision. Since dinner was not included this time, we stopped at Singleton’s General Store for provisions. They carry everything from really nice wine and fine cheeses to clothing and ammo. We purchased wine, cheese, bread, fruit, and meat for a buffet spread. Julie and Mike were kind enough to let us take over a large table in the dining room, where we enjoyed our meal, reminisced about our wonderful trip, and basked in the satisfaction of a job well done.

Beautiful views of the Vermont countryside.

The directions provided by the innkeepers for the walks were extremely detailed, some up to three pages long. At times, it resembled a scavenger hunt: “Walk 50 feet; you will see a brownish metal gate with colored ribbons. This gate may be locked, but you may pass around it.” You’ll need to keep track of where you are, lest you miss a turn and your 13-mile day ends up being a 15-mile day due to backtracking. Fortunately, we never got lost.

We were fairly well prepared in terms of gear. It was really a walk more than a hike. However, it can be extremely hilly, and I was happy I brought walking sticks for the three longer days. If you make the trip, you should consider bringing a good, sturdy pair of hiking shoes and lightweight rain gear.

We were happy we had upped our walking game before the trip. The preceding few months, we walked 6 miles twice a week and made a longer, more strenuous hike each weekend to prepare. I am happy to say that we are still walking 6 miles twice a week. Our walking group is growing, and we are in the midst of planning our next overnight hiking adventure. It’s not always pretty, but it is moving forward!

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