The following is a timeline of the history of the region of Southern Maryland.
3rd century
200 - Beginning occupation of a Piscataway village near present-day Biscoe Gray.
14th century
1330 - Beginning occupation of the Piscataway village Moyaone.William and Mary Center for Archaeological Research. "Return to Potomac Creek (44ST2): Archaeology at a Late Prehistoric Native American Village ." Virginia Department of Historic Resources.
17th century
1600-1649 1608 - John Smith and William Caliborne make contact with the Piscataway. 1623 - Moyaone is burned to the ground by Virginian colonists, the village would be rebuilt upon the same site. 1632 - Charles I of England deeds the land of Maryland to George Calvert, 1st Baron Baltimore. 1634 - The Ark and the Dove ships bring people to Southern Maryland, among them Leonard Calvert and Mathias de Sousa This would lead to the settling of St. Mary's City on the site of the abandoned village of Yacomoco. 1636 - The Piscataway tayac Wannas is murdered by his brother Kittamaquud, who goes on to rule in his place. 1640 July 5 - Kittamaquund is baptized by Jesuit Andrew White. 1641 - The Piscataway tayac Kittamaquund dies. 1642 - Mathias de Sousa votes as a freeman in the Maryland Propriety Assembly. 1644 - Beginning of Plundering Time that saw Richard Ingle temporarily take control of St. Mary's City.Claiborne, J. Herbert. “William Claiborne of Kent Island.” The William and Mary College Quarterly Historical Magazine, vol. 1, no. 2, 1921, pp. 74–99. JSTOR, https://doi.org/10.2307/1923023. Accessed 3 Feb. 2025. 1646 - Leonard Calvert regains control of St. Mary's City. 1649 April 12 - Maryland Toleration Act is passed in St. Mary's City.
1650-1699 1650 - Anne Arundel County is organized.Anne Arundel County Maryland - Our Early Settlers, Maryland Genealogy Trails, accessed April 2018. 1654 - Calvert County is organized. 1658 April 13 - Charles County is organized. 1666 April 20 - The 1666 Articles of Peace and Amity is signed between Maryland's government and 12 Eastern Algonquian-speaking Indigenous nations, including the Piscataway, Anacostanck, Doegs, Mikikiwomans, Manasquesend, Mattawoman, Chingwawateick, Hangemaick, Portobackes, Sacayo, Panyayo, and Choptico. 1669 - Piscataway Manor, an Indian reservation, is established. While centered on the former Piscataway city of Moyaone, the area would also include people of the 12 Eastern Algonquian-speaking Indigenous nations from the 1666 peace treaty. 1669 - The first Calvert County courthouse is built at Battle Town, near Battle Creek. 1675 - Cecil Calvert dies, Charles Calvert is sent to London to assume baronial rank, he would never return to Maryland 1676 - A group of Protestant Associators meet in Calvert County and publish Complaint from Heaven with a Huy and crye and a petitionout of Virginia and Maryland. 1681 - Maryland passes a law that children born to free black women and black children born to white women would be free. 1683 - Battle Town renamed "Calvertown." 1683 - Lower Marlborough is established. 1683 - Huntingtown is founded at the head of Hunting Creek. 1683 - Christ Church is established in Port Tobacco. 1685 October 9 - After being found guilty of bewitching Francis Sandsbury and others in Calvert County, Rebecca Fowler becomes the only person convicted and executed for witchcraft in Maryland. 1689 - Beginning of the Protestant Revolution in Maryland. 1692 - The Church of England is made the established church of the Maryland Colony. 30 Anglican Parishes are created, including St. James Parish in Lothian, St. Paul's Parish in Baden, and All Saints Parish in Sunderland. 1695 - Calvert County land is partitioned into parts of St. Mary's, Charles, and Prince George's counties, creating the boundaries of the county today. 1695 - Governor Francis Nicholson moves the colonial capital of Maryland from St. Mary's city to Annapolis. 1697 - Under the tayac Ochotomaquath, the Piscataway would come under the protection of the Onöndowa'ga:', and would flee north towards Pennsylvania. 1698 February - Local legend has it that Moll Dyer is chased from her home and supposedly dies kneeling on a rock in St. Mary's County.
18th century
1704 - Public worship of Catholicism is banned in Maryland. 1711 - After coming under the influence of the Great Law of Peace, the Piscataway become known by their anglicized Iroquois name "Conoy." 1718 - Roman Catholics are stripped of the right to vote in Maryland. 1721 March 19 - Upper Marlboro is designated the county seat of Prince George's county. 1725 November 5 - "Williams' Old Field" replaces Calvertown as the county seat for Calvert County following an Act of Assembly. 1728 October 30 - "Williams' Old Field" is renamed "Prince Frederick." 1732 - Construction completed for the Calvert County courthouse. 1732 November 4 - Thomas Johnson is born near St. Leonard's Creek. 1748 April 20 - Fire destroys Calvert County courthouse. 1776 - British troops land on St. George Island during the American Revolutionary War. They are later repelled by Maryland's Flying Camp militia under Rezin Beall. 1780 - British troops invade Calvert County, destroying property and burning buildings. 1783 - Maryland prohibits the importation of enslaved people. 1789 June 15 - Josiah Henson, who Harriet Beecher Stowe cites as being one of the inspirations for her 1852 novel Uncle Tom's Cabin, is born in Port Tobacco. 1779 January 14 - Joseph Kent is born in Calvert County. 1794 - Following the Battle of Fallen Timbers some members of the Piscataway tribe migrated south, returning to their ancestral lands in Maryland.
19th century
1800-1849 1814 June 8-10- Several attacks involving the Chesapeake Bay Flotilla take place near and around St. Leonard's Creek. During this time, many enslaved people living in Southern Maryland found freedom by fleeing to the British military. 1814 July 19- British burn the Prince Frederick Courthouse. At least 14 enslaved persons escaped to freedom via a British Vessel in Lower Marlboro. 1814 August - British soldiers arrive in Benedict and march north to Upper Marlboro. 1819 - Third Prince Frederick courthouse is constructed. 1837 - Charles Ball publishes his autobiography, “The Life and Adventures of Charles Ball." 1843 - Smithville United Methodist Church is built near present-day Dunkirk. 1845 July - Two enslaved men named Mark Caesar and Bill Wheeler lead a slave rebellion Charles County.
1850-1899 1853 - Charter granted to the Baltimore and Potomac Railroad with their right of way running from Baltimore to Pope's Creek in Charles County. 1858 February 12 - The town on Leonardtown is incorporated. 1863 October - Camp Stanton, a site created for the recruiting and training of African American men, is established near Benedict. 1864 November 1 - Maryland ratifies a new constitution that prohibits slavery. 1865 - St. Edmonds United Methodist Church is built in Chesapeake beach with assistance from the Freedman's Bureau. 1865 April 15 - John Wilkes Booth stops at St. Catharine, Samuel Mudd's house in Waldorf. 1866 August 8 - Explorer Matthew Henson is born in Nanjemoy. 1867 - Isaac Solomon started a commercial fishery on what was then referred to as "Somervell's Island" or "Sandy Island," later to be known as Solomon's Island. 1868 March 20 - Southern Maryland Railroad is incorporated, with plans to connect Washington, D.C. to Point Lookout in St. Mary's County. 1868 March 30 - Baltimore and Drum Point Railroad Company receives a charter to connect the two points. No construction is ever completed. 1869 - Wallville School opens in Calvert County serving as a one-room schoolhouse for African American students. 1870 - Construction completed on a Solomon's Island Post Office and a causeway connecting the island to Calvert County's mainland. 1877 - Issac Davis completes construction of the first framed bugeye, "Clyde," on Solomons Island. 1881 - Courthouse built in Upper Marlboro. 1882 March 3 - Calvert County courthouse destroyed, along with its records, in a fire. 1883 October - Trains begin running on the Southern Maryland Railroad from Brandywine to Mechanicsville. 1884 - Fourth Prince Frederick courthouse is constructed. 1885 September - St. Mary's Academy opens. 1886 - Post office opens in Shady Side. 1886 April 1 0 The Southern Maryland Railroad is sold and reincorporated into the Washington & Potomac Railroad. 1886 April 7 - The town of Chesapeake Beach is incorporated. 1886 June 6 - Charles Whitley is lynched in Prince Frederick. 1887 - Benjamin Hance is lynched in Leonardtown. 1888 March 6 - The town of Chesapeake Beach's incorporation is repealed. 1888 April 4 - The towns of La Plata and Port Tobacco Village are incorporated. 1890 - Drayden African American Schoolhouse is built in St. Mary's county. 1891 - State of Maryland grants a charter to the Washington and Chesapeake Beach Railway Company. 1890 - Indian Head Naval Surface Warfare Center opens. 1894 April 3 - The town of Chesapeake Beach is reincorporated with the help of the Washington and Chesapeake Beach Railway Company. 1895 - Turkey Tayac is born. 1896 - Chesapeake Beach Railway Company takes over charter from the Washington and Chesapeake Beach Railway Company. 1896 - British immigrant Joseph Cocking is lynched in Port Tobacco.
20th century
1900-1949 1900 - The steamboat J.S. Warden begins to take passengers from Baltimore to Chesapeake Beach. 1903 - The McDonough Institute, the first high school in Charles County and predecessor to Maurice J. McDonough High School, opens. 1910 - The town of North Beach is incorporated. 1911 - The Digges Amendment, drafted by Charles County politicians Walter Digges and William J. Frere is rejected by Maryland voters. The amendment attempted to disenfranchise African American voters. 1916 October - Following the razing of the fourth Prince Frederick Courthouse, the fifth, and current courthouse completes construction. 1920 - WWI Memorial Statue designed by Edward Berge is erected in font of the Calvert County Courthouse. The statue lists names of fallen White soldiers separate from fallen Black soldiers. 1920 April 16 - The town of Indian Head is incorporated. 1922 - Central Industrial School opened in Prince Frederick as a multi-room school for African Americans in Calvert County. 1923 March 30 - Belvedere Hotel in Chesapeake Beach is destroyed in a fire. 1924 - St. Mark's Chapel is built in Deale. 1925 - Chesapeake Biological Laboratory begins operations in Solomons. R.V. Truitt serves as the facility's first director.Cory Hall, University of Maryland Center for Environmental Science, retrieved July 9, 2010. 1926 - A tornado hits La Plata, destroying the La Plata Elementary School and killing thirteen school children. 1930 - Seaside Park opens in Chesapeake Beach. 1930's - Owings Eagles begin to play on Gray's Field. 1933 - Pomonkey High School opens as the first high School for African Americans in Charles County. 1933 August 23 - A storm hits Solomon's Island, destroying oyster beds and packing houses. 1934 - Wallville School ceases operations as a school. 1935 April 15 - The final train leaves the Chesapeake Beach Railway Station as Chesapeake Beach Railways closes down due to bankruptcy. 1937 - The Southern Maryland Electric Cooperative is established. 1937 December 27 - Calvert County agrees to equal pay for their African American school teachers following a suit from Harriet Elizabeth Brown and NAACP attorney Thurgood Marshall. 1939 - W. Sampson Brooks High School opens as the first high School for African Americans in Calvert County. 1940 December - Governor Harry W. Nice Memorial Bridge opens. 1941 - Riverside Airfield opens in Croom and becomes the first African American-owned and operated airfield in Maryland.