Florida Historical Festivals & Events

May 24 - 26, 2019

Location: Stephen Foster Folk Culture Center State Park, White Springs, Florida

Learn about old Florida and the folk traditions of this great state at this festival. Jam sessions, demonstrations, and workshops are held throughout the weekend to teach you the ways of our ancestors.

May 29 - June 7, 2019

Location: Pensacola, Florida

This is a celebration of the founding of Pensacola by Spanish Conquistador, Don Tristan de Luna in 1559. Since then, the flags of five different countries have flown over the city: Spanish, French, British, Confederate, and American. The fiesta celebrates the multi-cultural heritage of Pensacola and its long history.

May 31 - June 1, 2019

Location: The Fort Walton Beach Landing, Fort Walton Beach, Florida

Head to the panhandle for one of the longest-running and most popular pirate festivals in the country! Check it out for a fun-filled weekend that ends in an unforgettable parade.

June 1, 2019

Location: Fountain of Youth, St. Augustine, Florida

On June 6, 1586 23 ships full of Englishmen under the command of Sir Francis Drake attacked the Spanish settlement of San Agustín. The town burned, but the Spanish returned to rebuild it and make it into the city it is today. This event is a reenactment of that day in the historical center of the city!

June 15, 2019

Location: Fort Mose, St. Augustine, Florida

Every year The 1740 Spanish victory at the Battle of Bloody Mose is reenacted in the place where it originally took place. This was the battle that forced the British to retreat from Spanish Florida keeping St. Augustine a Spanish territory. There is no better place to experience history first hand than here in Florida's oldest city!

July 11 - 13, 2019

Location: Key West, Florida

This event celebrates the famous $450 million dollar treasure discovery in the water's of Key West by Mel Fisher. It includes VIP tours of the Fisher Family’s Private Conservation Laboratory, a Schooner Wharf Bar Dock Party, and Treasure Hunting Boat Tours. 100% of all net proceeds from these events will benefit Wesley House Family Services, Inc.

July 16 - 21, 2019

Location: Key West, Florida

Famed author, Ernest Hemingway called Key West home for many years. The island celebrates his legacy each year on his birthday with look alike contests, prose and poetry readings, the “Running of the Bulls”, symposium presentations, a museum exhibit, and a three-day marlin tournament!

November 2 - 3, 9 - 10, & 16 - 17, 2019

Location: T.Y. Park, Hollywood, Florida

Explore our kingdom full of musicians, artisans, eateries, knights and jesters. Cheer for your favorite side at the living chess game and joust! Feast like a King on hearty food and drink. Shop for fine handcrafted treasures in the Artists’ Market. Enjoy challenging games and entertaining shows for all ages.

February 22 - 23, 2020

Location: Cypress Grove Park, Orlando, Florida

This is a festival to celebrate the rich culture and history of the Pine Castle area. Here you can vanish into the past with demonstrations, wild west shootouts, and carriage rides, plus tons of other activities for the whole family. In addition, delicious food and fun musical entertainment can also be found throughout the festival.