Ann Millicent Bailey

Mrs. Ann Millicent Bailey, 78, of Frederick, Maryland, passed peacefully at home going to be with the Lord Saturday, January 25th, 2025. She was the beloved wife of Charles “Beetle” Bailey, married for 55 years. 

Ann was born January 15, 1947 in Washington D.C. to Mr. and Mrs. Walter & Anna Wolff. One of eight children, she spent her childhood in North East D.C., graduating high school in 1964 from Northwestern High School. After graduating, Ann attended PG Community College followed by joining National Airlines as a stewardess. Ann had many adventures during her time in the airlines and loved regaling family and friends with stories from meeting the band Peter Paul and Mary to asking Tarzan actor Johnny Weissmuller to do his classic Tarzan yell. Out of the various destinations she visited, Spain remained one of her favorites. 

Through her love of tennis she met her husband Beetle, marrying in 1970, followed by a wonderful honeymoon in Oahu, HI. After living in Damascus for over a decade, they purchased land in the Catoctin Mountains building their dream house themselves, thus creating the cherished family home “Tha Pwopady” or The Bear House as it’s known to many Frederick County locals. There, Ann and Beetle raised their five beautiful children and built lifelong memories with their grandchildren, extended family, and dear friends. 

Ann had a deep, personal relationship with Jesus Christ and was an active member in the Church of the Redeemer. She participated in multiple bible studies over the years building lasting friendships through those groups. Ann was also a greeter at church, where she’d often greet folks with a classic Ann Bailey kiss. 

One of Ann’s life long dreams was to visit the filming locations of the movie Sound of Music since she had seen it 42 times in the theatre before graduating high school. She and Beetle made that come to fruition for their 40th wedding anniversary by taking the Sound of Music tour through Salzburg, Austria. It was a trip of a lifetime. 

Over the years the family enjoyed vacations at Capon Springs and Farms where they became 3rd week of August regulars. Decades of trips to Capon forged strong friendships and deep family traditions they hope to continue. 

Ann was preceded in death by her parents, brothers Eddie and Buddy Wolff, sister Lynn Thomas, and Granddaughter Reese Olivia Bailey. 

She is survived by her husband Charles Bailey of Frederick; sons Michael (Amanda) Bailey of Boonsboro; Christopher (Heather) Bailey of Keedysville; Patrick (Ashley) Bailey of Walkersville; Peter (Rebecca) Bailey of Frederick; and daughter Lauren (Brad) Hill of Woodsboro. Along with her loving grandchildren Samantha, Mikayla, Clark, Bryson, Marin, and London. Ann is also survived by Brothers Spencer, Danny, and Paul Wolff; sister Maggie Voorhees; Sister-in-law Mary Bessio; and many beloved nieces and nephews. 

The family will receive friends to celebrate the life of Ann M. Bailey at Stauffer Funeral Home, 1621 Opossumtown Pike, Frederick, MD 21702 on Saturday February 8th, 2025 from 1-5pm in a drop-in style setting. Prayers will be offered at 2pm.