In 1856, James Woods, a local builder, completed the larger of our two houses. He then sold the property to Thomas Jefferson Wertenbaker, the son of Thomas Jefferson's close friend and the University of Virginia's first librarian, William Wertenbaker.

The house changed hands in 1882. Another distinguished family, the Valentines, moved in. Mr. Valentine was a prominent businessman with interests in a bank, the cable car company and the woolen mills here is Charlottesville. At this time the main building was the only building located on the block. The photograph located in the rooms is the house as it was in 1903 when the Valentine family occupied it.

Most of the original furnishings are in the Valentine Museum in Richmond, Virginia. Mrs. Irene Valentine, whose husband Vinton was born in room 9 (the portrait of the young boy in room 9 is Vinton, age 3, painted by his older sister in 1888), the family later resided on Park Street here in Charlottesville. Once the Valentine’s sold the property it became a girl’s finishing school. The houses were bought in 1984 from 'Blind Jennie' Donaldson, who ran the property as a boarding house and lived in what is now our second, smaller building. Brendan and Jenny Clancy own the Inn. They became involved with the Inn in 1991 and have owned the business for fifteen years.