Historic Buildings in Maysville Kentucky

9 Oldest Founded Towns To Visit In Kentucky

Admitted to the Union in 1792, the “Bluegrass State” of Kentucky is indeed one of America’s most fascinating places to discover. Known for its beautiful geographic features and unique cultural identity, Kentucky is surely a land where splendid nature and fascinating history come together. This is no better reflected than in its towns, each with its own special story to tell. These oldest Kentucky towns are then not just great destinations for an authentic slice of America, but a welcoming places of intrigue for visitors of all ages.

Augusta

Houses along the Ohio River in Augusta, By Augustaky - Taken while on the Augusta Ferry., CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=23962575
Houses along the Ohio River in Augusta, By Augustaky - Taken while on the Augusta Ferry., CC BY-SA 3.0, File:Augustariverline.jpg - Wikimedia Commons

The town of Augusta was founded as a trading post way back in 1786 and today maintains a most humble population of just over 1,000 residents. Situated on the southern bank of the Ohio River, this charming community is a great place to discover genuine small town allure. And with the beauty of the River never far away visitors can enjoy plenty of activities on the water’s edge. Amongst the most popular is surely a ride on the beloved Augusta Ferry (in continuous operation since 1798), where a sense of time travel will certainly be felt. In addition touring many of the historic riverside homes brings with it plenty of contemplation and intrigue, ideal for the travelling family or solo adventurer alike.

Cadiz

The courthouse in Cadiz burned twice during the American Civil War. This courthouse was demolished in 2008 to make way for a new justice center that opened in October 2009.
The courthouse in Cadiz burned twice during the American Civil War. This courthouse was demolished in 2008 to make way for a new justice center that opened in October 2009.

The seat of Trigg County, the historic town of Cadiz was founded in the 1820s. Today the home of just over 2,700 residents this picturesque community remains a favorite for those looking for calming relaxation near the water. Situated along the Little River (a 57 mile tributary of the Cumberland River), visitors to Cadiz will surely love the splendid opportunities for such activities like kayaking, canoeing, and even shore line jogging.

In addition Cadiz’s historic charm will be sure to delight and its assortment of historic buildings bring passersby truly back in time. Visit such sites like the County Courthouse or the beautiful Victorian mansion, the Fairholme completed in 1890. And of course like many small towns, a great variety of cute stores and tasty local restaurants are always ready to welcome guests and offer a special helping of Kentucky pride.

Maysville

Historic Buildings in Maysville Kentucky
Historic Buildings in Maysville Kentucky

Formally incorporated in 1787, the town of Maysville is beautifully situated on a stretch of the Ohio River. A historically significant place, Maysville was amongst many things a stop on the Underground Railroad (the now famed network of passages for fugitive slaves), an important River port, and a prominent exporter of items like tobacco and bourbon well into the 20th century. And with such memorable landmarks like the Russell Theatre (1930) and the iconic Simon Kenton Bridge (1931), there is never a shortage of memorable panoramas to be seen in Maysville. Indeed this seat of Mason County offers visitors loads of historic intrigue and natural beauty that surely makes for a most special small town Kentucky experience.

Newport

1884 Campbell County Courthouse in Newport Kentucky with fall colors
1884 Campbell County Courthouse in Newport Kentucky with fall colors

One of two seats of Campbell County (alongside Alexandria), Newport was officially established in 1795. Named after the commander of the first ship to settle in the Jamestown Colony, the modern town is home to a population of just under 14,000 residents. Situated at the confluence of the Licking and Ohio Rivers, Newport also straddles the border with the State of Ohio and can be also considered a part of the Cincinnati Metropolitan Area. A hub of the Northern Kentucky region, visitors will find a beautiful place steeped in history but comfortably at pace with the present. Stop by the charming historic district, catch some Kentucky Bluegrass sounds, or simply stroll alongside the river’s edge, Newport is indeed a wonderful place to discover for visitors of all kinds.

Paducah

Historic buildings in Paducah, via Sabrina Janelle Gordon / Shutterstock.com
Historic buildings in Paducah, via Sabrina Janelle Gordon / Shutterstock.com

Paducah was first settled around the year 1821, and today this charming Kentucky town is home to just under 27,000 inhabitants. Seat of McCracken County, the town is located right where the Tennessee and Ohio Rivers meet and is part of the Jackson Purchase region of the State. The site of numerous historic points of interest, much of the downtown area of Paducah has been listed as National Historic Landmark where numerous 19th century and early 20th century edifices populate the area. In addition the town boasts a vibrant local arts scene, and beautiful wall mural installations can be found all around. And naturally with its vicinity to the water, opportunities for swimming and boating are always popular activities in this most charming of all Kentucky towns.

Winchester

Main Street in Winchester, By I, W.marsh, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=2267047
Main Street in Winchester, By I, W.marsh, CC BY-SA 3.0, File:Winchester, kentucky.jpg - Wikimedia Commons

With foundational roots dating back to 1792, nearly 20,00 people now call Winchester home. Seat of Clark County, this historic town is full of fascinating landmarks, Civil War sites of importance, historic churches, and a most intriguing downtown district listed on the National Register of Historic Places. Explore such places like the Clark County Courthouse (1855), the Old Providence Church (1793) and Oakwood Estate House (1820) amongst many others. And for the food lover spending time in Winchester would never be complete without a sampling of the famed Beer Cheese spread that forms an integral part of Kentucky cuisine.

Said to be created in Winchester in the 1940s, the annual Beer Cheese Festival in June is a staple of the town’s summertime events where thousands of people descend each year to sample various foods enhanced by this special dip and its variations.

Monticello

Wayne County courthouse in Monticello, By I, W.marsh, CC BY-SA 3.0, https://commons.wikimedia.org/w/index.php?curid=2483540
Wayne County courthouse in Monticello, By I, W.marsh, CC BY-SA 3.0, File:Wayne County Kentucky courthouse.jpg - Wikimedia Commons

Affectionately known as the “Houseboat Capital of the World”, the town of Monticello is located along the reservoir Lake Cumberland. Home to just over 5,700 residents and founded in the year 1801, Monticello was named after the home and plantation of Thomas Jefferson who was elected President that same year. Today this charming historic town and seat of Wayne County is a splendid place to spend a weekend where loads of welcoming hospitality and historic intrigue await. Visit such sites like the John Mill Log Cabin from the early 1800s, stroll through a number of alluring 19th century buildings, or of course simply spend time on the water. Here swimming and sailing are always popular, while a rental of a houseboat may be just the thing to complete one’s total immersion into the charm of this Kentucky gem.

Eddyville

Lyon County Courthouse in Eddyville, Kentucky
Lyon County Courthouse in Eddyville, Kentucky

Eddyville is the seat of Lyon County and was first settled in 1798; today this town of just under 2,500 residents remains one of Kentucky’s most splendid places. Located very near the reservoir Lake Barkley visitors can partake in fun opportunities for sailing and fishing, making Eddyville an ideal stopover for a weekend. In addition to the number of historic buildings in town, guests can also enjoy an assortment of great local restaurants, charming stores, and fine art galleries. Meanwhile the imposing and historic Kentucky State Penitentiary (opened in 1889) continues to stand sentinel in town and is one of the United States’ oldest continuously operating prisons.

Ashland

Ashland Kentucky Waterfront Park along the Ohio River
Ashland Kentucky Waterfront Park along the Ohio River

With a history dating to 1786, Ashland is indeed one of Kentucky’s oldest settlements. Situated along the southern banks of the Ohio River near the border with the West Virginia and Ohio, this charming mid size town of just over 21,000 residents is a great place of discovery. Known for its hot summers and mild winters, visitors can enjoy such places like the 47 acres Central Park where loads of outdoor activities are always popular choices.

In addition with a number of great annual festivals, there is always something fun to do in Ashland. Take in such events like the winter Festival of Trees or the Firkin Fest Craft Beer Festival, while an afternoon at the Highlands Museum and Discovery Center is a great way to entertain the youngest and oldest in the family.

A prominent component of the southeastern United States, the stunning State of Kentucky is a land full of natural wonder and historic intrigue. Indeed as the 15th State admitted to the Union in 1792, the stories and growth of Kentucky forms part of the greater story of America. This is most evident in Kentucky’s historic towns where beautiful surroundings meet with splendid local history creating a portrait of the USA unlike any other. From the tasty samplings of Beer Cheese in Winchester to the river beauty of Cadiz, these historic Kentucky towns will surely make one fall in love with the beauty that is the “Bluegrass State”.

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