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    Middletown is one of the most historic locations within Jefferson County, originally chartered in 1797. Along with having a long and charming past on its resume, it also served as a portal for the journey for most spectators into Valhalla for the Ryder Cup. Its residents are proud of the deep heritage, beautiful scenery and neighborhood feel. Mayor J Byron Chapman takes us inside this quaint little city that may be in the middle, but most certainly stands alone!

    1. What is your history with the city?

    I moved to Middletown in 1969 after serving in Vietnam. I have lived in Middletown with my wife, Freda and my 2 children who also live in Middletown and are raising their families here as well. With my family, we own and operate our businesses in Middletown. I was a Middletown Commissioner for 10 years and have been the Mayor now for 6 years.

    2. Describe Middletown in one word?

    "Home" or "Friendly"

    3. Something about Middletown that no one knows?

    I would have to say our history. Not many people know the depth of history Middletown has to offer. We were the home of one of the state Governors, We were the carriage stop between Louisville and Frankfort, and we have a large historical district with amazing history in each home. An unpleasant fact about Middletown but funny, the largest tape worm on record, was treated in Middletown in the first doctor's office in Middletown in the late 1800!!!

    4. Tell us how Middletown got its name?

    Middletown was the stopping point between Louisville and Frankfort. Many people would stay in our Inn, which is now operated as a museum by the Civic Club. We have historic signs that designate these wonderful landmarks such as the Taverns, stores, etc. You can still see the Mile Stone markers used by travelers. This is why we are called "Middle" town.

    5. Middletown is best known for?

    Southern Hospitality! Our quaint restaurants, unique shops and friendly "hometown" feel make us special. But, we also have a fast growing corp. and commercial business area which the City Officials work to make the two mesh together. We hold monthly concerts in the park for our residents and visitors and seasonal activities like Light Up Middletown and our Festival.

    6. Most visitors to Valhalla took a little journey through Middletown as part of the trip out to the course. Tell us a little bit about that experience?

    Middletown was honored to play a large part in the Ryder Cup and to be the "gateway" for visitors to come through and see our wonderful town.

    7. What is in store for Middletown in terms of development and growth?

    Middletown strives to give back to its residents and businesses. We look forward to continuing street and landscape projects, improving and creating more parks and green spaces. We look forward to new and exciting events and activities for our families and residents.

    Business Snapshot:

    Best Cup of Coffee- I have to say I like our locally owned Dairy Queen. They are so involved in Middletown and supporting our families and schools. They also always have a friendly face behind the counter!

    Best Happy Hour: I love to got to Rumors because I can meet my kids and grandkids there, see friends I know, and have a great dinner! It's a fun place!

    Best home cooked meal: We have so many great restaurants and cafes in Middletown- Grapevine Pantry, Cottage Cafe, Mazonni's, Mark's Feed Store and Pig City for BBQ, and of course, my favorite Tiffany Cellar Cafe (I own that one with my family!)

    Best Place to Escape- I love our Middletown Park. I often take walks there with my family. With the City Hall located there, our gazebo, town clock and newly renovated streets, it is truly relaxing with the hometown feel.

    Best shopping- Where do I start!! We have so many stores and great shops. We have a business association, Middletown Operated Businesses, or the MOB, what works to make these little shops and stores known! The MOB holds quarterly Limousine Hops, playing off the trolley hops, which pull together the historic stores along Main St. and the more commercialized stores on Shelbyville Rd. They call it "Shopping in Style"! The next hop is Nov. 8 and that will be the Holiday Open House for the businesses. You can go to their website,, to see a list of the stores and businesses. Thank you for your interest in Middletown. I love this city and everyone that lives here or visits us, leaves here with the same love for our town

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    Holly Freeland's picture

    About Holly Freeland

    I graduated from Western Kentucky University (GO Tops!) with an English and Journalism degree. I spend my time playing soccer, watching UK basketball, stalking David Beckham and laughing at Chelsea Handler.

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