Geraldine Malinda Benson Gaile affectionately known as “Sis” departed this life on Monday, February 9, 2026, at the age of 92. She was born in Cottage Grove, Westover, Maryland on December 25, 1933, to the late Burley and Louise Fitchett Benson of Westover.
After graduating from the Somerset County Public School System, she worked in retail at Read Drugs, Rite Aid Pharmacy, Ames Department store which she retired from for the first time. After a short retirement she decided to return to the workforce at the Shoe Department in Fruitland where she retired again at the age of 83 years old.
Geraldine was a member of the John Wesley United Methodist Church at Cottage Grove, in Westover. She loved her church family.
She leaves to cherish her memories: one daughter, Louise D. Gaile (John); one very devoted niece, Kathy Grant Beckett (John); three great nieces, Cornita Price, Shatiesha Collins and Nia Cottman, all of Princess Anne; five great nephew, Darrell and Reginald Collins, Oluranti Fallon and Dashee Covington; a host of special friends, Margaret Grant, Betty Clark, Yvette Northam, Shirley White, and Fontina Vickers; neighbors, Ernie, Steve and Yvonne Elmore.
In addition to her parents, she was preceded in death by two sons, Larry “Punkin” Gaile and Charles W. Gaile, a daughter, Winifred E. Gaile; one sister, Martha Fallon, two brothers, Charles V. Benson and Burley Benson; two nieces, Shelia Collins and Francis A. Fallon Covington Henry.
A funeral service will be held 12 noon Wednesday, February 18, 2026, at Anthony E. Ward, Jr. Funeral Home in Princess Anne with a viewing one-hour prior. Visitation and viewing will also be held 6:00 PM-8:00 PM Tuesday, February 17, 2026, at the Funeral Home.
Interment will follow at John Wesley (Cottage Grove) Cemetery in Westover.
29 Responses
I will always remember her having to send me home. I was just like one of her kids and her kids were like my mom’s kids. We were pretty much inseparable during high school years. This really touches my heart sadly. She’s one of the last of the village! Rest well in Gods perfect peace.
Remembering Ms Gerald as good friend’s with my mom and cousins Betty Anne and Granny SIP and my God bless your daughter she is in my prayers
One of my favorite cousin s My heart is heavy but I have a ton of Precious Memories -To Baby Sis
Your Mom is with the Heavenly Host of. Angels
That’s in Heaven to Welcome Her
God has another Angel
RIP My Dear Cousin and
Friend 🙏🙏🙏❤️
My condolences 🙏🙏
Extending My Deepest Condolences and Prayers
I will miss my cuz..nice Lady
Prayers 🙏 and my deepest heartfelt 💔 condolences to the family
Sending condolences to the family, very sweet lady.
My deepest sympathy and Condolences and Prayers to Baby Sis and family the last one from the family of Greenwood neighborhood. Much Love ❤️
Very well thought of and very respected lady. God bless and. Condolence to family
A very well respected lady fun to be around her always friendly Godbless condolence tofamily
To the the entire Gaile family I’m sorry for your loss of Geraldine and she was love and caring. I’m going to miss her so much. I will always remember her and her family. I’m sending my prayers and condolences to her entire family. May God gives you the strength for healing during this difficult time and difficult loss.
Prayers and my condolences to the Family.
Baby Sis
You have my deepest sympathy
Sending my deepest condolences to the family. Mrs. Gale was a wonderful child of God.
Sending my condolences to the family
Praying for the family. Keep holding on to the many sweet precious memories. I remember your mother’s smile and warm personality!
Sending my deep sympathy to you and your family
I would like to express my heartfelt sympathy to the family. . Sis was very special to me, one of my mother’s dearest friends. They are together in Heaven! May our Heavenly Father be a comforter and give you strength. God bless you family, I love you and I am praying for you. Love and prayers
I remember Mrs. Geraldine. She was our next door neighbor when we lived in Greenwood. My deepest sympathy.
2 Timothy 4:6-8. Rest In Eternal Peace, Aunt Sis. You will be missed.
We’re so sorry for the passing of Mrs Geraldine. She was one of my costumers for years until she stop driving. We will surely miss her in the neighborhood. Prayers and condolences to the family. My friend Rest in Heaven 💐
My condolences to the family for the lose of Ms. Geraldine. We worked together at Ames in Salisbury.
As Julia Hayward said, “she’s one of the last of the village.” Louise, I am so, so sorry for your loss. Mrs. Gaile was mommy to two of my dearest friends. Be strong. Love, Debbie
Baby Sis:
Cecelia and I are very sorry for your loss. We send our heart felt sympathy and condolences to you and John Boy. We have fond memories of the Christmas birthday celebrations, May she rest in peace with our God and Savior Jesus Christ.
Sending prayers for the family of Geraldine Gaile Had the opportunity and pleasure of working with her at Ames.
Louise,
So sorry to hear of your loss. Your mother was truly a nice person, always so pleasant, and a devoted member of John Wesley United Methodist Church, Cottage Grove. I will miss seeing her at church and please know her passing is a great loss to her John Wesley family.
Prayers going out to the Gaile family, sorry for your loss, I also worked worked with Gearldine at Ames.
🙏🏾🙏🏾🙏🏾