Joshua Naylor (1751-1835)

A Stories250 Revolutionary War Ancestor's Story

Joshua Naylor (sometimes spelled Nailor) is my 5^th great-grandfather on my maternal-paternal side. His Revolutionary War service includes some of the most pivotal fights in the entire war.

Joshua was born in December 1751 in Frederick County, Maryland, the son of George Joshua Naylor and Margaret A. Wimsatt (later Woodward).¹ He was born at a pivotal time in American history. Maryland was both a prosperous colony and a contested frontier, exposed to raids during the French and Indian War. Over time, residents of the state became disillusioned with British rule. In 1765, when Joshua was 14 years of age, Maryland was one of the first colonies to repudiate the Stamp Act. In fact, a group of 12 judges in Frederick County, Joshua’s home county, led the repudiation of the act.²

Frederick County, MD, circa 1750-1775. Map created using ChatGPT.

As Joshua grew into manhood, revolutionary fervor grew steadily. On 10 February 1776, at the age of 24, Joshua enlisted as a private in the 7th Company of the First Maryland Regiment.³ His service would place him in some of the most crucial campaigns of the Revolutionary War.

Joshua’s regiment gained lasting renown at the Battle of Brooklyn (Long Island), 27 August 1776. Vastly outnumbered by British and Hessian forces, the Marylanders launched repeated counterattacks, sacrificing themselves to protect the Continental Army’s retreat. Of roughly 260 men who charged, more than two-thirds were killed or captured. Washington later praised their valor, stating, “Good God! What brave fellows I must this day lose!” History remembers them as the “Maryland 400.”⁴ Joshua was present for this defining moment, and though his individual role is not detailed, his service links him to this legendary stand.

During the Battle of Brooklyn, the First Maryland Regiment lost approximately one third of their total troop strength. Casualties were substantially higher in the Third, Fourth, Sixth, Seventh Independent, and Ninth Companies who were forced to make a last stand at Old Stone House. Some of these companies lost over eighty percent of their men.⁵

Map showing troop locations during the Battle of Brooklyn. Map ©Maryland State Archives (https://msamaryland400.com/battle-of-brooklyn-map1/)

After the Battle of Brooklyn, the Maryland soldiers regrouped and marched North on Manhattan Island. Joshua’s regiment fought at Harlem Heights (16 September 1776), a small but morale-restoring skirmish where the Americans repelled the British in northern Manhattan.⁶ He was also at the Battle of White Plains (28 October 1776), where Washington’s forces endured another retreat but survived to fight on.⁷

In December, the Maryland troops joined Washington in the audacious crossing of the Delaware River (25–26 December 1776). Despite bitter cold and icy waters, the army crossed successfully and defeated the Hessian garrison at Trenton the next morning.⁸ Days later, at Princeton (3 January 1777), they secured another victory.⁹ These twin successes revived the Revolution at its lowest ebb.

Washington Crossing the Delaware, by Emanuel Leutze, 1851, Metropolitan Museum

After four years of service, Joshua was discharged from the 4th Maryland Regiment on 20 May 1780.¹⁰ He had survived the Revolution’s darkest days and participated in its most iconic campaigns.

Joshua married Martha Nutwell in Prince George’s County, Maryland, on 17 January 1780.¹¹ Their first known child, John Naylor, was born on 20 December 1786 near Georgetown, Maryland.¹²

Martha died sometime after 1790. Census records from that period indicate Joshua lived in Prince George’s County, Maryland, with four males under the age or 15 and one female of indeterminate age, assumed to be Martha, but by 1792 he was a widower.¹³

On 11 June 1792, Joshua remarried. His second wife, Morning Stoggins, bore him several children as they established their family in Montgomery County, North Carolina.¹⁴

Their known children include:

• · John Naylor (1786–1855), son of Martha Nutwell

• ^· George Naylor (1801-1881)

• ^· Wade Hampton Naylor (1807-1857)

• ^· Nancy A. Naylor (1810-?)

• ^· Jamima Naylor (1811-)

• ^· Joshua Naylor, Jr. (1813-1868)

• ^· Leonard Naylor (1817-1850)

Joshua’s move to North Carolina reflected larger post-Revolution migration patterns. Veterans and their families often sought new opportunities in the South and West. North Carolina’s Piedmont was attractive for its fertile land, available through grants and bounty land warrants. Several members of Joshua’s extended family made the same migration including his cousin, Batson Naylor who settled in nearby Rowan County.¹⁵

Migration southward from Maryland and Virginia followed the Great Wagon Road, which stretched from Pennsylvania through the Shenandoah Valley into the Carolinas. Families like the Naylors traveled this route in search of farmland, community, and religious fellowship, often joining growing Methodist and Baptist congregations in their new homes.¹⁶

Joshua’s life after the Revolution was shaped by his status as a veteran. Many veterans faced economic struggles, as pensions were inconsistent and often delayed. In 1822, Joshua was awarded a pension for his Revolutionary War service.¹⁷ These grants provided some support in old age and recognized his contributions to independence.

Veterans like Joshua often became community pillars. They carried the memory of sacrifice and helped knit together the new nation’s civic and religious life. While some lived in poverty, the shared identity of service remained a point of pride.

Joshua lived to the remarkable age of 83, dying on 24 June 1835 in Montgomery County, North Carolina. He was buried at Lane Chapel Methodist Cemetery near New London, Montgomery County.¹⁸

Gravestone of Joshua Naylor at Lanes Chapel Church Cemetery, Montgomery County, NC. Photo by S. Cato (Find a Grave Contributor #48455312) https://www.findagrave.com/memorial/62066192/joshua-naylor/photo

His life trajectory reflects the experiences of his generation: originating as a British colonial subject, shaped by participation in the independence movement, and subsequently becoming a pioneer in new territories. His children and grandchildren carried the Naylor name into the 19th century and beyond, extending his legacy in the South.

Joshua Naylor’s story is one of resilience and renewal. From the desperate stand of the Maryland 400 to the bitter cold of Valley Forge, and from the promise of new land in North Carolina to the peace of his final years, his life traced the trajectory of the early United States.

He embodied the Revolution’s promise: an ordinary man who, through service and sacrifice, helped secure liberty for generations to come.

1. Most genealogies of Joshua Naylor point to George Joshua Naylor and Margaret Woodward as his parents. One profile, from the Archives of Maryland biographical series, lists his parents as Samuel and Mary Naylor. It does not provide any documentation to back up that assertion.

2. Gaines, Danielle E., “Stamp repudiation left its mark on Frederick, country,” The Frederick [Maryland] News-Post, 14 November 2015, (https://www.fredericknewspost.com/news/politics_and_government/stamp-repudiation-left-its-mark-on-frederick-country/article_127bd1a4-39fe-5c6f-b520-cf772759cd94.html).

3. Revolutionary War Military Records, Maryland Archives, enlistment roll, 10 February 1776, 7th Company, First Maryland Regiment.

4. “Read the Revolution, Washington’s Immortals,” Museum of the American Revolution: 31 August 2016; review of Washington’s Immortals, by Patrick O’Donnell, (https://www.amrevmuseum.org/read-the-revolution/washington-s-immortals).

5. Tacyn, Mark Andrew, “’ To the End:’ The First Maryland Regiment and the American Revolution” (PhD diss., University of Maryland College Park, 1999), abstract.

6. Schenawolf, Harry, “Battle of Harlem Heights Sept. 16, 1776: Americans Gave the British a Good Drubbing,” Revolutionary War Journal: 15 January 2014, (https://revolutionarywarjournal.com/battle-of-harlem-heights/).

7. “The Battle of White Plains,” Finding the Maryland 400, Maryland State Archives: 28 October 2013, (https://msamaryland400.com/2013/10/28/the-battle-of-white-plains/).

8. “The Crossing and the Capture,” Finding the Maryland 400, Maryland State Archives: 26 December 2013, (https://msamaryland400.com/2013/12/26/the-crossing-and-the-capture/).

9. “A Fine Fox Chase: The Battle of Princeton,” Finding the Maryland 400, Maryland State Archives: 3 January 2014, (https://msamaryland400.com/2014/01/03/a-fine-fox-chase-the-battle-of-princeton/).

10. Joshua Nailor (Pvt., Maryland Line, 4^th Regiment, Col. Hall’s Company, U.S. Revolutionary War), pension no. S. 41,914; Case Files of Pension and Bounty-Land Warrant Applications Based on Revolutionary War Service, compiled ca. 1800 - ca. 1912, documenting the period ca. 1775 - ca. 1900; U.S. Revolutionary War Pension Files; Record Group 15: National Archives, Washington, D.C. imaged: Fold3, (https://www.fold3.com/image/25085915/nailor-joshua-page-6-us-revolutionary-war-pensions-1800-1900), accessed 20 September, 2025.

11. Maryland Records Colonial, Revolutionary, County and Church from Original Sources Marriage Licenses Issued at Upper Marlborough, Prince George's County, Maryland--1777 to 1801.* Maryland Records Colonial, Revolutionary, County and Church from Original Sources Marriage Licenses Issued at Upper Marlborough, Prince George's County, Maryland--1777 to 1801.* Name: Joshua Naylor Spouse: Martha Nutwell Marriage Date: 17 Jan 1781.

12. ''1850 Census'': "United States, Census, 1850," database with images, (FamilySearch Record|MCDQ-PZ3): accessed 21 September 2025 FamilySearch Image S3HY-DC6Q-LWP ''John Nailer (63) in Bedford, Bedford, Tennessee, United States. Born in Maryland.'' citing Affiliate Name: The U.S. National Archives and Records Administration (NARA); Affiliate Publication Number: M432; Line: 10; Digital film/folder number: 004191095_002_M9C4-YBF; FHL microfilm: 24560; Image number: 87; Record number: 10226; Packet letter: A; Indexing batch: N01133-0. [John’s birth date seems to be family lore. I have not been able to confirm it, other than the probable year based on census records.]

13. Martha Nutwell Naylor’s death date is estimated based on a female of her age appearing in the household on the 1790 Census and Joshua’s apparent marriage to Morning Stoggins Harril in 1792, although that date is questionable, see note 14.

14. There are some questions as to the date of the marriage of Joshua Naylor and Morning Stoggins Harril. In her sworn statement supporting her widow’s pension request, she stated that they were married on 11 June 1792.

"United States records," images, FamilySearch (https://www.familysearch.org/ark:/61903/3:1:3QSQ-G9F9-S9SL?view=fullText : Sep 6, 2025), image 378 of 940; United States National Archives and Records Administration. Image Group Number: 007584784.

But an abstract of marriage licenses in Rutherford County, NC, shows the date as 10 September 1799.

Ancestry.com. Rutherford County, North Carolina, U.S., Marriages, 1779-1868 [database on-line]. Lehi, UT, USA: Ancestry.com Operations, Inc., 2013. This collection was indexed by Ancestry World Archives Project contributors.

Original data: Holcomb, Brent H. Marriages of Rutherford County, North Carolina, 1779–1868. Baltimore, MD: Genealogical Publishing Co., 1986.

This is important because the law granting pensions to widows required that they be married prior to 1794.

15. 1810 U.S. census, Rowan County, North Carolina, page 287 (penned), line 3, Batson Nailer; imaged, “1810 United States Federal Census,” Ancestry (https://www.ancestry.com/search/collections/7613/records/778448?tid=203657777&pid=312709410003&ssrc=pt/: accessed 22 September 2025).

16. Robert W. Ramsey, Carolina Cradle: Settlement of the Northwest Carolina Frontier, 1747–1762 (University of North Carolina Press, 1964), 10-22; imaged, Internet Archive (https://archive.org/details/carolinacradlese0000rams/: accessed 22 September 2025).

17. “U.S., Revolutionary War Pensioners, 1801-1815, 1818-1872,” database with images, Ancestry (https://www.ancestry.com/search/collections/1116/records/122538 : accessed 22 September 2025), entry for Joshua Nailor of North Carolina.

18. Find a Grave, database and images (https://www.findagrave.com/memorial/62066192/joshua-naylor: accessed September 22, 2025), memorial page for CPL Joshua Naylor (Dec 1751–24 Jun 1835), Find a Grave Memorial ID 62066192, citing Lanes Chapel Church Cemetery, Montgomery County, North Carolina, USA; Maintained by Beverly, Sharon & John,Jr (contributor 47169632), with tombstone images by Dorothy Wilkie (contributor 47323722).