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Dale Herring transforms Bowlegs Town into literary adventure

H. Dale Herring (courtesy photo)

Real estate developer and businessman H. Dale Herring had no idea his new home was Bowlegs Town, a Seminole site packed with history.

When he found the property — located next to the Suwanee River — about 18 years ago, Herring originally intended to develop the land. After spending time in the area, however, he claims it became the ideal spot to live and care for his cattle. The story of Bowlegs Town “fell into his lap” when in 2015, Herring and archaeologist John Edwards stumbled upon artifacts tracing back to the Seminole Wars. The artifacts they found are evenly split between originating from the U.S. military and Seminoles.

“We started digging and 3,400 artifacts later, we found Bowlegs Town,” Herring said. “When you start doing the research and really digging into it, you find out how significant this site really was and is.”

Inspired by the discovery, Herring spent the past three years writing a book about Bowlegs Town. The book, “Bowlegs Town,” revolves around the adventures of two young boys, Billy Bowlegs and Tink, who grew up together as pledged blood brothers until the time came for them to part ways. In this piece of historical fiction, Billy became the chief of the Seminole Tribe and Tink went on to escape slavery.

The premise for the book is based on the Seminole Wars, which started in the early 1800s when Secretary of War John C. Calhoun ordered Gen. Andrew Jackson to invade Florida and attack the Seminoles. After the U.S. military killed Seminole Chief Cowkeeper, King Payne — the real Bolek “Billy” Bowlegs’ older brother — led the Tribe against the military and established numerous towns. When Payne was killed in 1812 after Col. Daniel Newman led a surprise attack, only a small group of Seminoles remained. Bowlegs assumed the leadership position and took the group to present-day Bowlegs Town, where he remained a prominent leader during the Second and Third Seminole Wars.

“This historical site is in my backyard. It’s such a significant site that’s always been overlooked,” Herring explained. “For years, the history books said the Seminole Wars took place along the Suwanee River, but they didn’t say where.”

The cover of Bowlegs Town (courtesy photo)

Other historical components of the book incorporate the Seminole Wars, the Suwanee River, Manatee Springs, Seminole culture and even the trial of Scottish trader Alexander George Arbuthnot and former Royal Marine Robert Ambrister, who were captured and executed by Jackson. Herring acquired the transcript of this trial and other historical events during his research. At 11 chapters and about 160 pages, the book serves as a small insight into a large piece of Seminole history.

“It was a project I really enjoyed. And now I want to do as much as I can as far as telling about the site and preserving it,” Herring said. “I created the stories in my mind. I took the historical facts and the research I did during the years and the artifacts we found and put them all together.”

Although he enjoyed the entire process of the making the book and is fascinated by all aspects of Seminole history, Herring said his favorite part of “Bowlegs Town” is Chapter 10: The Tall Stranger. The chapter focuses on a person who is seen as a mystical shadow figure riding his horse on the edge of town. While the figure refuses to speak to anyone else in the town, he regularly meets with Billy Bowlegs and counsels him about leadership. In some ways, Herring said he feels as if he is this character and ended up in Bowlegs Town to look after the history of the Seminoles.
“I’ve met some of the greatest people I’ve ever met through this process. I want to establish a stronger friendship with the Seminoles,” he said. “I feel them here; I feel them on my land. … Now that Bowlegs Town has been revealed, I feel a connection with the Seminoles.”

Though the self-proclaimed entrepreneur-at-heart typically invests his time into pursuing business ventures, he never thought of Bowlegs Town as a way to make money. To him, the most important part of this venture was to share the story of the unconquered Seminoles.

The book will be released on Oct. 1. Herring will host a book signing on Oct. 7 from noon to 3 p.m. at the Putnam Lodge in Cross City, Florida and on Nov. 4 at the Ah-Tah-Thi-Ki Museum’s American Indian Arts Celebration in Big Cypress.

Li Cohen
When she isn't drinking a [probably excessive] cup of coffee, Li is reading and writing about local, national and international news. She can also be seen running around NYC in preparation of marathon season and travelling to new lands. Make sure to check out her work at, send her an email at and follow her journeys on Twitter (@WritingLiYakira) and Instagram (@LiYakira).

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