Some people, like Chris and Heather Dempsey, are like oak trees. They have long, deep roots. 

The couple has drawn from those roots to create a house and related buildings on Roy Webb Road in Jacksonville. Altogether, the setting is a confluence of everything important to them: family, friends, history, place, music, vocation, and avocation.

The Dempseys have shared these important aspects of their lives with various local groups, and they are making plans to share even more in the future. This Christmas, they plan to open their home up for tours to groups at a cost of $10 per person. Visitors will see holiday trees decorated to match the War Between the States theme prevalent throughout the Dempseys’ home and grounds, and guests will enjoy hot chocolate and snacks after the tour. 

The Dempseys, who are parents of five-year-old Ada and two-month-old Ruby, teach English at Pleasant Valley High School. Their lives are busy doing the things they like best, which includes performing throughout the nation in an award-winning band called Un-Reconstructed. (I’ll write about the band next week.) 

Recently, I toured the Dempsey estate, called Fiddlers Green. Chris conducted my tour, while Heather and her mother, Peggy McAlister, tended the children.  I walked through the house, which is seven years old but looks as if it were built in the 1800s. In fact, much of the building materials came from the Lockett-Gidley house in Jacksonville that was torn down just prior to 2005 when the Dempseys began planning their house. 

“Maj. Samuel H. Lockett was an important but mostly unknown Civil War hero,” said Chris. “Also, he was an international figure who traveled to the West Indies and became an architect, an artist, an entrepreneur, and a soldier educated at West Point. He was responsible for holding back Union forces in Vicksburg, Miss. There is a statue is his honor there.”

Chris pointed out pine floorboards, mantels, a staircase, woodwork, and many other features from the Lockett-Gidley house. Also, he told how he and Heather collected furnishings from their own ancestry and from throughout the Southeast to decorate their home. It is helpful that his father, Gary Dempsey, retired Personnel Director at Jacksonville State University, is a master wood craftsman.  He has taught Chris many skills, and the two have worked together on many projects, including building a massive walnut and glass bookcase in the study and restoring pieces of furniture. Each item seems to have a story, from the large painting of a Southern beauty above the fireplace in the study (it is a painting of Heather) to a copy of a painting by Lockett of the fiery Civil War battle in Vicksburg, to antique books, a rug owned by the aunt of Harper Lee, a cast-iron fireplace with an un-scorched, wooden hearth-board from the Lockette house, and others. All are meticulously featured in the house. 

Then there are the grounds, which include a southern Victorian garden with two large fountains and a rose bush that has been transplanted from one generation of Dempseys to the next for at least 150 years, a carriage house that serves as storage for lawn equipment, a re-assembled log cabin discovered within an old house on family property, and a modern “outhouse.” A general mercantile store is open for business but still under construction. In addition, an iconic red barn completes the setting from its place at the bottom of the hill on which the other dwellings sit. 

The couple has, for the past several years, attended Civil War re-enactments. Their participation led them to stage their own. For the past seven years, other Civil War enthusiasts have come to the Dempseys’ property and set up camp during the first week in May. Ladies dress in period costumes and gentlemen dress in soldiers’ uniforms and carry out duties reminiscent of the 1800s.

The amount of work is staggering that has gone into the Dempsey estate, which is dedicated to the preservation of Southern history. This busy couple and a large supportive family are the source of the work. 

“We always say our home was a labor of love,” said Heather. “All of our family played a part in its construction.  We love being able to share pieces of Jacksonville’s history with everyone! We feel truly blessed.”

 Visit, or call Chris and Heather at 256-435-6055 to learn how they can serve families and groups, including the upcoming Christmas tours. 

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