In Memoriam – Ray Middleton

Raymond Phillip Middleton (67) was taken from this life, his loving wife Jennie, family, and friends much too early by a tragic traffic accident in Savannah on June 19, 2026.

Ray was a third generation St. Simons Islander, the grandson of Mighty Fine Cowart and Lilly Cowart of Glynn Haven, the son of Dan and Valoryn Middleton, and youngest brother to Mike, Diane and Glenna. Ray was born in Waycross, Georgia but moved to St. Simons Island when only six months old. Ray grew up in Glynn Haven at the Middleton home on the marsh at the end of Cedar Street.

Ray attended St. Simons Elementary School, Glynn Middle School and was a 1978 graduate of Glynn Academy High School.

Ray obtained his Associate Degree from Brunswick Junior College and his Bachelor’s Degree in Business from Georgia State University. After graduating from Georgia State, Ray began training as a stock broker and intended to stay in Atlanta, but after a while in the big city, he moved back to St. Simons because he loved knowing everybody on the Island.

He was the quintessential big fish in a small pond because of his wonderful personality. When he came back to the Island, he trained briefly as an optician while going back to work at Poor Steve’s. After Poor Steve’s closed, in 1999 Ray and Brian Bell opened Marsh Point Bar & Grill where they were a local institution for many.

A bachelor until 48, Ray fell in love and married Jennie Gibbs to make her Mrs. Middleton. They were married among friends on July 7, 2007 in Las Vegas by Elvis. Jennie referred to Ray as “her Jewel”!

They brought their bachelor pets Marnier the lab and Sunny and Suzi the Boston Terriers into their home together. Ray and Jennie later adopted and loved Jelly Bean and Birdie the dachshunds and Fritz the cat. Ray and Jennie had almost 19 years together as soulmates.

Ray decided that after 30+ years as a bartender he wanted to retire from the fatigue of the late night routine and turned the reigns of Marsh Point over solely to friend and co-owner Brian Bell. Ray and Jennie decided to start limousine service Seaside Transport which they have owned for 14 years.

After marrying, Ray and Jennie adventured off the island because at the time they felt it was becoming too crowded. They tried St. Marys and Darien for a couple years each before they realized the saying, “When your toes hit the sand of The Golden Isles, it will always be home!” They returned to St. Simons Island.

Ray was a sports fanatic. He loved the Georgia Bulldawgs and was equally passionate about the Atlanta Braves. As a young boy he followed the Green Bay Packers and remained a life long fan.

Ray was a salt of the earth guy who was a genuinely pleasant person to be around. He found good in everybody he met and he was loved by all. From his childhood growing up on the Island, through his time as a bartender at Chances R, Poor Steve’s, and Marsh Point, to his ownership of Seaside Transport, Ray met so many people and had true friends among hard working blue collar folks and some of the most affluent folks of Glynn County alike. When Ray entered a room, it brightened from his presence.

Ray’s untimely passing has caused shock and pain to the community of St. Simons Island and he will truly be missed. Many were better persons for having known Ray.

There will be a Celebration of Life for Ray from 3pm to 6pm this Sunday, October 25 at American Legion Post 166 at Gascoigne Bluff on St. Simons Island. All who knew and loved Ray are invited to attend.