Cynthiana, KY

Some small towns in Kentucky are smaller that others. With our many travels I’ve come to notice that the small towns that are the county seats tend to be larger than the rest. I’ve also noticed that these towns typically have that traditional “courthouse square” layout.

Cynthiana, KY breaks the mold on both of those typical characteristics.

Cynthiana is the county seat of Harrison County. It has an incredibly beautiful courthouse, but one who visits will not notice a small town courthouse square. Cynthiana’s downtown sprawls out beyond a square. Still laid out in the square format, you’ll find streets running parallel and perpendicular in all four directions . Cynthiana’s downtown is larger than other county seat towns. It just might be the largest small town I have seen, and while I know small towns are not just their historic downtown areas, when I think about the size, that’s what comes to mind.

Fall Decor on the Courthouse Lawn / Personal Photo

Cynthiana is doing an amazing job of revitalizing their historic downtown area. There are bookstores, boutiques, coffee shops, restaurants, and more filling the store fronts of this historic district. It is a large small town keeping its quaint small town feel. You truly must visit to experience it for yourself.

Downtown Cynthiana merchants have inherited a remarkable cultural resource – well designed and high style architecture from America’s elegant Federal period, from the exuberant Victorian era and from the boom years on the twentieth century. Meanwhile, revitalization efforts in the downtown area continue to keep the town as the hub of the community.

Cynthiana, KY Chamber

Creating Harrison County

As I discussed in a Kentucky History Trivia post, Kentucky began with nine counties and over time worked its way up to one hundred twenty! Needless to say, every county after the first nine were created from the first nine. So, in 1793, just one year after the birth of Kentucky, when Harrison County was formed, it took its land from portions of Bourbon and Scott Counties.

Colonel Benjamin Harrison

The county was named after Colonel Benjamin Harrison, who is said to have settled in the area in 1776. Harrison became a Colonel during the Revolutionary War, serving in Pennsylvania. He later made his way down the Ohio River to Bourbon County, Kentucky arriving at Ruddle’s Station, a pioneer settlement.

Ruddell’s Station was a pioneer settlement on the South Fork of the Licking River south of what is now Cynthiana in Harrison county on the trail from McClelland’s Station to Lower Blue Licks. It was settled in 1775 by John Hinkston and several families and further fortified by Simon Kenton and others in 1776. Hinkston’s Station was briefly abandoned and then occupied and enlarged by Issac Ruddell and his family in 1779 seeking protection from Indian raids. British troops and Indians attacked Ruddell’s Station in 1780, killing about twenty and marching the rest to Detroit as prisoners. The Ruddells were released a few years later and returned to their original home, which became the town of Ruddells Mills in Bourbon county, a few miles south of Ruddell’s Station.

Kentucky Atlas

He quickly became involved in politics and was one of several early settlers that pushed for state independence from Virginia. He represented Bourbon County in the early Kentucky Conventions of 1787 and 1788, he was appointed to choose the location of Bourbon County’s Courthouse, he attended the 1792 Constitutional Convention in Danville, signed Kentucky’s Constitution, and was elected to the Kentucky Legislature in 1793.

Being so involved with the early creation of our state, it is no wonder the county was named after him! Just be careful and do not confuse him with the many other Benjamin Harrisons of the time. To learn more about Kentucky’s Colonel Benjamin Harrison, click here.

Historical Marker / Personal Photo

Creating Cynthiana

Chartered as the county seat of Harrison County on December 10, 1793 and built on the land of early settler Robert Harrison, Cynthiana was named for Harrison’s daughters Cynthia and Anna.

Cynthiana Main Street

Robert Harrison donated his land to establish the town in 1793. According to the Kentucky DAR website, Robert, a blacksmith, donated “one hundred and fifty acres of land lying opposite the mouth of Gray’s Run for the site of a new town.” Shortly after donating his land to the town, Robert moved his young family to Ohio and later to Indiana, where he died between 1825-1828.

While Benjamin and Robert shared the same last name and were in the same area at the same time, my research shows no relationship between the two men.

Civil War History

On June 11–12, 1864 the Civil War Battle of Cynthiana was fought near Kellar Bridge. On the first day, Confederate General John Hunt Morgan and his 1,200 Kentucky cavalrymen captured the town, making prisoners of its Union garrison and the entire 171st Ohio Infantry Regiment. Despite being low on ammunition, Morgan chose to stay and fight the enemy forces he knew were on their way. Union General Stephen G. Burbridge and his 2,400 cavalry and mounted infantry attacked him the next morning, driving the outnumbered Confederates from the town and freeing the prisoners.

Cynthiana, Kentucky Chamber

Our Visit

The first thing that caught my attention was the architecture! Everywhere you turn there is a beautiful building to admire. Many historic churches still stand and the downtown area cannot be missed. It is listed as a historic district in the National Register of Historic Places.

Several outstanding examples of Federal-style architecture have survived from the community’s earliest years, and there are an exceptional number of mid-19th century buildings with cast iron storefronts. Cynthiana has the second-largest collection of such extant storefronts in Kentucky.  

Advisory Council on Historic Preservation

We started our visit with a coffee from the Main Cup. I had seen a post on Facebook that listed many businesses in town that were providing Fall-themed drinks, dishes, and desserts. My daughter is a huge fan of coffee and fall. The Main Cup had a Fall-themed coffee so we headed straight there to check it out! We ordered two different seasonal drinks and both were amazing. I only wish I remember what they were called!

After our drinks, we headed down the downtown streets and wandered in and out of many shops, bookstores, and boutiques. We fell in love with each place we visited; The Next Chapter Bookstore, Inspired Designs Boutique, and Molly B’s just to name a few. From there, we walked a few blocks to Leono’s Pizza for a late lunch after receiving a recommendation from a boutique shop owner.

Wrapping up lunch, we jumped in the car for the second leg of our adventure. I had done my research before heading for Cynthiana and I knew there was a nature preserve near-by where we could hike along the banks of the Licking River. Setting my Waze app on my phone for Quiet Trails State Nature Preserve, we pulled out of the historic district and into the rolling hills of Harrison County.

Now, I’ll be honest, we drove for what seemed like FOREVER! We quickly went from an urban area to the rural hills of Kentucky and while the views were beautiful, we lost our cell signals and didn’t see another car in sight for way too long.

We finally arrived at the area marked as the nature preserve, but the road and the views didn’t change. We drove for awhile longer along the narrow, winding road hoping to find the hiking trails and the Licking River. As you see by my photos above, there was no sign of a river anywhere! We also never came across marked trails of any kind. We clearly were not in the correct section of the 165-acre preserve and we were running out of time.

With no signal, no signs, little time, and a daughter who now needed a restroom break, I carefully turned the car around in the middle of the narrow road. I felt confident there would be on issues with oncoming traffic! We retraced our steps and headed for the nearest restroom and finally for home.


The Historic District of Downtown Cynthiana is worth the trip if you enjoy quaint boutiques in historic buildings. There is a sweets shop there that I am eager to visit on another visit. I don’t recommend combining the nature preserve with it. I would opt for one or the other. I’m sure the nature preserve is great, if you find the hiking trails! I recommend more research of the exact location before you go. The views were beautiful, and the colors breathtaking, so I would recommend the visit in the Fall.

I truly loved this trip. I believe Cynthiana just might be my favorite small town of all those we have visited, so you know that says a lot!

Publishing this in February, I know you are probably not going to get out and explore right now. Mark your calendar for Spring when the sun warms the air and the flowers begin to bloom. More than likely by then, you’ll be ready for walks along the historic streets of Cynthiana!

Happy Travels!

2 thoughts on “Cynthiana, KY

  1. Thank you for writing about my beautiful home town. My father’s men’s clothing store was right across the street from that beautiful Court House! I am sorry there were no markers for the trails and sanctuary, hopefully they will correct that. Love your writing, keep it up and where you going next?!?!?!?

  2. My Harrison Co roots go deep. My Great Grandfather name was John Morgan Cromwell. John was Mayor of Cynthiana for many years in the 20th century he was born in 1862 and was head teller at the bank. He also wrote a column in the cynthiana Democrat Called Cromwell Comments is my for many years. Many years ago the historical Society put a book together with his column it is a great look at the Bluegrass and Harrison Co. it can be found at the Cynthiana Museum. I could go on and on about many other Cromwell men but maybe later.

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