Maryland Loyalists Battalion The First Battalion of Maryland Loyalists ( as they were commissioned by the British army and referred to in Capt . Caleb Jones ' Orderly Book ) was a provincial regiment made up of colonial Americans , who remained loyal to Britain during the American Revolutionary War . Background . As with other colonies in British North America , Maryland was bitterly divided by the American Revolution . Members of the existing political elite tended to make reluctant revolutionaries ; men such as Benedict Swingate Calvert , illegitimate son of the ruling Calvert family and a Judge of the Land Office , remained Loyal to the British Crown , and would suffer the consequences . Like other loyalists , Calvert would find himself on the losing side of the Revolutionary War , which would effectively end his political career . The Annapolis Convention of 1774 to 1776 would see the old Maryland elite overthrown – men like Calvert , Governor Eden and George Steuart were all to lose their political power , and in many cases their land and wealth . After the war , Loyalists would have to pay triple taxes and were forced to sign the loyalty oath . Many had their lands and property confiscated . Formation of the First Battalion of Maryland Loyalists . The First Battalion of Maryland Loyalists was composed primarily of colonists from the Eastern Shore of Maryland ; it was commissioned in British - held Philadelphia in Mid - October , 1777 as " The First Battalion of Maryland Loyalists . " The unit ' s commander , Lt . Col . James Chalmers of Newtown , Maryland , ( today known as Chestertown , Maryland ) , was an active loyalist writer . The regiment saw limited action before being shipped off to Pensacola , Florida , to fight the Spanish in the fall of 1778 . A number of soldiers of the regiment died of smallpox upon arrival . Their garrison was subsequently defeated by the Spanish . After a brief time as prisoners in Cuba , the Maryland Loyalists were eventually sent back to New York City , the command center for British forces in the war . After the war , the members of the regiment , along with many loyalists from various colonies , were transported by the British Government as refugees to Nova Scotia . In the fall of 1783 , a ship carrying members of the First Battalion of Maryland Loyalists was shipwrecked off the coast of Nova Scotia . The survivors made up the first citizens of a new province : New Brunswick . The Maryland Loyalist Battalion is also a Revolutionary War reenacting unit based in Baltimore , Maryland . Notable members . James Chalmers author of a political pamphlet from 1776 entitled " Plain Truth " a rebuttal of Thomas Paine ' s popularist pamphlet " Common Sense " . One of the more dramatic persons to serve with the unit was a young ensign named William Augustus Bowles who would become a leader of the Creek Indians in the 1790s . Part of the confusion with William Augustus Bowles and piracy may stem from the British Army rank of " ensign " , which Americans attribute to the modern naval rank . Thus William Augustus Bowles , having a name some think was bastardized to " Billy Bowles " and then into " Billy Bowlegs . Billy Bowlegs was in fact a Seminole Chief in Florida , and was born five years after the death of William Augustus Bowles . There is no connection for either of them to piracy . One of the captains in the Maryland Loyalists was an attorney from Annapolis named Philip Barton Key . He was the uncle of Francis Scott Key who would later pen the words to " The Star Spangled Banner " .