Obituary: Richard “Dick” Ayres Waldroup

Richard “Dick” Waldroup, 77, Dies After 13‑Year Battle With Prostate Cancer

Portland, Maine — Richard “Dick” Ayres Waldroup, a longtime community member and former Army veteran, died peacefully at his home on September 5, 2026, surrounded by his wife of 38 years and family. He was 77.

Waldroup was born in Winchester, Massachusetts, on May 5, 1949, to the late John Curtis and Albertina Vivian (Silva) Waldroup. He graduated from Reading High School and went on to earn a degree from Northeastern University. After college, he served in the United States Army with the 173rd Airborne Brigade in Vietnam, where he received a Bronze Star for his service. He later continued his military career with the Army National Guard for several years.

Following his military service, Waldroup joined the United States Postal Service. He began as a letter carrier in Wakefield, Massachusetts, before moving to Portland, Maine, where he worked for 30 years. He rose to the position of Safety and Injury Compensation Manager before retiring. After retiring, he kept himself active by driving a school bus in Yarmouth and working as an usher for the Portland Sea Dogs baseball team.

“Richard was a man who loved to keep moving,” said a friend of the family. “Whether it was the bus route, the baseball game, or the golf course, he was always ready to lend a hand.”

Waldroup’s private life was equally full. He and his wife, Stephanie (McCarthy) Waldroup, were married in 1988 and remained together until his passing. They raised two sons: Michael R., who lives with his wife Julie (Lernihan), and Matthew J., who lives with his wife Kelly (Fisher). The family also includes four grandchildren—Evelyn, Amelia, Maren, and Eloise—who survived him.

He battled prostate cancer for 13 years, beginning in 2013, but remained active and engaged with his family and friends throughout the fight. Waldroup was known for his enthusiasm for golf, and he enjoyed cheering for the Boston Red Sox and the New England Patriots. In the winter months, he was a “snowbird,” spending time in Florida.

Waldroup predeceased his parents, sister Jill, and sister Pamela (Waldroup) Sarno. He also leaves behind a brother, Jack Waldroup, and numerous close friends.

A viewing will be held at Lindquist Funeral Home, 1 Mayberry Lane, Yarmouth, from 10:30 a.m. to 12:00 p.m. on Friday, September 11. A memorial service with military honors will follow at 12:00 p.m., with a reception to follow. Those wishing to leave messages may sign an online guest book on the Lindquist Funeral Home website.

The Waldroup family would like to thank the community for its support and for the many kind messages received during this difficult time.