West Dummerston Covered Bridge // 1872

Oh covered bridges, one of the many symbols of New England that always give me joy when I see them! This beauty was constructed in 1872 to span the West River in Dummerston, Vermont and is the longest that is wholly within the State of Vermont. The bridge was designed by Caleb B. Lamson, a master carpenter and the bridge is the only known bridge built by Lamson that survives. Vermont is significant for covered bridges as about one hundred bridges still stand in the state, which is probably the greatest concentration by area of covered bridges in the nation. A reason we have to thank Vermont for this is purely population. With more people living in the state, transportation demands change, and these bridges are often replaced with modern steel structures. Keep doing you Vermont!

Kipling Carriage House // c.1893

Located at the Naulakha Estate in Dummerston, Vermont, the Kipling Carriage House has long served as a companion to the larger Shingled home. This charming building originally stored author Rudyard Kipling’s carriage and an apartment space for his coachman. The quaint structure sits atop a high stone foundation and retains much of its original detailing, and inside, the structure oozes charm! After Rudyard Kipling sold the estate, the next family converted the structure to a servant’s quarters. In 1992, the British-based Landmark Trust acquired Naulakha as its first American building, later creating the Landmark Trust USA who maintain the property to this day. Like Naulakha, the Kipling Carriage House is available for short-term rentals, which helps the Landmark Trust USA maintain and restore these historic buildings.

I was fortunate enough to be able to spend a couple nights at the Kipling Carriage House and the experience is something I will hold with me for the rest of my life. The wood-lined walls, historic windows, cozy furniture, and fireplace, make you feel so at home, and sweeping views of the Connecticut River Valley add to the splendor. There is something so great about “unplugging” from screens and reading one of Kipling’s books by the fireplace in one of his properties!

Sleepy Hollow Farm // c.1780

Without question, this property is the most photographed site in the tiny town of Pomfret, Vermont, if not the state. The property dates to the late 18th century when John and Samuel Doten moved to the newly settled town of Pomfret Vermont, overlooking the growing town of Woodstock in the valley below. The two brothers acquired vast farmland on the hills of Pomfret and each built farmhouses adjacent to eachother, with Samuel getting elevated land and John developing the land sunken off what is now known as Cloudland Road into this stunning property. Sleepy Hollow Farm remained in the Doten family for centuries until the 1950s, when the owners sold the property to move to Woodstock and work for Laurance Rockefeller, the famous philanthropist and conservationist, who later donated his Summer home in Woodstock to the National Park Service. The property sold numerous times in the late 20th century, and is presently owned by Aerosmith guitarist Joe Perry and his wife, Billie. They are clearly great stewards to the property’s rich history and various outbuildings, and must not care too much to have swarms of photographers at the end of their driveway year-round!