This flag was in use in England since the Crusades and it was one of the national emblems of England as early as 1277. It continued to be the English national flag for almost 400 years. Sir Walter Raleigh and Sir Francis Drake flew this flag while exploring the New World. It was used at Jamestown until replaced by the new Union Flag (see below)

Using mercenaries to control conquered lands by private companies is not a new practice, and government hiring corporations to control colonies isn't new either. Parliament used the British East India Company to conquer and manage India, and later gave the company trade monopolies in parts of the New World to help pay them. The East India Company was expected to provide the necessary "soldiers for hire" to rule India, and profits made from exporting their Indian tea to the American Colonies helped pay for those soldiers.

With King James I inheritance of the English throne in 1603, the Cross of Saint George was placed over the Scottish Cross of Saint Andrew to form the British Union Flag. Although the traditional St. George's Cross flag continued as the national flag for some years, all seagoing ships began using the Union flag (better known today as the Union Jack). But in 1634, use of the Union Jack was restricted to only the King's Royal Navy ships, and its use by merchant ships was forbidden. The continued use of this flag by merchant ships commissioned by the Royal Governors in the American colonies would cause problems until a solution was found in 1707 (see below)

The Lord Baltimore flag combines the black and gold family arms of the Lords Baltimore, the colonial proprietors of Maryland, granted to the first Lord Baltimore - George Calvert in 1622. This flag was used to represent Maryland from the 1600's until the Revolutionary War when the United States was born and a national flag was used.

The "Pine Tree Flag" is a generic name for a number of flags used in New England from 1686 to 1776. The Sons of Liberty would first rally under a Pine tree they called "The Liberty Tree." This Pine Tree ensign was that of the Massachusetts Merchant Navy, but in April of 1776, it became the official flag of the short lived Massachusetts Navy which was destroyed by the British at the Battle of Penobscot Bay.

In 1701 another variant of the Union Jack was created for the use of ships commissioned by the governors of the North American colonies. It is unknown how much use this variant saw before the introduction of the Colonial Red Ensign by Queen Anne six years later.

The Bedford Flag may be the oldest complete flag known to exist in the United States. Physical and historical evidence dates it from early in the 1700s, and the Bedford Flag is similar to a flag described as having been used by a cavalry troop of the Massachusetts Bay Militia in the French and Indian Wars. It may well have been that flag. Further legend states that it was later carried by Bedford Minuteman, Nathaniel Page, to the Concord Bridge on April 19, 1775, at the beginning of the American Revolution. However, there is no proof, either from testimonies, depositions, diaries or memoirs written by any participants, mentioning any such flag flown that day.

The British Red Ensign, also known as the "Meteor" Flag, was adopted as the new flag for England and her colonies in 1707 at the request of Queen Anne. Because of this the flag also carries the name "Queen Anne's Flag." This was the first "national flag" to fly over the English American colonies.

Roger Williams stated the cross was a symbol of the antichrist, so John Endicott, the Governor of Massachusetts Bay Colony, ordered the cross removed from the Colonial Red Ensign. The Great and General Court of the Massachusetts Bay Colony found Endicott had "exceeded the lymits of his calling" and punished him by forbidding him to hold public office for one year. Then they gave the citizens permission to do as they wanted with the flag design, and without exception, they all removed the crosses from their flags.

This flag was used by Colonial merchant ships sailing out of New England ports as early as 1737. It is the earliest flag identified with all of New England and was flown by ships from both Rhode Island Colony and the Massachusetts Bay Colony.

The Calvert Arms/King's Colors has the antique gold and black diamonds of the Calvert coat of arms as the field. The Calverts were the Lords Baltimore, lords proprietors of the Royal Colony of Maryland. (This is the same design that is used in two quarters of the current flag of the State of Maryland, the other two quarters use the design of the "Crosslands.")

The Maryland Militia fought under the Calvert Arms/King's Colors in their expedition of 1754 and this may have been the first non-British flag to go into battle with George Washington. It was certainly used in King Philip's War of 1675 and in the later French and Indian War.