Stephen Wesley Bennett, 75, passed away on September 11, 2025, at Delaware Hospice in Milford.
Born the son of the late Jeanette Isaacs and Hammond Carey Bennett, Steve, as he was known, grew up in Milford on his family farm. He graduated from Milford High School and earned a degree in computer science from Delaware Technical and Community College. After graduation, he worked for the State of Delaware before returning to his roots, joining his father on the family farm.
After his father passed, Steve farmed with his son, Keith, raising chickens and cultivating the land. In 1980, Steve purchased the Dairy Queen in Milford, owning and operating the location for 41 years. A dedicated and successful businessman, Steve also operated American Heritage Homes in the 1990s, designing and building custom homes. Steve retired in 2020, spending much of his time at his home in Florida.
Steve had a strong work ethic and deep-rooted family values. Although he took great pride in his work, but his greatest joy was spending time with family. He was a loving husband, father, grandfather and friend. Steve enjoyed the occasional round of golf and was an avid football fan, rarely missing a game. He also enjoyed traveling the country in his RV with his wife, creating cherished memories and exploring new places. Steve’s life was a testament to the values he held dear – hard work, love of family, and treating others with warmth and respect.
“So sorry to hear of Steve’s passing,” John Rutt posted on his obituary. “It has been since Richard and I sat together on the school bus that I have been in contact with anyone in the family. My condolences to the family. May God give you peace and comfort.”
Others expressed similar sentiments.
“I am so saddened to hear of Steve’s passing,” Dee Betts Smith said. “Although we haven’t communicated in many years, I remember well what a dear, kind person Steve was when we were young. Soft spoken, easy going, gentle spirit, kindhearted, a man whose friendship I hold in my heart.”
Steve is survived by his beloved wife, Barbara; daughter Kathy Bennett; sons Keith (Shannon) Bennett and David (Tommie) Bennett; his stepchildren, Cheri (Mike)Hadley and Bob (Cheryl) Kolasinksi; his brother, Richard Bennett of California; his grandchildren, Kally Bennett, Seth Walsen, Alex Bennett, Charlotte Bennett, Alexa (Noah) Dibble, Taylor Bennett, Elizabeth Baroni, Michael Prather, Emily Prather and Samantha Gratteri; three great-grandchildren and many extended family members and friends.
A viewing was held September 17 at Berry Short Funeral Home in Milford. A viewing and funeral service was held September 18 with graveside services and a potluck dinner at the Slaughter Neck Community Church in Argo’s Corner. In lieu of flowers, donations can be made to the Slaughter Neck Cemetery.
