Cover photo for Ja'Len Woolford's Obituary
Ja'Len Woolford Profile Photo
2005 Ja'Len 2021

Ja'Len Woolford

March 1, 2005 — November 18, 2021

Ja’Len Sho’id Kheon Woolford, 16, entered eternal rest on Thursday, November 18, 2021. “J.A.”, as he was affectionately known, was born March 1, 2005 to DeQuane Wycha Woolford and Willie James Jackson, Jr., in Cambridge, Maryland.

Ja’Len was educated in the Dorchester County Public School  System. Ja’Len was a Junior at Cambridge-South Dorchester High School and would have graduated with the Class of 2023.

At an early age, Ja’Len participated in various sports for Dorchester County Recreation and Parks including, but not limited to, Basketball and Football. As he grew older, Ja’Len loved going Paintballing, playing PlayStation 4 and dining out at McDonalds, Taco Bell, and Chick-fil-A.

Ja’Len was a loving individual that enjoyed spending time with his close and loving family, but especially with his cousins, Flamond Woolford, Jr. and Loden Burris.

Ja’Len was preceded in death by his parents, DeQuane Woolford and Willie Jackson, Jr.; his maternal grandfather Wayne “Ricky” Demby, Sr.; his paternal grandparents Willie Jackson, Sr. and Mamie Hall-Jackson.

Among those left to cherish his memory are his grandmother, Joyce Banks (Randall); great grandmother, Gloria Woolford; sisters, Tiffany Andrews (Matthew), Kashya Jackson, Tiana   Gordon-Jackson, Kaymee York and Alasia Perry; brother, Willie Jackson, III; three aunts, Pastor Marlene Hamlin,  Lesley Jackson and Kasandra Jackson-McMillion (Larry); four uncles, Flamond Woolford, Sr., Wayne Demby, Jr., TaVon Young(Jalessa) and Gary Bryan, Jr.; twelve great aunts, JoAnn, Lois and Sandra Woolford, Bonnie Young Sampson, Angela and Christine Young, Joyette Wilson, Delores, Elsie, Fostine, Arletha and Patricia Demby; five great uncles, Larry and Douglas Nichols, Rudolph (Cynthia) and Kevin (Darlene) Woolford and Lester Demby(Jessica); great-great aunt, Rosetta Montgomery; great-great uncle, Louis Woolford; godmothers, Janetta Skinner and April Lewis; godfathers, Paul Baiers and Joseph Lewis; five nieces, two nephews and a host of cousins and close friends.

To order memorial trees or send flowers to the family in memory of Ja'Len Woolford, please visit our flower store.

Service Schedule

Past Services

Public Viewing

Saturday, December 4, 2021

10:30am - 12:30pm

Waugh Chapel United Methodist Church

425 High St, Cambridge, MD 21613

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Celebration of Life

Saturday, December 4, 2021

Starts at 12:30pm

Waugh Chapel United Methodist Church

425 High St, Cambridge, MD 21613

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Interment following funeral service

Old Field Road

TBA, TBA,

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