Lolita Aileen Hollenbeck, age 63, passed away peacefully on April 29, 2026, in Springfield, Massachusetts. Born on April 27, 1963, in Trenton, New Jersey, Lolita was the beloved daughter of Voncell (Grinstead) Jackson and Hilliard Jackson. Lolita grew up in Springfield Massachusetts. She attended Catholic schools for her early education. She moved to Northern California with her family and graduated from Crystal Springs High School. She continued her academic journey at Davis University, and Tufts University, where she pursued studies in creative writing and pre medical studies. In 1989, Lolita proudly joined the United States Army, where she honorably served her country and rose to the rank of Specialist. During her military service, she met her beloved husband, the late David Clarence Hollenbeck Jr. Her dedication and bravery earned her the National Defense Service Medal, the Southwest Asia Service Medal, and two Bronze Stars for her courageous participation during Operation Desert Storm. Lolita was a woman of tremendous faith, compassion, and warmth. She loved creative writing and poetry, and she had a joyful spirit that was reflected in her love of laughter and appreciation for a good joke. A proud Veteran, she deeply valued the opportunity to serve her country. Above all else, she devoted her life to serving the Lord wholeheartedly. She faithfully volunteered her time and talents at St. Michael's Cathedral and Dr. Elouise Franklin, New Hope Church of God and Christ where she was a cherished member of her church community. Lolita leaves to cherish her memory her beloved son, David Clarence Hollenbeck III, along with a host of loving cousins, extended family members. Her legacy of service. love. faith, and laughter will remain in the hearts of all who knew and loved her. A chapel service will be held on Wednesday, May 27, 2026 at 2pm at the Massachusetts Veterans Memorial Cemetery, 1390 Main Street, Agawam.