Emerging Revolutionary War welcomes back guest historian Drew Palmer. He is the founder of Revolutionary Maryland; click here to learn more about that blog.

In the early evening of March 5, 1776, two armed boats left Annapolis to patrol the Chesapeake Bay. Captain John Pitt and Joseph Middleton were patrolling to prevent any British ships nearby from entering Maryland’s waters.  As they patrolled, they discovered an alarming sight: three British warships heading directly towards Annapolis. Middleton and Pitt rushed off to the Maryland Council of Safety’s chambers in Annapolis to report the startling news.¹ In the coming days, Maryland was tested for the first time in the growing Revolutionary conflict.

The American rebellion had become a full-scale war by the spring of 1776. In early March, the siege of British-held Boston was about to end. Hundreds of miles south in Philadelphia, the Declaration of Independence was only four months away. In Maryland, politicians worked hard to maintain Maryland’s isolation from the worst of the conflict. In Virginia, a raiding war had already begun. Only two months before, the town of Norfolk, Virginia, was bombarded, leading to the destruction of the town. Along with Norfolk’s destruction, British attacks and raids were carried out throughout the lower Chesapeake Bay, along with a blockade. ²

Participating in British operations in the lower Chesapeake was Captain Mathew Squire of the British Royal Navy. For several months, Squire’s vessel, the  Otter, served as the headquarters of the exiled Virginia Governor, Lord Dunmore. From the Otter, British attacks and raids were launched on Patriot strongholds in the lower Chesapeake. By March, Squire had gained a reputation as a competent officer and ruthless raider of American shipping.³ Squire was heavily involved in the bombardment of Norfolk and an attempted attack on Hampton, Virginia. Though Squire’s area of operation had been centered on the lower Chesapeake, new intelligence pulled him northward into Maryland.

Continue reading “The Defense of the Upper Chesapeake: Maryland’s First Trial in the Revolutionary War” →