Holland family tree logo Sussex County, Delaware The Hollands of Oysterrocks
Five Generations, One Record

Family Tree

The documented descendants of Cyrus Holland, drawn from the family's own genealogical register — and the key people and places in Lewes that carried his name forward.

This page follows two family documents: a formal genealogical register, "Descendants of Cyrus Holland," and a one-page family summary, "Key People and Places in the Holland Family History," together with its hand-marked map. Names, dates, and burial locations below are transcribed as the family recorded them. Where a birth or death date wasn't recorded, it's left blank rather than guessed at — and a few entries, especially from the 1800s, may never be fully resolved.

A note on names: family sources differ slightly on Cyrus's wife. Wendell F. Holland's written history names her Cotta Burton, which is the name used throughout this page; the genealogical register records her as Cottie (Cotta) Kegiah. Both point to the same person — the family may want to reconcile which surname is correct.

Key People

Who shaped the story at Oysterrocks

Key Places

Seven sites, marked by the family

  1. Uncle/Cousin Winnie's store — Theodore Winchester Holland's convenience store.
  2. Burton's Chapel and Holland Cemetery — became Holland property by marriage, through Jeremiah (2nd generation).
  3. Oyster Rocks and Holland Family Property — the farm and road that still carry the family name.
  4. Johnnie Walker and Lewes Beach — Johnnie Walker Beach, just east of Lewes Beach, was the designated beach for African American families during segregation.
  5. Shipcarpenter's Square and St. George's AME Church — the church sits on Park Avenue, across from Shipcarpenter's Square.
  6. "Grandmom's" House — 313 West 4th Street.
  7. Black Cemetery in uptown Lewes
Hand-marked map of key Holland family sites in Lewes, Delaware
The family's own annotated map of these seven sites, from "Key People and Places in the Holland Family History."

The Register

Descendants of Cyrus Holland

Generation 1

Cyrus Holland and his wife, and the children who carried the Holland name into the next generation.

Cyrus Holland
b. 1791, Delaware — d. 1881

Born into slavery; freed February 9, 1827 by Elizabeth Holland. Married Cotta Burton (b. 1800, Sussex County, Delaware — d. 1870). Bought his first 40 acres at Oyster Rocks in December 1845.

Children of Cyrus Holland and Cotta Burton:

  • Jacob W. Holland (1823–1884) — m. Cecelia Gumby
  • James Holland (b. 1827)
  • Hannah Holland (b. 1832)
  • Jeremiah Holland (1834–1913, Burtons Chapel AME Church Cemetery) — m. Ruth Emily Burton, 1858
  • Mary Holland (b. 1837, Sussex County, DE)
  • Ellenor Holland (b. 1840)
  • Ann E. Holland (1842–1915)
  • James H. Holland (b. 1845)
  • Elzey Eli Holland (b. 1829) — m. Elizabeth Holland

Generation 2

The two lines that carry through the rest of this record: Jacob W. Holland's family, and Elzey Eli Holland's family.

Jacob W. Holland
b. 1823, Georgetown, Sussex Co., DE — d. 31 Dec 1884, Georgetown, DE

Married Cecelia Gumby (b. 1827 — d. 26 Feb 1890).

  • Eliza Ella Holland Webster (b. 1843)
  • Jacob Wright Holland Jr. (1865–1918)
  • Hannah Holland Lewis (1863–1950) — m. James Lewis
  • Hettie Holland Polk (1854–1933, Philadelphia, PA)
  • Drucilla Ann Holland Young (b. 1857)
  • Mary Holland Tunnel (b. 1869)
  • Cecelia Holland (1861–1889) — m. Alfred Allen (d. Apr 1889, lost on the Enoch Turley)
  • Andrew Holland (1856–1932, Harrison Smith Cemetery)
  • Cyrus Holland (1859–1915, Eden Cemetery, Philadelphia) — m. Emma M. Williams
Elzey Eli Holland
b. 1829

Married Elizabeth Holland.

  • Mary L. Holland (b. 1863)
  • Cornelius Elzie Holland (b. 1864)
  • Rev. Jeremiah Holland (1861–1939, Burton's Chapel Cemetery) — m. Mary White, daughter of Daniel and Saddy White
  • George Edward Holland (1855–1907)
  • Jacob W. Holland (b. 1858)

Side branches recorded in the register: Hannah Holland Lewis and James Lewis's children — Drucilla, Reba May Lewis Wiltbank, Emma, Cressisus, and James M. Lewis. Cecelia Holland and Alfred Allen's child, recorded only as "Unknown Allen," was born 14 Feb 1882 in Lewes.

Generation 3

Jacob Wright Holland Jr.'s family, and Rev. Jeremiah Holland's family — including Theodore Winchester Holland, "Uncle/Cousin Winnie."

Jacob Wright Holland Jr.
b. 1865, Sussex Co., DE — d. 07 Aug 1918, New Castle, DE (Peoples Memorial Park)

Married Hannah Jane Heavelow (b. 06 Aug 1873, Lewes, DE — d. 31 Jan 1962), daughter of Juber Heavelow and Hannah J. Miller, in 1891.

  • Rosa Mae Holland (b. 03 Aug 1899) — m. Louis Edward Riley
  • Roy Eli Holland (1891–1975, Peoples Memorial Park) — m. Edith Elizabeth Willis
  • Jacob W. Holland III (1894–1920, Harrison Smith Cemetery)
Rev. Jeremiah Holland
b. 24 Jun 1861, Lewes, DE — d. 13 Oct 1939, Milton, DE (Burton's Chapel Cemetery)

Married Mary White (d. 25 Dec 1972, Burton's Chapel Cemetery), daughter of Daniel and Saddy White, in 1858.

  • Everett Holland (1887–1907, Burton's Chapel Cemetery)
  • Ulyssus Holland (b. 1888)
  • Theodore Winchester Holland, "Uncle/Cousin Winnie" (1890–1974, Burton's Chapel Cemetery) — m. Lillie Turner, 1910
  • Cyrus Holland (1895–1984)
  • Myra Bernice Holland (1899–1995, Burton's Chapel Cemetery)
  • Jeremiah William Holland (1904–1983) — m. Janie L. Foster, 1942

Generations 4 & 5

The great-grandchildren and great-great-grandchildren of Cyrus Holland — including the Riley line connected to the Lewes Historical Society's family history exhibit.

Rosa Mae Holland & Louis Edward Riley
Louis Edward Riley: b. 24 Sep 1893, Lewes, DE — d. 21 Jun 1937, Lewes, DE (Harrison Smith Cemetery)
  • Stillbirth Boy Riley (10 Apr 1922)
  • Louis Alfred Riley (12 Nov 1917 – 19 Nov 1917, Pilottown Cemetery)
  • Stillbirth Girl Riley (04 Aug 1916)
  • Stillbirth Girl Riley (07 Apr 1920, buried in the family's back yard)
  • Louis Edward Riley Jr. (b. 20 Jan 1938, Lewes, DE) — m. Lonnie Swanger; also recorded m. Ruth Greene
  • Rosa Jane Riley (1924–1946) — m. Paul Williams
  • Beatrice Ann Riley (1925–1977, Peoples Memorial Park) — m. George Marshall Showells
  • Emily E. Riley (b. 1935, Lewes, DE)

Louis Edward Riley Jr., born 1938, is very likely the same Lewis Riley whose 2022 oral history appears on the Oyster Legacy page — and the family chart on the Lewes Historical Society exhibit banner in the Gallery is titled for him by name.

Roy Eli Holland & Edith Elizabeth Willis
Roy Eli Holland: b. 26 Oct 1891, Lewes, DE — d. Oct 1975 (Peoples Memorial Park)
  • Emma Agustia Holland (1912–1913, Harrison Smith Cemetery)
  • Elaine Holland Ward (1916–2006, Owings, MD)
  • Elizabeth W. Holland Bullard (1922–2004, Owings, MD)
  • Jacob W. Holland IV (b. 1924)
  • Roy Eli Holland Jr. (1932–2004, Camden, NJ)
Jeremiah William Holland & Janie L. Foster
Jeremiah William Holland: b. 29 Jun 1904, Lewes, DE — d. Nov 1983
  • Bernice Holland (b. 29 Jun 1945, PA)
  • Jeremiah William Holland (b. 31 May 1949, PA)
  • Wendell Foster Holland (b. 10 Feb 1952, PA)

A portrait in the family archive is hand-labeled "Bernice Holland Moore" — possibly this same Bernice, later married. See it in the Gallery.

Sources: "Descendants of Cyrus Holland" and "Key People and Places in the Holland Family History," both from the family's Family History Notes; cross-referenced with "The Hollands of Oysterrocks" by Hon. Wendell F. Holland. This record isn't exhaustive — later generations and some side branches aren't yet included here.