History Hotspot: Mail-made Mary Esther


Did you know that Mary Esther has the oldest continuously operating post office between Pensacola and Apalachicola?

JENNIE McKEON @JennieMnwfdn

MARY ESTHER — You could say the City of Mary Esther was mail-made.

In 1871, an early settler, John Newton, established the region’s first post office. It is the oldest continuously operating post office between Pensacola and Apalachicola, and for years served as the only nearby mail stop.

But the city’s story goes back a bit further.

Getting settled

The first settler of Mary Esther was Jesse Rogers, who in 1842 moved his family and large cattle herd from what is now known as Niceville to Santa Rosa Sound, according to a 1988 article from the Okaloosa County Shopper. Around this time, only one other family was living in the area.

Some historical records say Rogers was the infamous pirate Billy Bowlegs. In his 1961 book, “History of the Playground Area”, author Leonard P. Hutchinson discredits the claim by stating, “Aside from the pertinent fact that Jesse Rogers was not of the cutlass-swinging, gold-plundering era, his physical build — bowlegged to a crippling extent and less than 5 feet tall — distorts the sea-rover picture into an absurdity.”

By the mid-1850s, Newton came to the area from the Euchee Valley (near DeFuniak Springs). Newton was an abolitionist, a Presbyterian minister and taught school until he was forced to resign for teaching from anti-slavery books. He opened the first school during the Civil War, which also doubled as a church, and then established the post office on Oct. 10, 1871, according to historical records from the Baker Block Museum website.

Since the community needed to have a name for mailing, he’s also credited with giving Mary Esther its name. There are three theories: Either Newton named the city after his wife, it’s a combination of his daughters’ names or a combination of his wife and daughters’ names. The location of the post office was likely inside his home. The mail was delivered by boat from Pensacola.

Legacies and ghost stories

The legacy of the Rogers family and the Pryor family is evident in Mary Esther’s history. The Pryor family continues to live on the same property purchased by the early settlers on the north band of Santa Rosa Sound. Not too far away from the Pryor homestead is the Jesse Rogers Memorial Cemetery.

Thomas Jefferson Pryor sailed to Mary Esther in the mid-1850s as a deckhand on a schooner headed for Pensacola. He met Ona Rogers, daughter of Jesse, and they were married in May 1879. Thomas started a lumber business, and Thomas and Ona had 10 children, two of which — Tom and Roger — served as mayors of the town.

Thomas was postmaster in 1899, and members of the Rogers family carried on the position until 1972.

The Pryor family operated the post office, using a corner of their grocery store, Pryor’s Grocery, on Highway 98 from 1915 to 1938. Tom Pryor was the postmaster until the grocery business picked up and his wife, Mary, took over the job from 1938 to 1972.

“It was an area about 10-feet wide,” Tom said of the makeshift post office in a 1982 Daily News story. “It was enclosed so the mail could be protected. The mail went through a cubbyhole.”

The post office outgrew the space and a small wooden building was built next to the grocery store.

When Alice Rogers and Charles Shipley married, Alice’s mother, Mary Watson Rogers, gave the newlyweds 6 acres of waterfront property where Alice and Charles built a summer boarding house in 1906. It was named “The Cedars” for the many cedar trees on the property. The property is now an apartment complex known by the same name.

According to a historical record kept at Mary Esther City Hall, guests were often entertained with the legend of the Headless Woman. According to folklore, a pirate had come to claim his bride when he found her in a wedding dress with another man. He cut off her head and threw it into the island. On full moon nights, the headless bride can be seen walking around the island looking for her head. Many times guests would be taken to the island to wait for the bride. Sometimes, Earl Shipley or Roger Pryor would pull a sheet over their head and walk the beach to prank viewers.

Hutchinson wrote that the famous flyer Charles Lindbergh once spent the night at the hotel after an oil leak forced his plane down during a training flight from the Navy Yard in Pensacola.


By 1946, the local area was nearly unrecognizable. Okaloosa County was established in 1915. Fort Walton Beach was incorporated in 1941.

Mary Esther residents decided to incorporate in 1946. The motivation was to build a sewer system.

“The citizens decided that if we didn’t incorporate, we were going to be overwhelmed by our neighbors,” Roger Pryor told the Okaloosa County Shopper in 1988.

According to a Daily News story from 1991, Roger Pryor noted residents organized to get funds for the facilities. The town had no credit, he said, but after the city was incorporated it was able to get a loan from the federal government for the sewer system.

Roger Pryor served as the town’s first mayor from 1946-47 and was re-elected in 1952.

In 1974, the city’s library was established. Mayor Tom Pryor and the town council were some of the first to donate books. An updated library was built in 1992.

The city continued to grow. A big boom for the economy was the Santa Rosa Mall, which opened in 1976.

Today, Mary Esther still holds that small-town charm as it keeps up with modern times.

“When I came back here to retire, I noticed it hadn’t changed much at all,” said Mayor Chris Stein, who was born in Mary Esther in 1958.  “The same names I grew up with are still here. I’m glad it didn’t grow up, I think it will stay like this for a long time.”