Dorothea "Dolly" Winston

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Dorothea "Dolly" Winston (Dandridge)

Nicknames: "Dorothea Spotswood (Dandridge) Henry Winston"
Birthdate:
Birthplace: Chelsea, Hanover, Virginia
Death: Died in Halifax, Virginia
Place of Burial: Red Hill Plantation, Charlotte Co., Virginia
Immediate Family:

Daughter of Nathaniel West Dandridge, Colonel and Dorothea Dandridge
Wife of Patrick Henry, Sr. and Judge Edmund Winston
Mother of Dorothea Spotswood Winston; Kitty Henry; Alexander Spotswood Henry, Sr.; Edward Winston Henry, Sr.; John Henry, of Red Hill and 2 others
Sister of Col William Dandridge; Martha Payne; Nancy "Ann" Redd; Alexander Spotswood Dandridge; Nathaniel West Dandridge II and 6 others

Managed by: Private User
Last Updated:

About Dorothea "Dolly" Winston (Dandridge)

Dorothea Spotswood Dandridge (1755 - 1831)


In her obituary, DOROTHEA SPOTSWOOD DANDRIDGE HENRY WINSTON was acclaimed to be “of the ancient Dandridge family.” Yes, she was of this “ancient family,” but more than that, she lived in one of the most important eras of United States history and was “up to the task” as the expression goes!

Dorothea was born, 25 September 1757, to Nathaniel West Dandridge and his wife, Dorothea Spotswood in Hanover County, VA. Spending her early life on a thriving plantation, she had frequent contact with the “movers and shakers” of the growing rebellion against English tyranny. Indeed, she and George Washington’s, wife Martha Dandridge Custis were cousins.

On 9 October 1777, Dorothea married Patrick Henry in Hanover County, VA as his second wife. During his Leatherwood years and his Red Hill years, Patrick Henry, his wife, and children lived in a frontier environment. This may be difficult for those of us who live in this same territory today to imagine. It was in this pioneer atmosphere with the added dangers of war that Dorothea raised her family, including HER VERY OWN AUTHENTIC DAUGHTERS OF THE AMERICAN REVOLUTION.

After Henry’s death, Dorothea married, as his second wife, Judge Edmund Winston of Hanover County, VA. Judge Winston died in 1818, and Dorothea spent time visiting with her children. It was at the home of one of her daughters, Sarah B. Scott, in Halifax County, VA, that Dorothea died 16 February 1831. She is buried at “Red Hill, Charlotte County, VA beside Patrick Henry.

With their marriage in 1777, the new Mrs. Henry became the first First Lady of the Commonwealth of Virginia and moved into the Governor's Mansion in Williamsburg. Shortly after Henry left this term of office as governor, the couple and their growing family moved to his Henry County plantation, "Leatherwood." To the young Dorothea, this was a culture shock because the Henry County territory was a frontier wilderness compared to what she had previously been accustomed. One can imagine her relief when Henry again became governor and moved his still growing family to Richmond, the new capital. Now her "real" daughters of the American Revolution could find more eligible suitors.

Following this stint as governor, Henry moved to "Red Hill” and renewed his law practice to recoup the fortunes of both his wife and himself, fortunes which they had spent in support of Washington's army during the Revolutionary War. By the time he died in 1799, Dorothea had borne him eleven children. Henry's will stipulated that his widow was to receive nothing if she remarried; but after struggling for three years to care for the underage children and to manage the various plantations Henry had acquired through the years, Dorothea married Judge Edmund Winston and moved her family to his home near Lynchburg. This action resulted in lawsuits and counter suits over Patrick Henry's property, a legal hassle that outlasted Dorothea.

When her second husband died in 1818, the 63-year-old Dorothea found herself with all of Henry's seventeen children grown up and either married or away at college. She then moved to live with her daughter and son-in-law, Sarah and Alexander Scott at their plantation, "Seven Islands" in Halifax County, VA. Here she died on 14 February 1831, in her 74th year. At her request, her children buried her at "Red Hill," next to her beloved first husband, Patrick.

In her role as First Lady of Virginia in both Williamsburg and Richmond, she entertained the great statesmen of the day. In her role as wife and patriot, she provided Patrick Henry the freedom to fulfill his role as one of the nation's founding fathers by relieving him the worry of his home and family while he was often away.

From her obituary in the Lynchburg Virginian (15 August 1831, page 3), one reads, "married... in the midst of the Revolutionary War, [Dorothea Dandridge Henry Winston] participated largely in those toils and perils to which the extraordinary part [Patrick Henry] acted in those days exposed him. ... When... his fellow citizens elevated him to the first gubernatorial chair of Virginia under the new government, this estimable and venerable lady enjoyed with him the honors of this trust; and... [when] he felt compelled to resign his office and remove to the frontier of Virginia to repair a broken fortune, she never failed to cheer and animate that great man in providing for his numerous family. Every man who has tasted the sweets of the conjugal state well knows the important duties which devolve on the wife, and it may be truly affirmed that no woman ever acted her part with more sincerity and cheerfulness."

-------------------- Info added per DAR's "Lineage Book of the Charter Members" by Mary S Lockwood and published 1895

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Dorothea "Dolly" Winston's Timeline

1757
September 25, 1757
Chelsea, Hanover, Virginia
1777
October 25, 1777
Age 20
1778
August 2, 1778
Age 20
1781
November 3, 1781
Age 24
Leatherwood, Henry, Virginia, United States
1785
October 9, 1785
Age 28
Henrico, VA, USA
1788
June 2, 1788
Age 30
Prince Edward, Virginia, United States
1790
April 7, 1790
Age 32
Pleasant Grove, Virginia
1794
January 21, 1794
Age 36
Long Island, Virginia
1796
February 16, 1796
Age 38
Charlotte , Virginia
1831
February 14, 1831
Age 73
Halifax, Virginia