Dianna Lynn Stilwell

Dianna Lynn Stilwell, 77, of Winchester, passed away on Monday, August 18, 2025, at IU Health Ball Memorial Hospital in Muncie.

Dianna was born on April 29, 1948, in Winchester to the late Russell and Lola Simmons. She was a 1966 graduate of Driver High School and went on to earn her associates degree in Child Development from Ivy Tech. Dianna was owner and operator of Dianna’s Tots to Teens Home Daycare and Nursery School and Ragedy Ann and Andy Daycare. She had also worked for Hoosier Park, Walmart, Arbor Clinics, and had spent several years traveling the state working in child advocacy. Dianna served as a Girl Scout Troop Leader and YMCA Volunteer.

Dianna attended Winchester First Church of the Nazarene and Main Street Christian Church. She was involved in Singles Interaction, and Euchre Clubs at Muncie and New Castle Senior Centers. Dianna enjoyed watching her children and grandchildren play sports, listening to country music, playing cards and Bingo, and watching the Young and the Restless.

Dianna is survived by three children, Michael Stilwell (wife Carrie), Cindy Stilwell, and Kyle Stilwell (wife Amanda); four grandchildren, Jake Stilwell (wife Anna), Zach Stilwell (wife Delaney), Lauren Stilwell, and Kylee Stilwell; a great-grandson, Thomas Stilwell; a brother, Richard Simmons; and several nieces and nephews.

Dianna was preceded in death by her husband of 46 years, Michael Stilwell. A funeral service to celebrate Dianna’s life will be held at 11:00 am Friday, August 22, 2025, at Walker Funeral Home. Pastor Ken Rickett will officiate. Burial will follow in Fountain Park Cemetery. Friends and family may gather to share and remember from 6:30 pm until 8:30 pm on Thursday, August 21, 2025, and also one hour prior to the funeral on Friday at Walker Funeral Home.

Memorial contributions may be given to the American Cancer Society, PO Box 6704, Hagerstown, MD 21741.

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