The early history of
Gaylordsville is closely connected to the Gaylord family, or Gaillard,
as the family was known in France. In 1630 William Gaylord arrived
in Nantucket harbor on the ship "Mary and John", which
had sailed from Plymouth, England. He later settled in East Windsor,
Connecticut. His great-grandson, Ensign William Gaylord, moved
to Woodbury in 1706 and married Joanna, the daughter of Captain
John Minor. Joanna's sister, Grace, married Samuel Grant, and
was an ancestor of President Grant.
In 1712, the Gaylord couple came to New Milford, Connecticut,
which had been settled only five years previously. Their house
stood on the corner of Main and Elm Streets. For a time he kept
a tavern there in addition to doing his regular work as a surveyor.
He did a lot of surveying for the State, laying out town boundary
lines, and it was, no doubt, on one of these surveying trips that
he became impressed with the large areas of level land several
miles north of the New Milford village, just north of the straits
on the Housatonic River. He began taking title to parcels of it,
and soon owned a large part of the valley. To insure the good
will of the Indians living in the area, he also bought it from
them, giving, according to legend, a horse, a mule, and a two-wheeled
cart.
In 1722, a highway was laid out 'by marked trees' north from New
Milford to the brook called Whemiseck. The blazed trail ran through
Squash Hallow, past the straits, and over Cedar Hill. Mr. Gaylord
was probably the surveyor who laid out this road, and probably
put it over Cedar Hill so it would not cut into the level areas
that were to become his fields.
In 1725, Mr. Gaylord travelled this trail from New Milford and
built a log cabin west of the Housatonic just north of the straits.
He lived in this cabin three years while he was clearing land,
cutting timbers, and building his frame house, which he built
in 1728. The following year his oldest son, Aaron, built a house
about a quarter of a mile south of his father's, and on the west
side of the valley.
During this time the Gaylord family became good friends with their
Indian neighbors, teaching them better methods of agriculture,
and dickering with them for furs they could use. The family consisted
of Mr. and Mrs. Gaylord, Aaron, Joanna, Ruth, Benjamin, and Mary.
Benjamin remained at his father's home, and eventually took over
the homestead. He married Tryal Morehouse on October 23, 1745.
William Gaylord died October 25, 1743, at the age of 73. His grave,
and that of Mrs. Gaylord were the first ones in a cemetery that
had been laid out about half a mile south of the Gaylord home.