Southern Vermont

From left: The Dorset Inn, Manchester Designer Outlets.

ago and stayed, in various locations, until he died in 1963. He bought an old stone farmhouse in South Shaftsbury just north of Bennington in 1920, and he wrote “Stopping By Woods on a Snowy Evening” there one summer morning in 1922. Frost’s house has been turned into the Robert Frost Stone House Museum, now under the auspices of Bennington College. You can visit his gravesite, too, behind the beautiful Old First Church in Old Bennington.

You can’t go up inside the Bennington Battle Monument during the winter months, but the 306-foot limestone obelisk, which commemorates a pivotal Patriot victory of the Revolutionary War, dominates the landscape in all seasons from its perch in Old Bennington. The nearby Bennington Museum devotes a room of its rich and eclectic collections to the Battle; an adjacent gallery is home to the largest exhibit of paintings by Grandma Moses (Anna Maria Robertson) in the world. If you bring children, be sure to take them into the transplanted schoolhouse where the artist learned her ABCs in the 1860s; it’s meant to be played in as well as learned from.

In the 19th century Bennington emerged as an important and innovative industrial center, a heritage it still proudly continues. Timber frames, airplane components, snowshoes, craft beer, jewelry, and stoneware from famous Bennington Potters are among the many products manufactured here. The Potters’ funky-elegant retail store is located right next to where its wares are made. The Potters’ physical store is closed at present, but the online shop is open. You can still shop in person for fine Vermont jewelry and crafts at Hawkins House on North Street in Bennington.

While a major downtown redevelopment is nearing completion, a new brewpub, Farm Road Brewing, now occupies one of the corners of the town’s central crossroads. The Blue Benn Diner has reopened under new owners. This classic 1940s railcar diner is great for breakfast and lunch and has a menu for all tastes. For lunch, Sunday brunch, or dinner, the Mt. Anthony Country Club offers locally sourced seasonal dishes and beautiful views.

The Vermont Arts Exchange has resumed its public events schedule, as has Bennington College, although the college’s online calendar remains robust. Oldcastle Theater Company, now in its own building near the center of town, has not announced any winter productions. If you like covered bridges, Bennington has three of them. Scoot right through them all (one car at a time) on the way to North Bennington, if you’re willing to meander across the Walloomsac River three times.

North Bennington was writer Shirley Jackson’s home for the latter half of her life, but the natives insist that the village was not the setting for “The Lottery” (Raising Demons and Life Among the Savages, her hilarious accounts of child-rearing in the 1950s, are another matter). The fanciful Park-McCullough Historic Governor’s Mansion in North Bennington was built in 1865 with money made in California and Panama by an attorney who had grown up in the modest town of Woodford, just east of Bennington. The trails in the adjacent McCullough Woods are a popular spot for walking. The mansion’s grounds are open daily; “The Big House” is open for self-guided tours Fridays, Saturdays, and Sundays.

The Appalachian Trail crosses through Woodford five miles east of Bennington on its way up the spine of the Greens. The Vermont section, known as the Long Trail, was the inspiration for the AT, in fact. Robert Frost and his family were among the first to hike it when it opened in 1922.

Arlington, just above Shaftsbury on Route 7A, is home to the woodsy West Mountain Inn, the stately Arlington Inn, and the Rockwell’s Retreat; the painter Norman Rockwell lived and worked in a house and studio near a covered bridge over the Battenkill before moving south to Stockbridge in the ’50s.

Once a summer retreat, Manchester is now a four-season leisure and shopping destination. Hotels, inns, and B&Bs abound, led by establishments like the Mt. Equinox Resort and The Inn at Manchester. Some, like the Wilburton Inn and the Barnstead Inn, also host fun musical events. A range of restaurants caters to visitors and locals alike, from the tavernstyle Firefly (choice of locals) to tonier establishments like the Copper Grouse inside the Taconic Hotel. Robert Todd Lincoln’s historic home, Hildene, perched on an escarpment, overlooks the Valley of Vermont; don’t miss the deeply moving President Lincoln exhibit upstairs or the fully restored Pullman car, queen of the railroading era and a stop on Vermont’s African American Heritage Trail, a short walk from the main dwelling.

And then there is shopping. Charles F. Orvis got it started in 1856 when he opened a store dedicated to fly-fishing and accessories for the great outdoors. The flagship store is still there, and it has the distinction of being the oldest still-operating mail order business in America. Manchester Designer Outlets are home to many leading clothing brands, whose easy-to-get-to stores make bargain hunting a pleasure. For books and gifts, there’s the well-stocked Northshire Bookstore in the center of town, which, in non-COVID times, hosts frequent readings by leading writers. There are also stores for cooks, wine-lovers, artlovers, antique-hunters, and for sports enthusiasts of every stripe.

In nearby Dorset, in the fateful summer of 1776, the idea of Vermont as an independent republic was born in Cephas Kent’s tavern. In today’s Dorset, the aura of the 18th century lingers. The tavern is no more, but the splendid Dorset Inn has dominated the town green since 1796. If you’re “from away” and are thinking of buying and running a Vermont country store like the wonderful 200-year-old Dorset Union Store (and bakery) on the green, read Ellen Stimson’s Mud Season first; she bought and ran that very store and lived to write (and laugh) about it.

Baldwin Hill, Egremont

The Taconics rise like a wall along the Massachusetts–New York border. Half a dozen roads connect the two states where the range lets down its guard, but otherwise only hikers and black bears pass over a ridgeline that runs from Mount Everett in the south to Berlin Mountain in Petersburg, N.Y., in the north. Seven Berkshire towns lie along the border: they are (south to north) Mt. Washington, Egremont, Alford, West Stockbridge (see page 16), Richmond, Hancock, and Williamstown (see page 32). With the exception of Williamstown, they all play second fiddle to the larger towns immediately east of them— and that is one reason they have something special to offer the visitor, the second-homeowner, and of course their roughly 13,000 year-round residents.