This unassuming little home, located on the north side of Van Dorn Avenue, is actually one of the oldest surviving structures in Holly Springs. This is “Old Traveler”, a home with a whimsical but accurate name. Though it has been added onto and renovated many times over nearly two centuries, Old Traveler started out as a dogtrot double log cabin, built in 1836. It was built just two years after the Treaty of Pontotoc, between the Federal government and the Chickasaw Indians, opened up the land in north Mississippi to white settlers.
Old Traveler, also known as the Woodruff-Fennell Place, was built by Aaron Woodruff (1799-1859), an early settler to Holly Springs who owned a local gunsmith shop next door to this house. The original location for the house was at the northeast corner of College Avenue and Spring Street, just south of the original “holly springs”. Today the Baptist Church Office is located on this spot. Old Traveler saw the settlement of Holly Springs slowly grow around it, until the town was officially founded in 1836, and the center of activity shifted south to the town square. The log cabin was originally used as a barbershop and public bath.
In 1860, Aaron Woodruff’s widow Sarah Woodruff (1806-1893) sold the house to John B. Hill, who owned the house from 1860 until 1866, when he sold it to Susan B. Wooten. Wooten owned the house from 1866 until 1870, when it was sold to Robert Roth, who lived here until 1882. In 1882, the house was bought by Martha T. Fennell (1834-1918). After Fennell’s death in 1918, the house was bought by Jessie V. Hogan (1896-1971). The Hogans lived here until 1952, when the house was sold to Charles N. Dean Jr. (1927-1983). Dean made extensive renovations to the house, and in 1960 he moved it across town to its present location, on Van Dorn Avenue.
After Dean’s death in 1983, his widow Phoebe Moss Dean Copeland sold the house in 1988 to William H. Thomas. In 1994, Thomas sold the house to Walker Thomas Hurdle, who sold the house one year later to Michael and Sherry Cowen, who continue to own the house today.
Old Traveler is a one-and-a-half story clapboard residence, built over the original log cabin of 1835. During the renovations of 1960 three gable-front dormers were added and the original porch was removed.
Hill Country History 
It’s older than our central log cabin! I know there must be others, but this is the first one I’ve read about.
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Diane, where do you live?
Another “clapboard-over-log” (the technical architectural term) house is McCarroll Place, across the street from us on Van Dorn as well.
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Nit-picking, but this house was not on the corner but in the middle of the block. On corner of Randolph was a big white Victorian house with beautiful porch, in my day turned into two apartments. Bill Boone’s family lived upstsirs, and the Barlows lived downstairs. What a tragedy that it was torn down to build that monstrosity of metal.
On the east corner was the Victorian cottage (seen in photo) where Bonnie Davis and family lived. It was torn down about the same time as everything else was cleared.
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Thanks Betty! I’m about to post a blog post on that Victorian house (the Myers House, which replaced the old Franklin Female College).
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Error in my post. I have no sense of direction! The Davis cottage was west of Old Traveler! 😁
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