century and a half ago, the path of the railroad was critical to the success of any community. Trains connected the country, hauling both passengers and freight. Towns were often built around the railroads, and depots soon followed.

Winchester was no different.

In 1872, Winchester’s original depot was built to serve the Elizabethtown, Lexington and Big Sandy Railroad. Through acquisitions and mergers, the depot eventually served two railroad companies: the Louisville and Nashville, and the Chesapeake and Ohio.

After three decades of service, the depot’s best days were behind it. The L&N finally replaced it with a new depot in 1907 for a cost of $10,206.06.

Winchester’s railroad history continued for decades for passengers, freight and the famous.

In 1948, President Harry S. Truman famously stopped in Winchester as part of his whistle-stop campaign for a full term as president. Though his stop was only supposed to be six minutes, it grew to 11 minutes as he spoke to a reported 6,000 people from the back of the train along Depot Street.

Fast forward to the 1980s, and the depot sat empty.

Several groups in town wanted to restore and preserve the building for a variety of uses including public meeting space. Others were trying to add it to the National Register of Historic Places. A developer was reportedly interested in converting it to a restaurant.

City leaders were busily negotiating with the L&N to purchase the depot and felt confident a final deal was imminent.

Things did not work out as everyone hoped.

Early on the morning of Saturday, July 25, 1981, a crew hired by the railroad came to Winchester and demolished the depot with no advance warning.

Mayor Carroll Ecton said he was shocked and believed he had a verbal agreement with the railroad to buy the depot for $1.

A railroad spokesman said the depot was torn down to allow the railroad to realign the tracks along Depot Street.

Residents were dismayed by the action and held a public “funeral” for the depot a couple days later.

Decades later, the surprise demolition of the depot brings a tinge of sadness to long-time residents as they remember what used to fill a large part of downtown Winchester. §