Nestled along the banks of the Ohio River, Maysville, Kentucky has recently been named the “Best Small Town” in the state for 2025. Famed for its picturesque setting, rich heritage, and vibrant downtown, Maysville marries classic Americana charm with a spirit of cultural innovation. Travelers and Kentuckians alike are finding renewed fascination in this small riverside city, drawn by its history, hospitality, and a calendar packed with things to see and do.
A Storied History
Maysville’s narrative begins in the late 18th century, with Kentucky’s settlement by legendary frontiersmen like Simon Kenton and Daniel Boone. Founded initially as Limestone, the town became a vital entry point for pioneers crossing into Kentucky from the Ohio River. By the early 1800s, it was a lively hub for river commerce—shipping bourbon, hemp, and tobacco across the region and even influencing the ironwork found in great cities like Cincinnati and New Orleans.
Crucially, Maysville played an important role in the Underground Railroad. Its location on the river made it a key crossing point for enslaved people seeking freedom in the North. The haunting memories of this chapter are preserved in local museums and referenced in Harriet Beecher Stowe’s seminal work, Uncle Tom’s Cabin.
Architecture & Downtown Magic
One of the great joys of Maysville is its beautifully preserved downtown. Historic districts like Old Washington are living museums, with 18th- and 19th-century architecture housing everything from cozy cafes to eclectic shops. Unlike many towns, Maysville’s “full set of teeth”—a term locals use—means nearly all original buildings remain, creating a seamless streetscape full of character.
Downtown, you’ll also discover artistic treasures and cultural venues that belie the town’s small size. The Washington Opera House hosts Kentucky’s longest-running community theater, while the Russell Theater screens classic films. The EAT Gallery, Kentucky Gateway Museum Center, and the world-renowned Kathleen Savage Browning Miniatures Collection are must-visits for history buffs and the creatively inclined.
The Birthplace of Bourbon
Maysville’s claim as the birthplace of bourbon is embraced with pride. Old Pogue Distillery—family run for six generations—offers buyers the chance to sip bourbon with the same river view as those who crafted it a century ago. The annual Simon Kenton Festival, along with bourbon tastings and tours at the Old Pogue Experience, highlight this local legacy every fall.
Nature and Riverside Beauty
Maysville is also a destination for lovers of the outdoors. The Cummins Nature Preserve and the scenic Limestone Landing Park provide hiking, bird-watching, fishing, and tranquil river views. Every aspect of local culture seems touched by the river, from the famous Simon Kenton Bridge to the town’s dynamic murals depicting Maysville’s unique past.
Warmth and Community
Beyond the sights and stories, it’s the welcoming spirit of Maysville that continually charms visitors. Whether stopping by the historic Bank of Maysville (still with its original marble floors and brass fittings), enjoying muffins at the Park Café, or catching a performance by the Maysville Players, guests find a town that celebrates both its traditions and a vibrant modern revitalization.
Plan Your Visit
From its intriguing past to its diverse present, Maysville stands as a testament to what makes small-town Kentucky so unforgettable. For anyone plotting a Kentucky adventure in 2025, this charming riverside gem is a can’t-miss destination that genuinely earns its newfound title as Kentucky’s best small town.
Sources
[1] https://www.pbs.org/video/maysville-recognized-as-best-southern-small-town-ohuzgj/
[2] https://www.countryliving.com/life/travel/a62831376/best-small-towns-in-america-2025/
[3] https://10best.usatoday.com/awards/best-small-town-in-the-south/
[4] https://kids.kiddle.co/Maysville,_Kentucky
[5] https://traveltasteandtour.com/2025/06/maysville-is-a-hidden-gem-of-kentucky-history/
