This year marked the Jennings family’s 14th year of celebrating Halloween together, with a special theme honoring America’s 250th birthday! The family consists of 11 members spanning three generations: parents David and Judy Jennings; their oldest daughter and her husband, Sara and Chris Charles, and their daughters, Allison and Olivia Charles; their next-oldest daughter and her husband, Mary and Derek Adams, and their children, Chet and Molly Adams; and their youngest daughter, Ellen Grace Jennings.
The three generations range in age from family patriarch David Jennings, 71, to the youngest grandchild, Molly Adams, just 4 years old. Although the family has always enjoyed dressing up, the tradition of coordinating costumes around a group theme began in 2013. The roots of the tradition, however, go back much further — to two very special women who helped make Halloween memorable for generations: the children’s grandmothers.
Both grandmothers loved Halloween, dressing up, handing out candy and preparing a big pot of chili. Their maternal grandmother, affectionately known as Mamaw, transformed her carport in Paintsville with black tarps, disco lights and music. Children from nearby hollows would gather to enjoy her homemade chili and receive candy. The experience offered a glimpse of a simpler, country-style Halloween, where children truly walked from house to house through the hollers.
Their paternal grandmother, known as Grandmommy, lived in Beattyville, allowing the family to spend many more Halloweens with her. She loved preparing chili and handing out candy at Gourley Heights. Those evenings were filled with visits from neighbors and community families, costumes and trick-or-treating from house to house in what felt like a sweet, storybook neighborhood.
Both grandmothers have since passed away, but the traditions and memories they created continue to live on.
In their honor, the family gathers each year to vote on a Halloween theme, coordinate costumes, enjoy chili and hand out candy during Trick-or-Treat on Main in support of their church, St. Thomas. Afterward, the children in the family get to trick-or-treat at Gourley Heights, giving the next generation an opportunity to experience the same special memories their parents and grandparents cherish.
Over the years, the community has shown the family tremendous support, not only for their annual Halloween themes but in countless other ways. As a way of expressing gratitude and giving something back, the family launched Costumes for a Cause in 2025.
The concept is simple: For every like received on the family’s annual Halloween Reveal post, one dollar is donated to a local charity or organization of their choosing, up to a predetermined maximum donation amount. The family keeps its theme a secret until shortly before Halloween, making the annual reveal even more special. The initiative was created as a way to give back to a community that has given the family so much. This year’s donations will benefit Lee County Veterans and Passionately Pink.
The family says the community means so much to them, and they are humbled by the continued support. Their hope is to carry on the tradition for as long as they are blessed to do so. More than an annual Halloween celebration, the tradition represents three generations coming together to honor their roots, remember loved ones, support their community and create lasting memories for the next generation.
It is a celebration of family, tradition and the special community that has helped make it all possible.
Info via Ellen Grace Jennings
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