1634 In November 1633, over 150 European settlers left England aboard the ARK and DOVE ships and arrived in early March 1634 at St. Clement’s Island in Colton’s Point, Maryland. On March 25, 1634, special ceremonies took place. One of the passengers, Maryland’s first Governor Leonard Calvert, read Lord Baltimore’s instructions, took formal possession of the new colony from this location and declared religious freedom for all. We celebrate Maryland Day every year since then because of all that happened that day on historic St. Clement’s Island. On March 27, 1634 they sailed to their new permanent settlement, St. Mary’s City, to establish a government with toleration and a new kind of life in America than they had experienced in England.
1637 St. Mary’s City became the first state capital and first county seat in Maryland. The government in the new colony formed and St. Mary’s County became the official name of the new county.
1654 St. Mary’s County Court was held in the homes at New Towne, overlooking Breton Bay since there was no courthouse built at that time. First, they met at the house of John Hammond and in 1677 at the house of Stephen Murty.
1695 The state capital was moved from St. Mary’s City to Annapolis, Maryland, which is presently our state capital. In Annapolis, the General Assembly is made up of State Senators and Delegates. Currently, Senator Roy Dyson serves as our State Senator.

Annapolis was originally named Anne Arundell Towne after Lady Anne Arundell, wife of Cecil Calvert, Second Lord Baltimore and founder of the Maryland colony. In 1694, the General Assembly designated Anne Arundell Towne as the capital. Queen Mary died the same year. After her death, the name changed to Annapolis in honor of her sister, Princess Ann, the new heiress to the throne.

1708 St. Mary’s Countians petitioned that a town be erected at a place on Breton Bay on land called Sheppard’s Old Fields. Philip Lynes, Mayor of St. Mary’s City, designated 50 acres of land at the head of Breton Bay to be laid out moving the county seat, including setting aside one lot for the first Commissioned County Courthouse to be built at an expense not to exceed 12,000 lbs of tobacco. The Governor and General Assembly charged seven commissioners with building the courthouse. Mayor Lynes suggested that the town to be named Seymour Town in honor of Governor John Seymour, who was serving as Governor at that time and who also, happened to be his brother-in-law.
1710 The first log courthouse was completed in Seymour Towne, otherwise known as Sheppard’s Old Fields, on the site of the present Courthouse in Leonardtown.
1728 In October, the legislature took up an act for the laying out of land, and erecting a town in St. Mary’s County, at a place formerly called Seymour Town. This was the founding of Leonard Town. Founders Day is celebrated October 28th.
1736 The General Assembly empowered the justices of St. Mary’s County to replace the wooden courthouse with a brick courthouse.
1858 An act to incorporate Leonardtown passed February 12, 1858. The first town election was held May 3, 1858.