Here Are The 14 Oldest Towns In Kentucky... And They're Loaded With History

The Bluegrass State entered in the Union of the United States on June 1, 1792 as the 15^th state to join. It took a little bit longer for folks to get settled in. Once word caught on, people started to group together and the first and oldest towns were born. Each one built from the ground up and gathering tales told over the decades. Many of these amazing communities still stand, though the architecture has taken a turn. Some old structures in the historic towns of Kentucky have remained well preserved.

Here are 14 of the most historic towns in Kentucky:

Don O'Brien

The Poage family came to Ashland in 1786 from the Shenandoah Valley and built a small homestead on the Ohio River’s south bank deemed Poage’s Landing. As people traveled the Ohio, some stopped and made their homes in the general area, which slowly built up into the town of Ashland, named after Henry Clay’s estate in 1856. Part of Ashland's growth was due to the pig iron and coal industries.

j Stephen Conn

This frontier town was actually founded in 1786 by a gent named Philip Buckner. It was named after Augusta County Virginia and continued evolving into the beautiful community it is today. Augusta, unlike many settlement towns, was home to not a one room schoolhouse, but instead held five separate schools. There was even a college deemed the Augusta College from 1887 until 1896.

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JP McCoy

This community began in 1779 as a 2,000-acre land grant from the state of Virginia to Leven Powell. The area was huddled in between Middlesburg on the east creek bank, and Gandertown on the west. Mr. Powell created the name Bloomfield from Bloomer, the maiden name of his wife, and Merrifield, his daughter’s marital name. Today, Bloomfield is a beautiful part of our agricultural community.

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J Stephen Conn

Cadiz is mentioned in "History of Trigg County" circa 1884, via Henry Perrin, though the origin of the name is not elaborated on. It has been said that one of the surveyors was a Spaniard and Cadiz was his home town in Spain. He suggested it as a name and it stuck. Local lore has maintained that as reason enough to have a town with a Spanish name. Cadiz is also home to a very popular Country Ham festival.

Civil War

Eddyville was the seat of Lyon County in 1798, Livingston in 1799 and Caldwell in 1809. This gives it the distinction of holding 3 county seats simultaneously for a short period of time. It is also home to the renowned Eddyville Penitentiary, which has been completed and gazing over the Lake Barkley area since 1890. It is not the most comforting shadow looming over the lake, but it does hold a lot of history.

J Stephen Conn

Harrodsburg is Kentucky's first permanent English settlement west of the Allegheny Mountains established in 1774. The town will celebrate its 250th birthday in 2024. Due to attacks from locals, it wasn’t truly settled till 1775, and then it was still hostile territory. It was one of three settlements in the Bluegrass State during the American Revolutionary War. It was also lovingly referred to as Oldtown back in the late 1700s and is home of the "Mother Town" monument.

J Stephen Conn

This community was once known as Jacksonville, named after General Andrew Jackson. However, John Quincy Adams and Henry Clay conspired against him establishing an anti-Jacksonian party which pushed a name change. A local landowner donated more than 100 acres to help form the community, so they deemed the new name Jamestown, after James Wooldridge, and it stuck.

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The Iroquois Nation once ruled this are but European settlers started homesteads in the late 1700s. A frontiersmen made the first small settlement in 1775, but the American Revolution brought a swift end. Simon Kenton returned in 1784 after the war and started building again, this time a frontier fort and trading post. In 1787 the settlement was incorporated into Maysville and with less than 10,000 residents, it is still considered a relatively small town.

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J Stephen Conn

Today Monticello is known as the self proclaimed houseboat capital of the world, which is appropriate given the close proximity to Lake Cumberland. Those who visit this hub of water enthusiasts in modern times might be shocked to learn in once was a grand community of less than 40 people. One of the original cabins belonging to John Smith still sits in Downtown Monticello as part of the historic preservation plan.

Josue Goge

This thriving community began on land purchased from a grant. The name Newport given to the town had nothing to do with location. Instead, it was named after the Commander of the very first ship to reach Jamestown in Virginia during 1607, Christopher Newport. Though Newport was recognized fully in 1834, it was actually established as a community in 1795.

USDA

A politician named Richard Menefee and a local foundry owner named Thomas Dye Owings donated the land for Owingsville. Lore has it that Owings built his home quickest, gaining the honor of having his name as the towns. General John Bell Hood, of the Civil War, was born in this quiet little place.

Rob Holland

This town, though not well known, was actually designed by the renowned William Clark, of Lewis and Clark. The community has a great local for trade along the river and came with a reputation. It was named Paducah due to the lore affiliated with Chief Paduke and his trip of Paducahs, though not of the Chickasaw tribes. Instead, the name came from the Comanches, who were once known as the Padoucas.

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Remains of the original Native occupants date back in this area for over 15,000 years. The area was initially known as Bullitt’s Lick because of the large salt deposits found by Captain Thomas Bullitt in 1773. Though you wouldn’t know it today, Shepherdsville was home to the first commercial salt works in the state. The renowned didn’t last as Kanawha River competition in Virginia shut things down. The town grew around the original Mill. In 1936 there was a mineral spring spa that opened up called Paroquet Springs. Today, the name still exists but instead of a spa it houses business offices and restaurants. The small town charm is quickly being overtaken by big city technologies and business.

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This charming town is close to Fort Boonesborough, which actually predates the American Revolution. It is home to civil war sites, historic churches, old cemeteries and the downtown district is on the National Register of Historic Places. Winchester might best be known for the creation of a favorite Kentuckian treat, Beer Cheese in the 1940s. There is even an annual festival celebrating the creation and consumption of this gooey, tasty treat that goes well on sandwiches, pretzels, and other dipping favorites.

These are just a few of the historic towns in Kentucky, as we were among the first 15 to join the nation. These towns are in the company of the renowned towns of Bardstown, Lexington and Louisville along with many others. What historic towns do you think should have made the list?