In 1777, William Keeling, a 34 year old Black man ran away from Grumbelly Keeling, a slaveowner on the Eastern Shore of Virginia, which covers a very small area.  The Keelings were an old maritime family within Princess Anne County. William, and possibly his wife Pindar, a “stout wench” as the British described her, would be evacuated July 1783 on the Clinton ship from New York with British troops and other supporters of the British Crown (“Loyalists”) likely to somewhere in Canada.  They were not the only ones. This article does not advocate for the “loyalist” point of view, but rather just tells the story of Blacks who joined the British Crown in a quest to gain more freedom from their bondage rather than the revolutionary cause. 
Black families go to freedom
There were a number of other Black families that left the newly independent colonies looking for freedom. Many of these individuals, described by slaveowners as “runaways,” had fled to British lines hoping for Freedom. Perhaps they saw the colonies as a “land of black slavery and white opportunity,” as Alan Taylor put it, seeing the British Crown as their best hope of freedom.  After all, slavery was legal in every colony, up to the 1775, and continuing throughout the war, even as it was discouraged in Massachusetts after the Quock Walker decision in 1783. They likely saw the Patriots preaching for liberty and freedom as hypocrites, with some of the well-off individuals espousing these ideals owning many humans in bondage.
There were 26 other Black families who passed through Annapolis on their way north to Nova Scotia to start a new life. When they passed through the town, they saw as James Thatcher, a Surgeon of the Continental Army described it on August 11, 1781, “the metropolis of Maryland, is situated on the western shore at the mouth of the river Severn, where it falls into the bay.”
The Black families ranged from 2 to 4 people. Their former slavemasters were mainly concentrated in Portsmouth, Nansemond, Crane Island, Princess Ann/Anne County, and Norfolk, all within Virginia, as the below chart shows:
Of these slaveowners, it is clear that the Wilkinson family was Methodist, as was the Jordan family, but the Wilkinsons were “originally Quakers” but likely not by the time of the Revolutionary War. The Wilkinson family was suspected as being Loyalist “during the Revolution” with “Mary and Martha Wilkinsons (Wilkinson)… looked on as enemies to America” by the pro-revolutionary “Patriot” forces. However, none of the “Wilkinsons became active Loyalists.” Furthermore, the Willoughby family may have had some “loyalist” leanings, with other families were merchant-based and had different leanings. At least ten of the children of the 26 families were born as “free” behind British lines while at least 16 children were born enslaved and became free after running away for their freedom. 
Beyond this, it is worth looking at how the British classified the 31 women listed in the “Book of Negroes” compiled in 1783, of which Annapolis was one of the stops on their way to Canada. Four were listed as “likely wench[s]” , four as “ordinary wench[s]”, 18 as “stout wench[s]”, and five as other. Those who were “likely wench[s]” were likely categorized as “common women” (the definition of wench) rather than “girl, young woman” since all adult women were called “wench” without much exception.  As for those called “ordinary” they would belong to the “to the usual order or course” or were “orderly.” The majority were “stout” likely meaning that they were proud, valiant, strong in body, powerfully built, brave, fierce, strong in body, powerfully built rather than the “thick-bodied, fat and large, bulky in figure,” a definition not recorded until 1804.
Fighting for the British Crown
When now-free Blacks, most of whom were formerly enslaved, were part of the evacuation of the British presence from the British colones from New York, leaving on varying ships, many of them had fought for the British Crown within the colonies. Among those who stopped by Annapolis on their way North to Canada many were part of the Black Brigade or Black Pioneers, more likely the latter than the former.
The Black Pioneers had fought as part of William Howe’s army, along with “black recruits in soldiers in the Loyalist and Hessian regiments” during the British invasion of Philadelphia. This unit also provided “engineering duties in camp and in combat” including cleaning ground used for camps, “removing obstructions, digging necessaries,” which was not glamorous but was one of the only roles they played since “Blacks were not permitted to serve as regular soldiers” within the British Army. While the noncommissioned officers of the unit were Black, commissioned officers were still white, with tank and file composed mainly of “runaways, from North and South Carolina, and a few from Georgia” and was allowed as part of Sir Henry Clinton‘s British military force, as he promised them emancipation when the war ended. The unit itself never grew beyond 50 or go men, with new recruits not keeping up from those who “died from disease and fatigue” and none from fighting in battle since they just were used as support, sort of ” garbage men” in places like Philadelphia. The unit, which never expanded beyond one company, was boosted when Clinton issued the “Phillipsburgh Proclamation,” decreeing that Blacks who ran away from “Patriot” slavemasters and reached British lines were free, but this didn’t apply to Blacks owned by “Loyalist” slavemasters or those in the Continental army who were “liable to be sold by the British.” In December 1779, the Black Pioneers met another unit of the same type, was later merged with the Royal North Carolina Regiment, and was disbanded in Nova Scotia, ending their military service, many settling in Birchtown, named in honor of Samuel Birch, a Brigadier General who provides the “passes that got them out of America and the danger of being returned to slavery.” Thomas Peters, Stephen Bluke, and Henry Washington are the best known members of the Black Pioneers.
The Black Brigade was more “daring in action” than the Black Pioneers or Guides. Unlike the 300-person Ethiopian Regiment (led by Lord Dunmore), this unit was a “small band of elite guerillas who raided and conducted assassinations all across New Jersey” and was led by Colonel Tye who worked to exact “revenge against his old master and his friends” with the title of Colonel a honorific title at best. Still, he was feared as he raided “fearlessly through New Jersey,” and after Tye took a “musket ball through his wrist” he died from gangrene in late 1780, at age 27. Before that happened, Tye, born in 1753, would be, “one of the most feared and respected military leaders of the American Revolution” and had escaped to “New Jersey and headed to coastal Virginia, changing his name to Tye” in November 1775 and later joined Lord Dunmore, The fighting force specialized in “guerilla tactics and didn’t adhere to the rules of war at the time” striking at night, targeting slaveowners, taking supplies, and teaming up with other British forces. After Tye’s death, Colonel Stephen Blucke of the Black Pioneers replaced him, continuing the attacks long after the British were defeated at Yorktown.
After the war
Many of the stories of those who ended up in Canada and stopped in Annapolis are not known. What is clear however is that “an estimated 75,000 to 100,000 black Americans left the 13 states as a result of the American Revolution” with these refugees scattering “across the Atlantic world, profoundly affecting the development of Nova Scotia, the Bahamas, and the African nation of Sierra Leone” with some supporting the British and others seized by the British from “Patriot” slaveowners, then resold into slavery within the Caribbean sea region. Hence, the British were not the liberators many Blacks thought them to be.Still, after the war, 400-1000 free Blacks went to London, 3,500 Blacks and 14,000 Whites left for Nova Scotia and New Brunswick, where Whites got more land than Blacks, some of whom received no land at all. Even so, “more than 1,500 of the black immigrants settled in Birchtown, Nova Scotia,” making it the largest free Black community in North America, which is why the “Birchtown Muster of Free Blacks” exists. Adding to this, these new Black refugees in London and Canada had a hard time, with some of those in London resettled in Sierra Leone in a community which survived, and later those from Canada, with church congregations emigrating, “providing a strong institutional basis for the struggling African settlement.” After the war, 2,000 white Loyalists, 5,000 enslaved Blacks, and 200 free Blacks left for Jamaica, including 28 Black Pioneers who “received half-pay pensions from the British government.” As for the Bahamas, 4,200 enslaved Blacks and 1,750 Whites from southern states came into the county, leading to tightening of the Bahamian slave code.
As one historian put, “we will never have precise figures on the numbers of white and black Loyalists who left America as a result of the Revolution…[with most of their individual stories are lost to history [and] some information is available from pension applications, petitions, and other records” but one thing is clear “the modern history of Canada, the Bahamas, and Sierra Leone would be greatly different had the Loyalists not arrived in the 1780s and 1790s.” This was the result of, as Gary Nash, the “greatest slave rebellion of North American slavery” and that the “high-toned rhetoric of natural rights and moral rectitude” accompanying the Revolutionary War only had a “limited power to hearten the hearts of American slave masters.” 
While there are varied resources available on free Blacks from the narratives of enslaved people catalogued and searchable by the Library of Virginia, databases assembled by the New England Historic Genealogical Society or resources listed by the Virginia Historical Society, few pertain to the specific group this article focuses on. Perhaps the DAR’s PDF on the subject, the Names in Index to Surry County Virginia Register of Free Negroes, and the United Empire Loyalists Association of Canada (UELAC) have certain resources.
While this does not tell the entire story of those Black families who had left the colonies, stopping in Annapolis on the way, in hopes of having a better life, it does provide an opening to look more into the history of Birchtown, (also see here) and other communities in Canada and elsewhere. 
 Grumbelly was related to Capt. Keelings (of Princess Ann/Anne County, VA), x of whose people in bondage ran away to join the British lines” Argyll (joined Roal Artillery Department) and Robert. Grumbelly is also within this book. It would make sense it is Virginia’s Eastern Shore rather than Maryland’s, although this cannot be confirmed. William was undoubtedly one of many who was part of a small plantation within this area.
 Other would be evacuated on the La Aigle. His bio says that “William Keeling is assumed to be the husband of Pindar Keeling. They travel near to each other on board the Clinton and despite the presence of other Keelings, they are not listed in the Birchtown Muster.” Perhaps they settled in a different area or died on the voyage North. Pindar was formerly bound to a Norfolk slaveowner named Willis Ball. One transcript of the manifest says “William Keeling, 40, feeble fellow. Formerly the property of Grumbelly Keeling of the East Shore, Virginia; left him 6 years ago. GBC.” This being the case, then it makes sense that he cannot be found in Maryland records. It also clarifies that on 31 July 1783 the Clinton was Clinton bound for Annapolis [Royal, Nova Scotia] & St. John’s [Saint John, New Brunswick]. This means it was going to Nova Scotia ultimately. The GHOTES Genealogy and History of the Eastern Shore group on Facebook lists 38 enslaved blacks who had left New York, originally enslaved in the Eastern Shore (presumably Virginia’s).
 The word “loyalist” is used in quoation marks as it is an inexact term, and like Patriot it was used positively by those supporting the British Crown. Instead, the term supporter of the British Crown or any of its derivatives is used instead.
 Alan Taylor, American Revolutions: A Continental History, 1750-1804 (New York: W.W. Norton & Company, 2016), 21-22; A. Leon Higginbotham, Jr., In the Matter of Color: Race & The American Legal Process: the Colonial Period(New York: Oxford University Press, 1980), 91-95, 98-99
 Specifically referring to Abbaco (John Rootes, Benjamin Guy), and unknown location (Solomon Slaughter, William Causins, Francis Wright, John Morris, Thomas Fisher. Here the locations of those included in the above chart: Norfolk, Virginia (John Hirst, Matthew Godfrey, Robert Gilmore, Samuel Bush [Boush], John Willoughby, David McClaurin, William Mallery, William Egerson, James Hunter, Edward Hack Moseley [Mozely], Joseph Mitchell, Thomas Newton Snr, Robert Barns, Charles Connor, Samuel Elliot, Simon Hogwood, William Hancock, Archibald Campbell or Arthur Campbell., Thomas Hoggart/Hogwood, Mr. Scarborough, Stephen Tankard, William Hogwood/Hopgood Sr.); Nansemond, Virginia (Mills Wilkinson, Henry Burgess, Solomon Sheppard, Willis Wilkinson); Crane Island, Virginia (William Connor, George Robertson, Andrew Stewart [Stuart]); Portsmouth, Virginia (Willis Wilson, Andrew Sproule, Richard Brown); South Carolina (Captain Hullet, Bland Steward); Princess Anne/Ann County, Virginia (Edward Moseley, John Loveat); Pennsylvania (James Stewart); Mecklenburgh, Virginia (Richard Sweepston); Dismal Swamp (James Wright Moore); Petersburg, Virginia (John Holloway); Tanners Creek, Virginia (Anthony Walker [Walke]); Isle of Wight (Richard Jordan, Andrew Mckay); Suffolk, Virginia (Lambert Reddick); Greatbridge, Virginia (Alexander Foreman).
 The ten children born free were: Jonny, Patty, John Ceasor, Peter, Robert, George, Harry, Jonathan, Sally Nelis, and Agnes Reddick. The 16 born enslaved were: Sam, Ned, Lettius, Mary, Prudence, Edward, Valentine, Nanny, Judy, Joseph Reddick, Elsey Reddick, Joseph, Jenny, Andrew, Phebe,and Dempse.
 The “likely wench[s]” were Phillis, Seelah, Kitty, and Phillis Gordon. The “ordinary wench[s]” were Pleasant, Betsey, Molly (incurably lame of left arm), and Rose Wright. The “stout wench[s]” were Esther, Dorothy Bush, Mary Perth, Hannah Flemming, Fanny Brown (“Stout Lump of a Wench“), Wynce Gordon, Jane Halladay, Barbara Hancock, Peggy (“stout wench with 3 children 8, 5 and 4 months”), Rachel, Tilla Mosley, Patty Mosley (“stout wench,with child 2months“), Dinah Mitchell (“Stout healthy Negres with child in her arms. Left Charlestown from whence she was ordered by Dr. Humphry of the York Volunteers. then the property of Mitchel”), Jane Nelis, Nancy, Tamar Stewart (“stout wench, 3 small children“), Peggy Richards, Judith Johnson, and Dolly Wilkinson (“stout wench on her own bottom“). Patience was called a “likely girl,” Nancy Howard was called a “neat wench,” Chloe Johnson was called a “fine girl,” Nancy Sparrow was called a “feeble wench” and Mary Steel was called a “fine wench.”
 Gary Nash, Red, White & Black: The Peoples of Early North America (Upper Saddle River, NJ: Prentice Hall, 2000, Fourth Edtion), 276. On pages 274-279, Nash focuses on Black “Loyalists,” while on pages 280-284 he focuses on Blacks who stayed in America.
 The Nova Scotia archives has varied results when one searches for “Birchtown.”