Middlesboro, Kentucky, (population 10,000) is a city located in Appalachian Kentucky. Daniel Boone blazed a trail through the Cumberland Gap and into the area in 1775. More than 250,000 settlers followed the Boone Trace in their journey west. The Wilderness Road Heritage Highway, a National Scenic Byway, begins in Middlesborough and largely follows the Boone Trace northeast to Berea.

Nearly a century later, in the 1880s, the founder of what was then called "Middlesborough," Alexander Arthur, had a vision for creating the "Pittsburgh of the Appalachians." His efforts led to the explosive growth of the town, with millions invested in factories, infrastructure, and buildings. Unfortunately, disastrous fires, floods, and the Panic of 1893 curtailed Arthur's plans. Those who stayed after the crash found themselves with more resources than they could maintain less than a decade after the town was founded.

Ben Harney invented Ragtime music here between 1890 and 1893. In 1902, the notorious Quarterhouse Battle erupted nearby, pitting city folks against mountaineers and coal miners. During the period that followed, Middlesboro became known as a "Little Las Vegas." Al Capone's arch rival, Jack Zuta, lived and worked in Middlesboro before moving to Chicago around 1915. Zuta is now buried in the Jewish Cemetery. 

In the 1980s and 1990s, downtown Middlesboro faced many challenges, including an F5 tornado. Local leaders rallied to form Discover Downtown Middlesboro in 2006 to help revitalize the commercial district. One highlight of their work was Better Block Middlesborough, modeled after other Better Block events around the U.S. More than 100 volunteers worked to demonstrate that temporary interventions can help encourage civic participation and plant the seeds of long-term transformation. Added to this program was an emphasis on integrating historic preservation goals into the local event.

The Park Theater, closed for 30 years, was cleaned, painted, and reopened for a screening of It's a Wonderful Life. Another vacant building was transformed into a pop-up shop for the weekend, helping to demonstrate that neglected, overlooked buildings could serve contemporary purposes. Heritage tourism was advanced through the creation of a two-mile History Walk, passing through the most historic areas Downtown. A red dotted line was painted on the sidewalk and temporary historical markers were posted at select sites, sharing stories about forgotten local history.

The program was repeated in May 2014, this time focusing on the preservation of the Elks Home. A Makers' Market was started in a vacant storefront, highlighting the work of local artists, crafters, and food producers.

Middlesboro has made a complete inventory of historic properties available to the public online using a Web-based survey program. Present day photos and descriptive data for more than 250 buildings and sites have been uploaded, along with legacy data from the Kentucky Heritage Council. The Bell County Historical Society, housed in a former Carnegie Library saved from demolition, has an archive and local history exhibits, and the Middlesborough Little Theater has commissioned and presented several plays focused on the history of the community.

The City is a Certified Local Government and recently completed a five-year Historic Preservation Plan. More than 20 constituent groups are named and have specific tasks in carrying out the plan. Both this plan and the Downtown Middlesboro Strategic Plan call for creating a full-time position for a preservation professional within city government in the next five years.

Middlesboro is part of Tour Southern and Eastern Kentucky, a regional group promoting heritage tourism, adventure tourism, agritourism, arts, and culture in a 50 county area. A driving trail and a two-mile walking loop through the downtown guide visitors past local historic sites.

Designated a Preserve America Community in December 2014.

For more information

City of Middlesboro

Discover Downtown Middlesboro

Better Block Middlesborough (video)

Historic Properties of Middlesboro