WAY BACK WHEN: Fred Shepherd

Longtime Oakland resident Fred Shepherd was born in Winter Garden, and his wife’s family settled in West Orange County in 1919.

Fred and Sue Shepherd were married for 61 years, eloping in 1949 at the age of 19.
Fred and Sue Shepherd were married for 61 years, eloping in 1949 at the age of 19.
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Editor’s note: Way Back When is a new feature that records and preserves the stories and memories of lifelong West Orange and Southwest Orange residents.

Fred Shepherd has gone through life with very little change — he has lived almost all of his 93 years in West Orange County; he celebrated 61 years of marriage to his wife, the late Sue Tucker; and he enjoyed a 35-year career with the Florida Department of Corrections. One thing has changed, though, and that’s the Winter Garden and Oakland he knew as a child and young adult.

Born at his family’s home near downtown Winter Garden in 1931, he lived in the city for most of his childhood.

“I know I was born at home, because I didn’t have a birth certificate,” Shepherd said. “My brother was 19 months younger than I was, and he had a birth certificate, so I knew he was born in Orlando.”

His family moved in with his grandmother on North Dillard Street when he was 7, and he attended Winter Garden Elementary School. The following year, his parents bought a house on South Boyd Street, and he lived there until he got married.

As a child growing up in Winter Garden in the 1930s and ’40s, there wasn’t much to do. He was involved in Boy Scout Troop 46 — meeting in the basement of the old City Hall — and he was close to obtaining his Eagle rank when the scoutmaster quit and the troop dissolved.

Fred Shepherd still lives in the home he and his wife Sue built in Oakland in 1964.

He and his friends put his scouting skills to the test by camping around Lake Butler in the Kelso area and building a canoe.

“Well, it wasn’t exactly a canoe,” Shepherd said. “It was a boat, but it was covered with canvas. … and then you take paraffin and melt it down, and then you paint the paraffin, and it won’t leak on you.”

Shepherd and Tucker graduated from Lakeview High School in 1948, and he earned a degree in economics and education from the University of Florida.

“Then I got brave enough at night when I was 51, and I went back to college, and I’ve got a master’s degree in criminal justice from Rollins College,” he said.

After marrying the girl he met in the ninth grade at Lakeview High — they eloped when they were 19 — Shepherd moved a few miles down the road to her hometown of Oakland. They set up their first home near Johns Lake and lived there for about 13 years. They then bought property and built another house on East Henschen Avenue in 1965, and they lived and raised their two sons there.

Fred and Sue Shepherd, photographed at their son's wedding, were married for 61 years, eloping in 1949 at the age of 19.

Tucker died in 2009; Shepherd lives there still today.

He briefly left West Orange County in 1952 and joined the United States Army — playing clarinet in the military band — but after just two years, he received an honorable discharge and returned home when his wife told him she would never leave Oakland. The day of his discharge, he packed his car and drove from Alabama to Florida, arriving just in time for the birth of his first of two sons.


In the 1950s, Oakland had a popular hardware store, Gulley Hardware.

“They had rental lawn mowers, and they were electric, and the yard we had out on Johns Lake was easy to take care of, so I’d come up here and rent a lawn mower and cut it and then take it back,” Shepherd said.

He also remembers there were three grocery stores in the town: one owned by his father-in-law, Charles Mann “Pete” Tucker; another owned by Cecil Dees, near the four-way stop at Tubb Street and Oakland Avenue; and a third known simply as Elmer’s, owned by J.S. Redding and operated by a man named Elmer who drove a black Model A Ford and didn’t want anyone touching it.

Fred Shepherd's father-in-law, Pete Tucker, owned a small grocery store in west Oakland.

Tucker’s store, opened in 1930, sold meats and other groceries plus gasoline and kerosene. It was located on Oakland Avenue west of Tubb Street in the same block as the Tucker family home. Pete Tucker attended Tildenville Elementary School as a child and later became a cattleman, leasing and then later purchasing about 300 acres of land for a ranch west of Winter Garden. The land today is known as Tucker Ranch.

Pete Tucker was elected constable in 1933 and ran the store until he was elected justice of the peace in 1949. The C.M. “Pete” Tucker Square at the downtown roundabout is named for him.

Near the square is the Historic Town Hall, which once served as Oakland’s bank. Shepherd’s father-in-law told him once he had saved up $133, which he deposited into the bank.

“And then the bank went to hell and back, and everyone lost their money,” Shepherd said.


Shepherd spent 17 years on the street as a probation and parole officer with the Florida Department of Corrections. As he rose through the department’s ranks, he took on more responsibility, spending 18 years in administration.

“In that kind of work, I came to the conclusion that you can help those who want help, and there are those who are going to get back into trouble and they have to be removed and go to jail or prison,” Shepherd said.

The Oakland resident has been involved with Oakland Presbyterian Church since 1950 and serves the ministry in various ways.

He also keeps his eye on the town of Oakland and looks for ways to assist his community. When the town’s administration was being questioned for ethics in the early 1990s, Shepherd was asked to lead an investigation. He said after conducting basically an audit of the town, the committee determined the allegations were true but there wasn’t enough evidence to show criminal intent.

Shepherd also volunteered for about three years with the Winter Garden Heritage Foundation.

“I’ve always done these little things that I didn’t want any publicity over it, no thanks for it,” he said.


Shepherd has some ideas about the town’s future growth.

“If I was going to develop it, I would go to the highway property, and I would put in a medium-sized hotel, nothing elaborate, but nothing shabby; it would be up to snuff, so to speak,” Shepherd said. “Once you’ve got a nice hotel established, then I would establish several good restaurants. … The traffic patterns indicate they would support a small hotel and a couple nice restaurants. As far as restaurants are concerned, I like Bonefish.”



Amy Quesinberry

Community Editor Amy Quesinberry was born at the old West Orange Memorial Hospital and raised in Winter Garden. Aside from earning her journalism degree from the University of Georgia, she hasn’t strayed too far from her hometown and her three-mile bubble. She grew up reading The Winter Garden Times and knew in the eighth grade she wanted to write for her community newspaper. She has been part of the writing and editing team since 1990.

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