Milford- Dennis Whitmore, 77, passed away peacefully on May 3rd, 2026 surrounded by his wife and family. He was born on August 30, 1948 in West Old Town to Damon and Rita Whitmore. Dennis spent his early years on the family’s farm and then moving between Old Town and Milford before settling in Milford where he and Roxanne raised their family.

At 20 years of age, Dennis was drafted to the Army and volunteered to serve his country in the Vietnam War. During his time in the service, he earned his Expert Rifle Marksmanship Badge, a Vietnam Campaign Medal, a Vietnam Service Medal as well as a National Defense Service Medal, an award for honorable active service during designated national emergency periods. A proud veteran all his life, Dennis was rarely seen without his “Vietnam Veteran” hat. Though he did not speak of his service often, he took comfort in talking to and hearing the stories of his fellow veterans.

Dennis spent the majority of his working career at the City of Old Town, Public Works Department. At Public Works, Dennis operated heavy machinery, most notably a heavy loader and the street sweeper. Dennis made many life long friends at the Public Works and retired from there after 26 years.

Dennis had a deep love for the outdoors. He spent countless hours outside four-wheeling, hunting, fishing, and camping with his family. Many cherished memories were made camping at Deer Lake, including one unforgettable trip when a hurricane flooded their tent, leaving his son Ryan’s sleeping mat completely soaked. In his later years, Dennis and Roxanne enjoyed spending time in their camper at Forest Ridge Campground with Reggie and Wanda.

Dennis also had a passion for cooking and was well known for his “Chili Feeds” and spaghetti dinners, which he enjoyed sharing with friends, family and his coworkers from the City of Old Town. His granddaughter Ruby fondly recalled that he made the “best beans”.

Dennis enjoyed simple pleasures such as playing Parcheesi, lifting weights and relaxing on the porch while people-watching. A proud Vietnam Veteran, he loved his country and demonstrated that pride as a lifetime member of AMVETS. Over the last year, he took great comfort in praying at night with his niece, Stephanie.

If you have ever been to Dennis and Roxanne’s house, you would know that he was a fan of Westerns. He loved to watch John Wayne classics, Bonanza and Gunsmoke and would sometimes put on a Southern accent for fun. When Dennis was not watching Westerns, he could be found cheering on the New England Patriots.

Above all, Dennis treasured his family. He shared nearly 55 years of marriage with his beloved wife, Roxanne, and together they built a life filled with love and devotion. He was deeply proud of his sons, DJ and Ryan, and cherished the many hunting and brook fishing trips they shared. His grandchildren, whom he lovingly called his “Little Buddies,” held a special place in his heart. He created lasting memories with them, from chasing them around the house to taking them “fishing” in backyard puddles.

Dennis will be remembered for his natural sense of humor, his honesty, and his genuine nature. He had a way of making people laugh without even trying and was never afraid to speak his mind.

He was predeceased by his parents, Damon and Rita Whitmore; his siblings Emily, Earl “Jr.”, Richard, and Roger; his in-laws Reginald and Rita Sanborn; and two of his closest friends, Bill Walker and Bill Walton.

He is survived by his wife, Roxanne; his sons, DJ and his wife Becky, and Ryan and his wife Tianna; his beloved “Little Buddies,” Kiaira, Ruby, and Ian; his siblings Allen, Amelia, Carol, and Brian. A graveside service will be held on Friday, May 15, at 11:00 a.m. at the Milford Cemetery. Family and friends are invited to attend and celebrate Dennis’s life. Following the graveside service there will be a gathering at the family’s house on the Call Road in Milford.

In lieu of flowers, please consider making a donation to House in the Woods, a non-profit retreat center in Lee, Maine, that offers free, outdoor self-help programs for U.S. Military Veterans, active-duty personnel, and their families.