Carole Pennington Webster passed away gracefully in her Nantucket home on March 9, 2024. She was born in Stover, Mississippi to Lucille Melton Pennington and Harvey Thomas Pennington on January 30, 1943, and was raised with her brothers Benny, Johnny, and Harvey, Jr. In high school, Carole was on the track team and a cheerleader. Talented and beautiful, Carole was named Miss Tallahatchie in 1961. She adored her parents, and until her last days, spoke of her love for her mother.

Carole met David in Mississippi and they married in 1967. Soon thereafter, they moved to Nantucket. For 56 years, they spent every day together. Together, they launched Webster & Associates, an early real estate firm on the island. Carole’s passion for The Magnolia State was rivaled only by her love of Nantucket. She and David shared a great love of travel, but especially of Florida and Paris.

They both often mention that they feel there is no finer place to live than Nantucket Island. Carole and David loved dining out and through the years have spent many happy hours and meals at two of their favorite restaurants, The Opera House and Le Languedoc. A longtime member of the Nantucket Yacht Club, they enjoyed friends, events and regular meals, and achieved 50-year member status!

Carole and David had a close group of friends, many of whom were Nantucket artists and designers. Visiting with friends was one of her favorite activities. Back in the day, she and David loved to go dancing at 30 Acres. One evening, the band Mountain was playing, and the electricity went out. The only musician who was able to continue playing was drummer Corky Laing, who made up a song on the spot as he watched Carole dance with her friend Roy Bailey, and called it Mississippi Queen, a song which hit the charts in 1970.

Carole and David were part of a group of ladies and gents who spent time at the beach near Bartlett’s, coining the term “Ladies Beach”. Always up for a fun event, Carole and David created the “NBBBS, the Nantucket Backgammon, Beach, and Bubbly Society” complete with printed scorecards, bangle bracelets for the regulars, and monogrammed towels.

Carole is pre-deceased by her stepson, Christopher Webster, and survived by her stepson, David (Chip) Webster and his wife Sara Boyce, her granddaughter Macy Alexandra Webster Ramirez, her cousin Cathy Burgess, and her loving husband David, an 18th generation Nantucketer who considers himself lucky to have spent his life with Carole.

A private service will be held at the Folger Plot of the Prospect Hill Nantucket Cemetery.