Sherry (Bobbitt) Bailey, 75, of Browns, Illinois, passed away Tuesday, January 6, 2026, at Deaconess Midtown Hospital in Evansville, Indiana, surrounded by her loving family. She was born on October 27, 1950, in Mount. Carmel, Illinois, the daughter of Lewis Bobbitt and Vivian Ellen Mastaw. She married William F. Bailey on June 18, 1988, and together they enjoyed twenty-nine years of marriage until his death on May 29, 2018.
Sherry was an exceptional cook whose heart for others was evident in everything she did. Known for her kindness and generosity, she was always ready to help those in need. She used her cooking talents and organizational skills to raise funds and support members of her community during difficult times. Everyone knew that if there was a need, Sherry was the one to contact for help and support. She joined the VFW Women’s Auxiliary and remained a member for twenty plus years. For a time, she was the District President. Sherry had a passion for giving and honoring which is evident in all that she did for her community and the Veterans. She was active in the Memorial Day services every year and was an important part in organizing Toys for Tots, Easter Egg Hunts and Trunk or Treat. She was in charge of bingo nights at the VFW which raised funds for the Veterans. Sherry was even found calling the bingo numbers from time to time and made it a fun event. On weeks that she made her famous fried chicken and dressing dinners, it brought in an even bigger crowd at the “V”. Memories of Sherry will be treasured by her family and friends for years to come and her presence on this earth and in her community will be dearly missed.
Sherry leaves behind her son, William Major Bailey (Sara Schmittler); four grandchildren, Chrissy (Carlos) Barradas, Rachel (Jaise) Dunn, Brittany (Landon) Fewekes, Kaeli Reynolds; eleven great-grandchildren, Mario, Gabriella, Kya, Jackson, Luka, Jameson, Zoey, Taylor, Brinley, Kenna, and Beau; Brothers, Mike (Tonya) Bobbitt, Eddie Bobbitt, Roger Bobbitt; sister, Myrna Moffitt; many loved nieces, nephews, great, great-great and great- great-great nieces and nephews. Sherry loved and treasured her whole big Bobbitt family.
Sherry was preceded in death by her parents; husband, Bill; son, James Edward (Jimmy) Reynolds; brothers Ronnie Smith, Steve Bobbitt; sisters, Brenda Schmitt, Judy Maass and sister-in-law, Shirley Bobbitt.
Family and friends are invited to gather for a Visitation from 11:00 a.m. to 1:00 p.m. Saturday, January 10, 2026, In the Chapel of Keepes Funeral Home.
Funeral Services will be at 1:00 p.m. Saturday January 10, 2026, in the Chapel of Keepes Funeral Home.
Memorial contributions may be made in Sherry’s memory to Keepes Funeral Home to help her family offset the expenses. Envelopes will be at the funeral home or can be mailed to Keepes Funeral Home, 1500 North Cherry Street, Mount Carmel, IL 62863.
