Dorothy Ann Oliver, age 76, of Huntingtown, passed away on January 24, 2026. Born in 1949, she was the daughter of Walter Ray Cubbage and Josephine (Wightman) Cubbage.

Dorothy was born in Prince Frederick and grew up in Mount Rainier, Maryland. She moved to Owings in 1976 and later settled in the Neeld Estate neighborhood of Huntingtown, where she became a deeply involved and beloved member of the community.

She had a 25-year career as a hairdresser in Aspen Hill and later ran a family business in Clinton, Maryland. In recent years, Dorothy owned and operated a well-established eBay business, creating and selling customized keepsakes.

Dorothy was a longtime member of Emmanuel United Methodist Church in Huntingtown. She was also an active volunteer and devoted supporter of the Beach Buccaneers Youth Club. She was instrumental in securing Kellam's Field and helping keep the Buccaneers organization in Chesapeake Beach. In recognition of her dedication and service, the Beach Buccaneers present The Dorothy Oliver Award each year to a cheerleader who exemplifies high standards both on and off the field.

Within her Neeld Estate community, Dorothy played a central role in shaping the neighborhood. Rarely seen without a camera, she captured countless moments and milestones for family and neighbors alike. She also created and maintained the community website and was especially instrumental in organizing the annual Fourth of July parade and celebrations—traditions that reflected her love of community and her gift for bringing people together year after year.

Above all, Dorothy was a devoted mother and an extraordinary grandmother. She was a constant presence in her children's and grandchildren's lives and their most enthusiastic supporter. To those who knew her, she embodied everything one could hope for in a mother and grandmother.

Dorothy also participated in the Senior Olympics, earning medals in several events. She enjoyed gardening and was an original Washington Capitals season ticket holder, often taking neighborhood children to games and practices. Her greatest joy came from being with family and contributing to the lives of others.

Dorothy is survived by her children: Michael Oliver (Jodi) of DeBary, Florida; Steven Oliver (Suzanne) of Ormond Beach, Florida; and Amy Cronin (Matt King) of St. Johns, Florida; her grandchildren, Kaleigh, Connor, Dylan, and Deegan; and her partner of 25 years, Brent Golden.

She was preceded in death by her parents and her brother, Walter "Buddy" Cubbage.

Family and friends are invited to attend a funeral service on Saturday, February 14, 2026, at 12:00 p.m. at Emmanuel United Methodist Church, 1250 Emmanuel Church Road, Huntingtown, MD 20639.

Dorothy will be deeply missed and lovingly remembered for the lasting difference she made in her family, her community, and the lives of so many young people.

In lieu of flowers, the family invites those wishing to honor Dorothy's memory to make a Venmo donation to the Neeld Estates Community Association, reflecting her lifelong commitment to serving others. Venmo @Dorothy_Neeld_Memorial_Fund