Shayla Lee Gregory was born on June 24, 1987 in Plymouth, Massachusetts, where she grew up. Her birth was highlighted in Jet magazine. She passed away on December 2, 2015 at the age of 28.

Shayla was known for her exuberant and creative spirit. As a young girl, she developed a flair for fashion that lasted her entire life. She also enjoyed dancing and music. A high point of her youth was when she saw her beloved *NSYNC in concert and met the band backstage.

Shayla's love of travel began with childhood trips to Disney World, and she often planned all aspects of family vacations. Later she would earn college credit for a study abroad program in Greece.

Shayla's passion for business also emerged at a young age. As a teen she received numerous regional and national awards for competitions held by DECA, a student business association dedicated to preparing future leaders in management, marketing, and hospitality. She was a cheerleader at Plymouth North High School and graduated in June 2005.

Shayla's combined interests in travel, entertainment, and business led her to choose a program in Sports/Entertainment/Event Management at Johnson and Wales University, which she began while finishing her last year of high school. She studied at the Providence, Rhode Island and Charlotte, North Carolina campuses and graduated cum laude with a Bachelor of Science degree in May 2008.

As the first grandchild and niece of the Gregory family, Shayla – affectionately known as Shay Bear – was everyone's baby. Her affectionate and engaging personality drew family members home for the holidays, which provided the opportunity to share her hopes and dreams for the future. Her family last saw her during the Thanksgiving holiday. Recently, Shayla spent her time in Lawrence, Massachusetts with her best friend and boyfriend, John Bickford.

Shayla is survived by her mother and stepfather Paula and Roger Cenac, her father Gary Heyward, her siblings Julian, Olivia, and Joshua Cenac and RJ Deshields, her grandparents Lillian and Dick Gregory and Isaiah Heyward, and countless aunts, uncles, and cousins.

The wake will be held from 5 pm to 7 pm on Tuesday, December 8 at Bartlett Funeral Home, 338 Court St, Plymouth, MA. The funeral service will be held from 11 am to 2 pm on Wednesday, December 9 at Hotel 1620 (formerly the Radisson), 180 Water Street, Plymouth, to be followed by the burial.