There’s more to the season than brilliant fall colors. Read on!

A fall foliage view from the Bennington Battle Monument.
Fall view from the Bennington Battle Monument. All photos by Phil Holland

September 29, 2022

“Intense Interest” in the Walloomsac Inn

If you’ve ever driven through Old Bennington, you may have noticed a grand, gaunt, gray structure half-hidden in foliage at the corner of Monument Avenue and West Road, opposite the cemetery and the Old First Church.

Chances are, your curiosity was aroused.

In recent years, two elderly sisters lived there privately; both died last year. The third sister and her son are considering what to do with the historic structure known most recently as the Walloomsac Inn.

The Inn grew from the tavern built by Elijah Dewey in the new settlement of Bennington in 1771. It was where Jefferson and Madison put up on their tour of the new state of Vermont in 1791. It’s where you yourself may have stayed prior to the Inn’s closing in 1984.

The Walloomsac Inn in Bennington, Vermont.
The Wallomsac Inn

You can’t go inside the building, but some of its precious contents will be on display at the Bennington Museum beginning October 1 (there’s a pre-show opening the afternoon before). The Museum and the family have worked together to satisfy what the Bennington Banner has called “intense interest” in the Inn on the part of the general public.

If you want to take a closer look at the outside of the Inn, there is ample parking by the cemetery. You’ll notice that the overgrown vegetation has been trimmed back, the first step in what all hope will be the preservation of one of Bennington’s most iconic buildings.

The Apple Barn is Back

Outside sign at the Apple Barn in Bennington, Vermont.
The Apple Barn

Step inside and it will envelop you: the heady aroma of fresh donuts, apples, coffee, hot cider and old wood. You have arrived in Vermont.

If you’re a fall-only visitor, you may not have known that the Apple Barn, a popular roadside institution reopened in September after a summer of downtime as it changed hands.

The best news is that Sarah Albright, the new owner and a long-time local resident, hasn’t changed the Barn’s cider-donut recipe, the one that makes a light, fragrant, dunkable donut. The pies will seem familiar to the faithful, too, as well as the welcoming atmosphere.

The apples still come from beautiful Southern Vermont Orchards, only a few miles away up Carpenter Hill Road, and tourists still carry boxes of donuts off with them like so much treasure.

Interior of the Apple Barn in Bennington, Vermont.
Apple Barn offerings

Sarah has introduced a few new items herself: delectable apple fritters, chocolate-covered “turtles”, and a unique ice cream flavor made by Manchester’s Wilcox Dairy: Apple Barn Apple Cider Donut Vanilla.

Try the buttery, locally produced Hoppy Valley cheese right off the wheel. Local maple syrup (from the Armstrong family), local honey (from the Fahey’s), and other Vermont products are also on offer.

No wonder the Apple Barn is often visitors’ first stop in the state if they’re coming up Route 7 from the Berkshires; for them, Vermont Begins Here.

Sarah Albright with a slice of buttery pub cheese at the Apple Barn in Bennington, Vermont.
New Owner Sarah Albright with a slice of buttery pub cheese.

Save the Date: 2022 Harvest Festival

Harvest Festival poster for Bennington, Vermont.

On October 15, the Better Bennington Corporation invites you to indulge in “all the cozy sweater-weather activities you can imagine!” at its annual Harvest Festival. Whatever the weather, imagine music, vendors, and good seasonal things to eat and drink.

Island Flavor: Something different, something delicious

Island Flavor sign in Bennington, Vermont.
Welcome to Island Flavor

The island in question is Jamaica, and the food at the newly opened Main Street takeout-only eatery is the real thing: jerked chicken, plantains, and curried goat, among other authentic Jamaican specialties.

The owners of Island Flavor in front of their storefront in Bennington, Vermont.
The owners of Island Flavor, Anique and Joan Gilpin, with Joan’s fiance, Kenny

The mother-daughter team of Anique and Joan Gilpin, native Jamaicans who came to Bennington several years ago, run the operation, as well as a clothes and housewares shop next door.

Island Flavor is open six days a week (closed on Saturday) from 11 a.m. to 9 p.m. 

All About Bennington in Three Easy Panels

An attractively designed three-panel display highlighting Bennington’s history and its cultural and recreational assets has been installed behind the Hotel Putnam complex at the center of town, adjacent to a municipal parking area.

What is the face of Peter Dinklage (better known as Tyrion from Game of Thrones) doing there? Take a look and find out.

Phil Holland of Pownal writes a monthly post for Vermont Begins Here.