The College of Southern Maryland maintains a growing satellite campus within city limits, including an aquatic center.

An upscale home development located in the Breton Bay area is just outside town, notable for both its country club golf course and swimming pool.

Leonardtown's population has grown significantly since 1990 as a result of the town's proximity to Patuxent River Naval Air Station and the Washington metro area.

[4] The primary method of travel to and from Leonardtown is by road, and three state highways serve the town directly.

Heading north, MD 5 provides connections to U.S. Route 301 in Waldorf and Interstate 95/Interstate 495 (the Capital Beltway) near Washington, D.C.

During the late 17th century, it appears that court was held at various homes throughout Newtown, and that it was only in 1708 that an official town with a designated courthouse was established.

It was during this same year that Phillip Lynes, then Mayor of St. Mary's City, Maryland's colonial capital, designated fifty acres of land at the head of "Brittons Bay" to be divided into 100 lots.

He further ordered that one lot be set aside for a county courthouse to be built at an expense not to exceed 12,000 pounds of tobacco.

In the decades that followed, Leonard Town became the place where local residents conducted their official business with the colony.

During the American Civil War, a Union Naval contingent occupied Leonardtown, searching all houses for weapons and supplies intended for shipment across the Potomac River to Virginia as Southern Maryland and the town's sympathies lay with the Confederacy.

Historic Leonardtown remains the only incorporated municipality in St. Mary's County with its own elected mayor and town council.

The town is experiencing a renaissance of its downtown as witnessed by recent openings of several new restaurants and businesses, some of which are located in historic buildings.

[6] The Naval Air Base located at Patuxent River has boosted the economy in Leonardtown significantly.