There are a wide variety of flags that graced the fields, forts, ships and buildings of the American Revolution. Some were simple affairs, created from extant flags with a bit of paint or cloth, others were complex examples of silk with hand painted artwork. Aside from the really awesome designs and variety on the American side...one stuck out in particular. Who knows if it ever existed. It might have, but the only record is a contemporary engraving.
A British Red Ensign as used in Colonial America
British flags in the American Colonies were taken, converted, and used by our forefathers to proclaim a new country and a new found liberty. The Red Ensign...the British flag of the American Colonies, had the union stripped off in some cases and the phrase "LIBERTY" applied in either cloth or paint. The Taunton flag and the Huntington flag are two examples...
Boston Evening Post - October 24th, 1774:
The Taunton Flag
The Huntington flag was a similar case. Again, a British flag was taken, the Union portion in the upper corner was removed, and the word LIBERTY was applied. This flag, apparently went into battle, as was captured by Hessian troops on Long Island. It existed in a museum in Dresden, Germany...until the firebombing of 1945...
The Huntington Flag
And then...there is a mystery...
Amos Doolittle was an engraver from Connecticut, New Haven to be exact. His most famous artistic works are a series showing the Battles of Lexington and Concord in April of 1775. They are most important because he actually witnessed the events. His interpretation of the action on Lexington Green shows in all likelihood the truth of that event, which has changed significantly over the centuries. Doolittle's interpretation shows the Continentals fleeing the field in fear and disarray, an event that has changed to noble engagement of Patriots standing their ground against the might of the British Empire, never wavering in the face of the King's redcoats. I tend to believe the former, and as Doolittle was an eyewitness, I'm fairly confidant and agree with his version, especially when it is paired with contemporary written accounts. The Lexington Militia probably high-tailed it off the field directly after the first British volley...that is to say...the first shot. Don't get me wrong, this doesn't diminish those brave Patriots...they stood against the Regulars, and that took guts...and the day's events culminating in devastating defeat for His Majesty and his men.
This collection of artwork is the closest visual account we have to the events of that day. There is also another engraving attributed to Doolittle, called The Retreat. It is a satirical piece, portraying the fleeing British troops as jackasses (literally) looting, burning...running away in the face of stiff Patriot resistance.
In the engraving, Doolittle depicts a very interesting flag carried by the Colonials...it appears to be a British Regimental color, a military flag, with the word "Liberty" right in the middle. If this flag really existed, no record has been found to determine where it originally came from, or how it was acquired by the colonials. One could suggest that it was a captured flag, which is possible...but very, very unlikely. It would have had to be a quick paint job in the field as well, slopping that word on...then turning it against its former owners. I do not think this is the case. Like the Taunton and Huntington flags, the Doolittle flag may have been a converted Red Ensign. If the drawing is even remotely accurate as to size, I believe the Colonials cut the Union canton (the part of the flag up in the corner) from an existing flag, painted or sewed the word "Liberty" on their new creation, and took it into battle. That is IF, the drawing can be believed. Flag were relatively rare in the American colonies. Generally, you saw a flag on a ship or a statehouse...that was it. Unlike today, not every house had flag out front. If someone had squirreled away a British Red Ensign, it is very likely that the Doolittle flag did exist. As to size, the drawing would be accurate, as British Red Ensigns ranged to as long as 50 feet...yes, fifty feet! So looking at the Doolittle engraving and the size of what would be just a piece of a larger flag, this theory makes a bit more sense than the American Colonial Militia capturing and modifying a British Military flag on the the very first day of the War.
Again, there is no proof the Doolittle flag existed, aside from the drawing. All we have is a contemporary artist's satirical impression, and who knows, it being a "cartoon" might simply justify the addition of a fantasy flag to drive home the point of the farce. Then again, maybe Doolittle really did see American militia carrying a converted British flag in battle, as was the case with the Huntington color. He certainly portrayed the serious events of that day accurately enough...