1805, shortly after he moved to what is now Penn Yan, Sheppard added to
the land he held at the head of Main Street. Four years earlier, he had
come up from Pennsylvania, married a girl from the infant settlement's first
family, and built himself a double log house on ten acres his new wife's
cousin gave him. Now he bought an additional four acres on the other side
of the wide and muddy street that as yet had no name.
a year later he sold off half this land to Abner Pierce, a newcomer from
Massachusetts who was a blacksmith; he was the first in the village, and
the first in this part of the village that within a few years became the
industrial heart of the settlement. The same day he bought his two-acre
parcel, Pierce sold off the lot at the corner for the village's first store.
months later, Sheppard sold the other half of the parcel to John O'Brien,
father and grandfather of later John O'Briens who became commercial stalwarts
in Penn Yan. The first O'Brien built a house that evoked some vivid memories
later on because it had a picket fence around it.
never abandoned his interest in this parcel, however. He later reacquired
much of it, and in fact built his "yellow house" there, not too
far from the tavern stand that followed the old store. In the early 1820s
he built "Mechanics' Hall," a five-story commercial extravaganza
that contained a warren of stores and shops, and the hall of the Vernon
Lodge, the area's first Masonic organization. Soon after Mechanics' Hall
burned in 1826, Sheppard built his third and final home on the site, the
stone mansion that still stands at 342 Main Street, near the south end of
Abner Pierce's half of the original parcel.