The Benjamin Head House

Myths & Legends Surround 200-Year-Old Middletown Landmark

Writers / Steve Wiser & Jack Koppel

At the northeast corner of Main Street and Harrison Avenue in the Middletown Historic District sits a quaint building which, if its stone walls could talk, would reveal more than 200 years of the fascinating past of this eastern Jefferson County community.

Before delving into the distinctive background of this charming structure, the myths surrounding it must first be dispelled.

A former historic marker once stood at this location that contained several inaccuracies. While now removed, this plaque remains in cyberspace and continues to generate misunderstanding.

Accurate documentation of historic sites and individuals has greatly improved over the past 30-plus years due to online sources such as genealogy and research databases. Prior to the advent of these vetted computer-accessed resources, stories of people and places typically were based on family recollections conveyed over decades via verbal and handwritten accounts, which were not the most reliable for verifiable facts.

Such are the tales once associated with this humble edifice, now known as the Benjamin Head House (11601 Main St., Middletown, Kentucky). The former plaque described Benjamin Head as a “Revolutionary War veteran captain.” Yet, verified genealogical records show the Benjamin Head who built this house was born in 1782 — one year before the Revolutionary War ended. However, there was another Captain Benjamin Head elsewhere in Kentucky who did serve in the Revolutionary War. The confusion between the two Benjamin Heads evidently stems from their shared death year of 1837.

The second misinformation on the plaque noted that the “fact” was based on a “legend.” But this “legend” was inscribed and therefore became accepted as truth. The claim was that the Head House “once changed hands as the result of a poker game.” This assertion was even repeated in a 2012 Courier Journal article.

However, descendants of John Hansbrough, who obtained the house from Head in 1821, deny this ever happened, citing Hansbrough’s strict religious beliefs, which forbade gambling.

Another myth claimed treasure was hidden inside during the Civil War to protect it from thieves. No loot was ever found.

Lastly, even digital resources can be flawed. The website FindAGrave.com lists Benjamin Head’s birth year as 1780, but his headstone clearly states 1782. The discrepancy stemmed from a misreading of his obituary, which noted he died “in his 56th year.” That phrase means he was between 55 and 56 years old at his death.

With the myths addressed, here is the verified history of the landmark. Benjamin Head was born in January 1782 to Hadley and Mildred Head in Virginia, according to Ancestry.com. He settled in Middletown around 1804 and by 1815 was a town trustee. (Middletown was chartered in 1797 and named because it was the midpoint between Shelbyville and Louisville on the old turnpike road, now Shelbyville Road.)

Head partnered with Basil Nicholas Hobbs (1786-1837) and Benjamin Lawrence in the Head, Hobbs & Lawrence General Store. Head traveled by horseback to Philadelphia and Baltimore to purchase supplies, while Hobbs kept the books.

In 1808, Head married Harriot Hobbs (1787-1824), sister of his business partner Basil. Their father, Nicholas Hobbs (1747-1793), was the grandfather of Edward Dorsey Hobbs, who later helped establish the Anchorage community.

As for Head’s other partner, Benjamin Lawrence, his history remains unclear. He is often confused with another Benjamin Lawrence who fought in the Revolutionary War.

According to Middletown historian Edith Wood, construction of the Head House began in 1813—not 1812, as other sources and the former plaque state. Head completed it in 1815, but sold it just six years later to John Hansbrough. The reason for the quick sale remains unknown.

William Chambers purchased it after Hansbrough but abandoned it during the Civil War. The next long-term occupants were William H. and Catherine Abel, married in 1858, who lived there until 1877 when Dr. Silas O. Witherbee bought the home. Four of the Abels’ six children were born in the house. The Witherbee family owned it into the 1960s. They were related to the Wetherbys of Middletown, including Kentucky Gov. Lawrence Wetherby. In 1974, Chris Matthews purchased and restored the house.

Byron and Freda Chapman bought the home in 1996. Byron became Middletown mayor in 2001 and remains in office. Over the years, the Head House has been both a residence and the site of businesses and a restaurant.

Capstone Realty purchased it in 2020 and conducted an extensive renovation for its headquarters, including re-supporting structural beams, refinishing the original ash wood floors, and other improvements. The Head House is now on the National Register of Historic Places.

After selling the house, Benjamin Head bought a farm several miles west that was later owned by his great-grandson Robert Chester Tway, who developed a dairy there. In 1923, Tway built a large home designed by the noted firm of Nevin, Morgan & Wischmeyer. Today, that house at 10235 Timberwood Circle in the Plainview neighborhood is owned by the City of Jeffersontown and serves as a civic center.

Following the death of his first wife, Harriot, Head married Margaret Nora Brengman (1805-1891) in 1824. Known as Nora, she was the daughter of Martin Brengman and the aunt of Catherine R. White, who with her husband, James Goslee, built “The Anchorage” estate in the mid-1800s. Their property gave its name to the Anchorage community, connecting Head in a roundabout way not only to Middletown but also to the development of Plainview and Anchorage.

After Head’s death in 1837, Nora remarried Henry L. Garr. Head is buried in Middletown Cemetery, but his exact gravesite is unknown. His headstone, once damaged, is now displayed at the Middletown Museum at 11700 Main St.

Basil N. Hobbs is buried in Hobbs Cemetery in Anchorage. The gravesites of Harriot Hobbs Head, Margaret Nora Garr, and Benjamin Lawrence are unknown.

Steve Wiser, FAIA, is a local historian, author and architect. Jack Koppel is a local historian and docent at Middletown Museum.