IN LOVING MEMORY OF

Sheila

Sheila Lolly Profile Photo

Lolly

d. Jul 30, 2025

Obituary

With quiet grace and deep peace, Sheila Maria Lolly transitioned from her earthly life to her heavenly home on July 30, 2025. Her radiant spirit, vibrant soul, and unwavering devotion to those she loved left an indelible mark on everyone fortunate enough to know her.

Sheila was born with a gift—not just of beauty and strength, but of passion. Educated through the Caroline County Public School System, she quickly learned that her heart would be her compass. Every endeavor she pursued stemmed from love: whether she was inspiring fitness clients at American Family Fitness, creating confidence through her artistry as a makeup artist for MAC Cosmetics, or pouring every ounce of her joy and energy into raising her beloved son, Emilio.

She was more than a mother—Sheila was Emilio's fiercest advocate, his unwavering ally, and his daily dose of sunshine. The bond they shared was extraordinary—a testament to a heart that loved deeply and gave generously.

Sheila's life was also marked by enduring relationships. On August 19, 1995, she married James Scott, a union that evolved into a lifelong friendship built on mutual respect and care. On October 2, 2004, she married the love of her life Timothy Lolly. Together, they were gifted with their greatest blessing: their son, Emilio.

She was preceded in death by her grandparents, Brosia Upshaw and Richard Lewis, whose legacy of strength and perseverance lived on through Sheila. Also preceding her in death were her uncles James Upshaw and Elwood "Woody" Williams and cousins Dion Tyler and Ricky Williams.

Left to celebrate her memory are her devoted husband, Timothy and cherished son, Emilio; her mother, Mary Upshur, whose love shaped her; her sisters, Lisa (Elmer) and Kim (Jared); nieces, and nephew, Kennedy, Khloe, Jade and Gabriel; her nephew-son, Christopher; and sister-cousin, Ramona White and dearest friends, Stacy Lewis and Leah McClure and a wide circle of cousins and friends whose lives were touched by Sheila's warmth.

To know Sheila was to be embraced by love. Her smile could light up a room, her loyalty was unwavering, and her compassion ran deep. She lived with authenticity, never chasing trends—only truth. Her legacy will live in every heart she held, every life she lifted, and every moment she made magical.

Rest well, beautiful soul. You were—and always will be—loved with our whole hearts.

A viewing will be held at A.L. Bennett and Son Funeral Home, 200 Butternut Drive, Fredericksburg, VA, 22408, on Friday, August 8, 2025, at 1:30 PM followed by a funeral service at 2:30 PM. The interment will be held privately.

To send flowers with our preferred florist or plant a memorial tree, please visit our flower store.

Funeral Services

Viewing

August
8

Friday

A.L. Bennett and Son Funeral Home

200 Butternut Drive, Fredericksburg, VA 22408

1:30 - 2:30 pm

Funeral Service

August
8

Friday

A.L. Bennett and Son Funeral Home

200 Butternut Drive, Fredericksburg, VA 22408

Starts at 2:30 pm

Guestbook

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