Doris Mae Cleveland, a long-time resident of West Chop, died at Windemere on June 7 with family by her side. She was 99.

Born on December 15, 1924 at the Martha’s Vineyard Hospital in Oak Bluffs, Doris was the daughter of Herbert Raymond “Pat” Cleveland and Jane Jackson Cleveland of West Chop. She was a granddaughter of Captain and Mrs. Levi Jackson of Edgartown. Captain Jackson received a Carnegie Medal for heroism for saving the Captain and crew of the Mertie B. Crowley, which sank off Wasque, Edgartown, on January 23, 1910.

She attended school in Tisbury and graduated from Tisbury High School class of 1942. After high school, she was a homemaker, having married Clarence N. Ward Jr.in 1942. She had three children: Clarence, Carole and Herbert Ward. She divorced Clarence in 1956.

As a single mother of three children, she found work as a housekeeper for Mr. & Mrs. Paul Warburg, Mr. & Mrs. John Wilbur, Mrs. Ruth Morris, Mr. & Mrs. Justice Lowe and several other West Chop seasonal families. She was later employed by Ida Levine for the Vineyard Dry Goods Store. She also became a property caretaker for several summer families.

In 1959, she married Henry Oliver Perry of Oak Bluffs. They purchased a house on State Road, Vineyard Haven at the current location of Autoeuropa. She was a member of the Queenames Council, Degree of Pocahontas, as Wenonah, Pocahontas, and was the pianist. She was a member of Celestial Chapter #72, Order of Eastern Star, as organist, Worthy Matron, and Deputy Grand Matron of Grand Chapter of Massachusetts Eastern Star.

Besides her love for music, she was also artistically talented. She decorated pottery, crocheted, knit and made hooked rugs. Some of her hooked rugs won blue ribbons at the Agricultural Fair.

She divorced Henry Perry in 1965. In 1968, Doris married for the third time to George Maury, chief engineer for the Steamship Authority. They enjoyed digging for old bottles and using a metal detector on the Island beaches. They traveled by car several times to California, where he had a daughter from a previous marriage. They also traveled to Florida, where he worked on the engines for newer vessels for the Steamship Authority and would then sail them up to their new port in Vineyard Haven. They divorced in 1981.

She changed her last name back to Cleveland and moved in with her parents on Pine Tree Lane, taking care of them until her father died in 1981 and her mother in 1983. The house was left to her and she lived there until January 2023, when she moved to Windemere.

She is survived by her daughter, Carole Ward Maveety and her son, Herbert R. Ward both of Vineyard Haven; her four grandchildren Melinda Maveety, Kimberly Maveety Lefebvre, Robert C. Ward and Michael Ward; four great-grandchildren Kristina Ward, Allyssa Maveety, David Millen, and Ethan Lefebvre; and two great-great grandchildren Brycen Millen and Morningstarr Millen. She was predeceased by her son, Clarence N. Ward, III in 1993; her sister Violet M. Waters in 2014; and by her great-grandson Jason Millen in 2023.

A graveside service will be held on Saturday, June 22 at 1 p.m. at the Cleveland family plot at 376 Palm Avenue, Oak Grove Cemetery in Vineyard Haven. In lieu of flowers, donations may be made to any Island charity.

For online guestbook and more information please visit chapmanfuneral.com