Leonardtown History

Leonardtown, Maryland, boasts a fascinating history spanning over three centuries. Founded in 1708, this charming waterfront town has played a significant role in Maryland's colonial and early American history.

Early Beginnings

Originally known as Seymour Town, in honor of Governor John Seymour, the area that would become Leonardtown was first settled in the mid-17th century[^5]. By 1654, county court sessions were being held in the homes of local residents in an area called "Newtown" or "Newtowne Hundred".

In 1708, the town was officially established when Philip Lynes, then Mayor of St. Mary's City, designated 50 acres of land at the head of Breton Bay to be divided into 100 lots. One lot was set aside for a county courthouse, to be built at an expense not exceeding 12,000 pounds of tobacco.

From Seymour Town to Leonardtown

The town's name evolved over time. Initially called Seymour Town, it was renamed Leonard Town in 1728, in honor of Benedict Leonard Calvert, who was Maryland's governor at the time. This name eventually became Leonardtown, as we know it today.

A Hub of Activity

Throughout the 18th and 19th centuries, Leonardtown served as a bustling port and the center of local government. Farm products were regularly shipped through the port, and the town became the place where residents conducted their official business with the colony.

Challenges and Growth

Leonardtown faced its share of challenges during major conflicts. In the War of 1812, the town was invaded by 1,000 British Marines, crippling the local economy[^9]. During the Civil War, Union Naval forces occupied Leonardtown, searching houses for weapons and supplies intended for the Confederacy, as Southern Maryland's sympathies lay with the South.

Despite these setbacks, Leonardtown continued to grow. By 1860, the town boasted approximately 35 dwellings, a county newspaper, two hotels, and several stores.

The Steamboat Era

In the late 19th and early 20th centuries, Leonardtown thrived as a steamboat landing. Steamboats carried goods and passengers throughout the Chesapeake Bay area, contributing to the town's economic vitality. A unique attraction during this period was a floating theater that docked annually at the port, providing entertainment for locals and visitors alike.

Leonardtown Today

Today, Leonardtown beautifully preserves its rich history while offering modern amenities. Visitors can explore historic sites such as Tudor Hall, the Old Jail Museum, and St. Aloysius Catholic Church, dating back to 1766. The town is also home to the charming Port of Leonardtown Winery, set in a historic schoolhouse.

Leonardtown's commitment to preserving its heritage is evident in its designation as the only Arts and Entertainment district in Southern Maryland and its status as an officially designated Main Street America destination. With its blend of history, culture, and small-town charm, Leonardtown continues to live up to its early 18th-century moniker as "a most convenient place".

As you explore Leonardtown, you'll find a town that has not only witnessed history but continues to make it, offering visitors a unique glimpse into Maryland's past while embracing its promising future.