Past Times: Stories from the Sheldon's Past

The Oldest House in Middlebury

By Jan Albers

This article appeared in the Addison Independent in April 2010 and is published here with permission.

It would be easy to miss the small, white house squeezed in between the National Bank’s drive-through branch and the Middlebury fire station on Seymour Street. You can tell from its stark, Federal lines that the center hall structure was built early, but not everyone knows that 7 Seymour Street is probably the oldest remaining house in the village of Middlebury.

Dudley House

The first Gamaliel Painter house, also known as ‘Dudley House’ for Simeon Dudley, the builder and original owner

Middlebury was home to a few settlers before the American Revolution, but most were forced to flee as British General John Burgoyne’s troops terrorized the Champlain Valley in 1777. When that conflict was resolved in the settlers’ favor, people began drifting into the valley of the Otter Creek. In the decade before Vermont statehood in 1791, over three hundred people had come to live in the Middlebury area, though most were staking their claims south of where the village sits today. When settler Jabez Rogers arrived, he wrote that the few buildings clustered near Middlebury Falls were, “Chiefly log houses and almost wholly temporary buildings, built with small expense.” That first Middlebury more closely resembled Plimoth Plantation than the colonial village we might imagine.

The average settler family’s dream house was not a log cabin, but a proper clapboard home like the one they had left behind in Massachusetts or Connecticut. So in 1787, Simeon Dudley hatched a plan to erect the first frame home in the village. Dudley already had a reputation as a competent builder. He had been hired to build Stillman Foot’s mill on the west side of the Creek in 1785. His work was good enough that, in 1787, the ambitious Gamaliel Painter poached him from his rival, hiring Dudley to put up a mill for him on the east side of the falls.

Dudley was a handy man to have on the frontier, for he was a good builder and tough enough to live rough until the town got established. Historian H.P. Smith wrote that when he was putting up the Foot mill, he lived in “a shanty…in which he spent two years without chimney or cellar.” When he jumped the Creek to work for Painter, he built a similar rude structure for himself, but “this was burned before it was finished.”

Perhaps the romance of frontier life was wearing thin by this time, because Dudley decided to build himself a proper clapboard house like people had back in civilization. The dwelling he started hammering together was not then located where it is today. The builder had a prime lot on the hill over the Creek, just above and slightly south of the site of the later Civil War monument. Here he built himself a tidy one-story house with a chimney on each end. He moved in that summer.

The year 1787 was a momentous one for the new village, because at about this time, Gamaliel Painter was deciding that Middlebury Falls was a better village site than the one he had originally identified further south. When a new survey showed that his stake was actually in Salisbury rather than Middlebury, he swapped the land for prime falls-side real estate and positioned himself to lay out a new village.

When Painter got sight of Dudley’s modern clapboard house, he determined that he had to have it for his family. (Picture a rustic version of Henry VIII seeing Cardinal Wolsey’s magnificent Hampton Court Palace and saying, “I’ll have this house for myself, thank you very much. Build yourself another.”) He ordered a second story added for his larger family. From that time on, Painter would always aim to live in the best house in town.

By the fall of 1787, the Painter family was ready to move from the farm in Salisbury to the little house, where they hoped to create more of a village life for themselves. Middlebury historian Samuel Swift described the ‘town,” as it was then. “The whole region was covered with a thick and gloomy forest of hemlock and pine, except small spaces about the mills and small tenements, which had been erected.”

Here, on their first Christmas in the frame house, the Painters hosted what has come down as the most famous holiday party in early Middlebury. They invited all the settlers of the hamlet—the Foots, the Goodriches, Colonel Sumner, the Severances, the Chipmans, the Mungers, Seth Storrs and more–to warm their new home. They ate, drank and visited, enjoying a brief respite from the isolation of frontier life.

One of the guests was Cornwall farmer Samuel Bartholomew, nicknamed the ‘Apple Man,’ well-known for promoting the apples in his new orchard. He also had a knack for versifying on every appropriate occasion. He commemorated this festive gathering by writing a little poem:

This place called Middlebury Falls
Is like a castle without walls.
Surrounded ‘tis by hemlock trees
Which shut out all its enemies.
The pow-wow now on Christmas day,
Which must resembled Indian play,
I think will never be forgotten
Till all the hemlock trees are rotten.

Simeon Dudley came out of the house deal in good shape. Painter had land at his disposal, and the first one-acre lot went to the builder, Simeon Dudley, who took possession of it on September 10, 1788. Painter meant for Dudley to build a much-needed tavern there, on the plot where the Middlebury Inn now stands. Dudley abandoned the plan and sold it to Samuel Mattocks, who built the first tavern on the site in 1794. Dudley seems to have left Middlebury before that time. The Censuses of 1790 and 1800 found him living in New Haven with his wife and five children.

The little clapboard house was only a temporary stopping point for the Painter family. Gamaliel’s crew was building them an impressive new mansion on the crest of the hill behind the little house. This beautiful Federal-style mansion (now home to the Addison County Chamber of Commerce) was topped by a monitor, with windows overlooking Painter’s bustling little hamlet.

The Painters’ new home was finished in 1802. In that year, Painter sold their first little house to Robert Brigham, seemingly with the proviso that he would move it to a new site. In this era, it was common for whole buildings to be relocated, and many of Middlebury’s first dwellings were eventually moved.

How did they move a building in the early 19th century? The process was easier than it is today (though in the past few years Middlebury College has given us ready evidence that it can still be done). There were no wires for electricity, telephone or cable and no plumbing hookups to disentangle. No one needed to get a permit and the traffic was not an impediment.

Rough outbuildings were often disassembled and then reassembled like a puzzle on the new site. But houses with interior plastering were usually taken off their foundations and moved in one piece to a new foundation. Screwjacks were used to lift the building and then horses pulled it onto a large, flat sled made for the purpose. Houses were almost always moved in the winter, when it was easiest to slide them along on the snow and ice. In warmer weather, they could be moved by resting the sills on a series of rollers and then pulling with a team of horses. As the house moved forward, workmen grabbed the back rollers and ran them up to the front so they could proceed.

Employing one of these methods, it was a short, straight downhill hop from the top of South Pleasant Street to the new site on Seymour Street, where it settled onto its new foundation. The little house stayed in the hands of the Brigham family until Henry Sheldon bought it as a rental property in 1874. After two years, he sold it to John Stewart. When the marble company built the Marble Works, they bought the building, probably to house some of their workers. The photograph shows it in that era, largely devoid of paint, with the wheel house towers and marble sheds in the background.

The oldest house continues its useful life today as a suite of offices for small businesses. The next time you drive through the ATM next door, take a moment to admire its clean lines and remember the settlers who came together there to celebrate surviving and thriving in the hemlock woods of Middlebury in the winter of 1787.

This article appears with permission of the Addison Independent.