Stephen W. Bennett

Stephen Wesley Bennett, age 75 of Dover, Delaware, went to be with the Lord on September 11, 2025 at Delaware Hospice in Milford, Delaware with his loving family by his side. He was born on April 4, 1950 in Milford, Delaware son of the late Jeanette Isaacs Bennett and Hammond Carey Bennett. He was also preceded in death by his sister Joanne Bennett.

Stephen, known to most as “Steve”, had many life accomplishments. Steve grew up in Milford, Delaware, where he spent his early years helping on the family farm. A graduate of Milford High School, he went on to earn a degree in computer science from Delaware Technical Community College. After college, Steve worked for the State of Delaware for several years before returning to his roots, joining his father on the family farm. Following his father’s passing, Steve continued the farming legacy alongside his son, Keith, where they raised chickens and cultivated the land. In 1980, Steve became a well-respected entrepreneur when he purchased the Dairy Queen in Milford, which he proudly owned and operated for 41 years. Known throughout the community as a dedicated and successful businessman, Steve also ran American Heritage Homes in the 1990s, where he designed and built custom homes. After retiring in 2020, he enjoyed spending much of his time at his home in Florida, reflecting on a life filled with hard work, family, and lasting contributions to his community.

Steve was known by all who knew him for his unwavering kindness, strong work ethic, and deep-rooted family values. He took great pride in his work, but his greatest joy came from spending time with his family. He was a loving husband, father, grandfather, and friend to many. In his spare time, he enjoyed the occasional round of golf and was an avid football fan, rarely missing a game. One of his favorite pastimes was traveling the country in his RV with his beloved wife, Barbara, creating cherished memories and exploring new places together. Steve’s life was a testament to the values he held dear—hard work, love of family, and treating others with warmth and respect.

He is survived by his beloved wife, Barbara Bennett, his daughter, Kathy Bennett, his sons, Keith Bennett (Shannon) and David Bennett (Tommie), his step children Cheri Hadley (Mike) and Bob Kolasinski (Cheryl); his brother Richard Bennett of California; his grandchildren, Kally Bennett, Seth Walsen, Alex Bennett, Charlotte Bennett, Alexa Dibble (Noah), Taylor Bennett, Elizabeth Baroni, Michael Prather, Emily Prather, and Samantha Gratteri; his three great grandchildren; many extended family members and friends.

A viewing will be held on Wednesday, September 17, 2025 where friends may visit from 6:00 pm to 8:00 pm at Berry Short Funeral Home, 119 SW Front Street, Milford, DE 19963. On Thursday, September 18, 2025 a viewing will be held at 12:00pm, funeral services will follow at 1:00 pm, followed by a grave side service and a potluck dinner at the Slaughter Neck Community Church, 23221 Argos Corner Rd, Milford, DE 19963.

In lieu of flowers donations can be made to the Slaughter Neck Cemetery.