Feeling minuscule, I stand at the foot of the Bennington Battle Monument, trying to glimpse the top of this 306-foot-high blue-grey magnesian limestone obelisk. Its impressive height and the choice of stones perfectly commemorate the pivotal Revolutionary War battle on August 16, 1777. During the battle, Brigadier General John Stark and his army defeated two detachments of British General John Burgoyne. And so I begin my exploration of Bennington and the covered bridges of Vermont.

Note: Featured image above courtesy Vermont Department of Tourism

This 306-foot-high stone obelisk celebrates the Battle of Bennington during the American Revolutionary War. Photo by Renate Strub

All in all, Vermont is a jewel state, small but precious – Pearl S. Buck

Looking through narrow vertical slots on a high-up interior observation deck, I am breathless as a sweeping view of Vermont — and Massachusetts and New York beyond — opens up before my eyes. I look down on the streets and houses below. Then my eyes wander across a vast expanse of fields and hills covered by dense vegetation until they come to rest on the gentle curves and slopes of mountains on the horizon.

In the 1600s, the French explorer Samuel de Champlain called the Green Mountains Verd Mont, meaning Green Mountain, which became Vermont. Its nickname Green Mountain State comes from the mountain range extending 250 miles from north to south through the center of the state.

The Bennington Battle Monument is located in the Old Bennington Village, part of Bennington town. Designated a National Historic District in 1984, every house in the village is recorded on the National Register of Historic Places.

Bennington

A quintessential small Vermont town (population around 15,000), Bennington is rich in history and culture. I start my discovery tour by immersing myself in the world’s most extensive collection of art and personal objects of Grandma Moses at the Bennington Museum.

Next, I go down memory lane to my childhood and delight in the dollhouses and toys at the 1850s Dollhouse and Toy Museum of Vermont.

To me, literature is an essential part of Bennington when I think about Robert Frost and his magnificent writings. His residence is the place to go to delve into memories of when you read his books in your teens. Frost wrote many of his masterpieces in what is now the Robert Frost Stone House Museum; his gravesite is nearby in the Old First Church Cemetery.

Robert Frost Stone House Museum. Photo courtesy of Bennington College

In Vermont, restaurants, farmers’ markets, farm stands are never far away. Nor are some delightful old covered bridges.

Covered Bridges of Vermont

Crossing streams and rivers, one can almost hear the clatter of horse hooves elegantly cantering across the covered bridges of Vermont more than a hundred years ago.

Steeped in history, these simple yet elegant structures amplify the picturesque Vermont landscape, especially those painted in a vivid red contrasting with the countless shades of green of the forests and fields in summer. They blend with the renowned autumnal extravaganza in fall as the trees dress in myriad tones of yellow, gold, and red.

Interior West Arlington Bridge. Photo by Renate Strub

The roof’s primary purpose was to preserve the structural timbers from the damaging effects of the weather. Without it, the supporting trusses would have deteriorated rapidly at a time when treated wood wasn’t available. The high windows provide natural light and let people see oncoming traffic.

The architects might not have thought of this; still, the walls and roof gave livestock a sense of security as they crossed the bridges over rushing rivers, calming the animals and preventing stampedes.

According to the Official Vermont Government Website, a Federal Highway Administration survey determined that Vermont ranks third in the nation with the most covered bridges. There are a stunning 100, dating from 1820 to 1982. Ninety are listed in the National Register of Historic Places.

Paper Mill Bridge

My first stop is at the Paper Mill Bridge, a 125-ft.-long red bridge with a white trim lattice truss that crosses the Walloomsac River on Murphy Road. Due to deterioration, the 1889 bridge had to be removed, and this replica was built in 2000.

Paper Mill Bridge. Photo by Renate Strub

During the Industrial Revolution, abundant water from the river and now dormant dams made this an excellent location for various industries, including a paper mill, hence the bridge’s name.

Parking on the north side just a few feet from the entrance to the bridge, I am surprised to see various posters describing the history of this place. Peeking inside the bridge, I admire the inner structure and the lattice windows. Do be careful and watch for oncoming traffic.

Poster showing the history of the Paper Mill Bridge. Photo by Renate Strub

Silk Road Bridge

Now my curiosity is piqued, and I want to see more bridges. Just a few minutes from the Paper Mill Bridge, I find the white-trimmed red lattice truss Silk Road Bridge that also crosses the Walloomsac River. I stand by the side of the bridge for the longest time, mesmerized by the serene and peaceful scenery as the river flowed around a bend, only to disappear below the bridge. Leaves on a nearby tree rustle in a gentle breeze and a profusion of orange flowers sway back and forth.

Silk Road Bridge. Photo by Renate Strub

Eighty-eight feet long, this bridge resembles the Paper Mill Bridge. Rumors are that father and son Benjamin Sears and Charles F. Sears built these bridges. Constructed in 1840, the Silk Road Bridge was added to the National Register of Historic Places in 1973 and restored in 1991.

West Arlington Covered Bridge

Even though a bit out of town, I have to visit the West Arlington Covered Bridge. One of Vermont’s oldest, it is said to be the most photographed and painted bridge in Vermont. Crossing green fields and winding around tree-covered hills makes the drive feel short.

Built in 1852 and renovated various times, with a green roof and five windows on each side, this red bridge is 80 feet long and 17.5 feet wide. Its interior discloses the beautiful latticework and stunning intricate structure of interconnecting triangles that give this truss bridge its strength.

West Arlington Bridge crossing the Batten Kill River. Photo by Renate Strub

The picturesque surroundings make this bridge especially attractive; the wide shallow Batten Kill River invites me to take a few steps down a footpath and stroll on its peaceful banks. In late spring and summer, one might encounter some anglers fishing for trout — reportedly the best in the state — or an artist painting the bridge.

Batten Kill River, popular with anglers and artists. Photo by Renate Strub

Rockwell’s Retreat in Vermont

Walking back to my car by the Chapel of the Green, the 1792 colonial Rockwell’s Retreat across the road catches my attention. I was told I could book Norman Rockwell’s bedroom overlooking the chapel and the bridge. Norman Rockwell’s bedroom? The painter and illustrator best known for his depictions of small-town life? One of my favorite artists? I must be dreaming.

As Sue Harter of Rockwell’s Retreat told me: “Norman Rockwell moved from New York to Arlington in 1939. His studio burned in the spring of 1943, and he moved up the road to our site on the West Arlington green overlooking the covered bridge. He lived in our inn from 1943 to 1953 when he moved to Stockbridge, MA. We have restored his studio back to its roots as it was when he was painting in it.”

In rural Vermont, history and culture are never far apart. Covered bridges, an intrinsic part of Vermont, bring the past to your present. They let you visualize bygone eras, enjoy the present, and dream about a future filled with promise.

Check out Wander’s other fabulous articles about New England and get great ideas for more road trips.