Maxine Regina Stanley

Maxine Regina Stanley was a loving mother, grandmother, great grandmother and great great grandmother. She was born April 13, 1935, the second child of the late Earl and Mildred Y. Stanley. She departed this life on Monday February 10, 2025, at Tidal Health Center in Salisbury, MD after a brief battle with heart disease.

Maxine loved the Lord and her family. She was a kind and gentle soul who helped people through her kindness and thought nothing of it. She started her walk in Christ at an early age. During her early years, Maxine and her parents were members of Waters U.M. Church Fork Neck Road in Vienna, MD. Maxine later joined Waugh Chapel U.M. Church. While a member of Waugh, she was an active member of the church Finance Committee, Waugh Gospel Choir, Food Pantry, SPPRC, Ushers’ Board, Weekly Soup Committee, and Kitchen Committee. Her love of the Lord and Family kept Maxine busy supporting Waugh UMC, and her mother’s church Mt. Pleasant UMC. This faithfulness included supporting the church family days, breakfast and dinner fundraisers, and all the other events sponsored by her church. However, her favorite event was “Stanley Day,” where she loved seeing family from near and far to worship together.

Maxine had a diverse work history and demonstrated dedication and experience across multiple industries. Her strong work ethic and commitment to service are evident throughout their career journey. She worked in the Bogash Sewing Factory and Rob Roy Manufacturing. She retired in 2000 from the State of Maryland, where she worked in the Dietary Department at the Eastern Shore Hospital Center and later with the Vocational Rehabilitation division, assisting individuals in developing skills and finding meaningful employment.

Maxine committed to her community by engaging in various civic activities, demonstrating a strong commitment to community service and social justice. As a member of the Dorchester County Election Board, she contributed to the democratic process by ensuring fair and efficient elections. Her involvement with the Red Cross highlights her dedication to humanitarian efforts, providing aid and support to those in need. As part of the NAACP, she advocated for civil rights and equality.

Maxine joined the Progressive of Dorchester Temple #224, where she was a member for over 15 years, serving as a Trustee, member of the Bessie Leonard/Ethel K. Jews Council, Past State President Council, National Past Grand Daughter Ruler’s Council, and the Eastern Shore Past Grand Daughter Ruler’s Council.

Maxine embodied a dynamic and multifaceted personality marked by strength, independence, and unwavering love for her family. As a strong and fierce individual, she approached life with resilience and determination. Maxine’s outspoken nature ensured her voice was heard, as she advocated for herself and those she loved. As the family matriarch, she held the family together with wisdom and leadership, guiding those around her with strength and compassion.

Maxine loved to play Pinochle. She brought laughter, skills and strategies to the table. She truly enjoyed the thrill of competition. The games sometimes lasted 10 hours in one day. Maxine loved cooking, entertaining and most of all traveling. She said she loved to travel and took every opportunity to “travel the world”.

Maxine had six children. She was married to James Chester who passed away in 1987; Maxine married Norman Stanley and gained 2 daughters and 1 son.

She leaves to cherish her memory daughter, Diane Allen (New Jersey), stepdaughters Michelle (Christopher) Scott, Janice Stanley-Milton both from Phoenix Arizona; sons Jerome Stanley (Victoria), Anthony Stanley (Towanna), James Chester (Sharon), Byron Chester and stepson Byron Pinder of Baltimore, MD. She was a loving grandmother to fifteen (15) grandchildren, thirty-one (31) great grandchildren, and five (5) great great grandchildren. She is also survived by one sister, Arjorie Chandler; three brothers Shelton Stanley, Carlton Stanley, and Arnette Stanley; brother-in-law Randolph (Nona) Stanley; and a host of nieces, nephews, cousins and friends.

She was preceded in death by her beloved husband, Norman Stanley; her daughter, Shanel Chester; her brother, Ralph Young; and her sister, Delphine Lee.