Taking an interest in the iron deposits around the Cumberland Gap around 1886, Arthur was able to convince some of the wealthy scions of Gilded-Age Asheville, North Carolina, to talk to their families about funding a "Pittsburgh of the South", but sufficient financing was not forthcoming.

[13] Simultaneously, he funded and began construction on the Powell's Valley Railroad, with the aim of connecting the Cumberland Gap region to Knoxville.

[17] Pianist Ben Harney is also claimed to have originated ragtime music in Middlesboro, where he played in local saloons in the early 1890s.

[18] Just south of the Cumberland Gap in the area of the present-day Lincoln Memorial University, a $1-million Four Seasons Hotel was built in 1892 with 500 rooms, a 200-room spa, and a sanitarium.

[14] Rebuilding from a devastating fire in 1890 used up more capital and time and the poor quality of local ore meant that revenue from Arthur's steel mills was insufficient to weather the Panic of 1893 on Wall Street.

[13] Arthur's development of the area finished, the post office was renamed the following year after the already-prevalent local spelling "Middlesboro".

[21] Despite being the largest city in the county, the development of Middlesboro came too late to avoid Pineville's being the seat of the local courthouse.

Middlesboro installed the first electric street cars west of Washington, D.C., to help locals and tourists visiting the city which became known as "Little Las Vegas" in the 1930s.

The town, under rule of the infamous Ball brothers, was featured in newspapers across the country as one of the deadliest, wildest cities in the United States.

It was one of the few cities in the Eastern Coal Fields to boast a grand opera house and it hosted one of the finest school districts in the state.

A grand centennial celebration was held in 1990 that included a ball, air show, and beauty pageant, as well as the dedication of a new city park.

Currently, Middlesboro is investing in downtown revitalization to help create new business and give the city a better image.

DDM also hosts numerous events for the community and the tri-state area that are free to the public, one of the most popular includes the Downtown Ducky Dash and Block Party.

DDM oversees all projects that take place within the downtown area and has plans to create brick stamped crosswalks at Fountain Square.

Ultimately, they plan to make the historic downtown area more pedestrian-friendly with more benches, bike racks, planters, and streetscape improvements in the works.

Recently, the organization has applied for nearly $1 million in grant money for the purpose of preservation and development of the general downtown district.

For many hours after the flood, travel in and around the city was very difficult due to large amounts of standing water in the basin that Middlesboro is built in.

A few days afterwards, Governor Steve Beshear toured the area and formally declared it a disaster, permitting state funds to be used in rebuilding.

The community organic garden was made possible through the City of Middlesboro, Bell County Health Department, and several donors and volunteers.

Middlesboro was featured on the History Channel's television series How the States Got Their Shapes in the episode "Forces of Nature".

[23] ABC's Good Morning America honored the Middlesboro-Bell County Library for participating in the "52 Weeks of Giving" program on May 27, 2013.

The concert venue is a formerly abandoned lot near the main intersection of town at 20th & Cumberland Ave. Middlesboro is one of 15 cities across the nation to be chosen for the Levitt AMP series.

With the recently completed renovations on U.S. 25E, travelers now have four-lane connection to Interstate 81 at Morristown, Tennessee, 45 miles (72 km) to the south.

The canal is home to numerous populations and species of ducks, all of which are considered to be honorary citizens of the city, despite the traffic headaches they may cause.

Middleboro's main thoroughfare is named Cumberland Avenue, which runs through Middlesboro's historic downtown district.

DDM has been around since 2004 and since then, has restored Middlesboro's famed Fountain Square, completed many historical murals in town, started and formed a farmer's market, updated signage in the downtown area, and received grants for new plantings for the numerous planters that line Cumberland Avenue.

The airport has recently undergone a major renovation, including the addition of a brand new terminal that features public restrooms, lounge, kitchen, and a radio room that can be used for up-to-date weather information.

The area also features Middlesboro Crossing, a recently constructed strip mall on the north end of the city.