It’s hard to imagine, among the pristine lawns and wandering museumgoers at The John and Mable Ringling Museum of Art today, that armored jousters on brawny horses once lowered their lances not far from the statue of David. Children clung to one another atop baby elephants draped in ornamental cloths, and a princess in a bedazzled hennin—a cone-shaped headdress—glided alongside bellydancers, mimes, sitar players and artisans. 

It was the late 1970s, and the Renaissance fair began as a vision of New College of Florida European history professor Lee Snyder: a campus conference of scholarly presentations, historical enactments, music and merriment. Led by the students, the conference became wildly popular, so much so that it was moved next door to The Ringling Museum and renamed the Sarasota Medieval Fair. Eventually, outside management ran the event before it dissolved in 2001. Horses pounding across the Ringling lawn, throwing up chunks of sod, wasn’t exactly compatible with preserving the museum’s stately historical setting.

Three years later, in 2004, Jeremy Croteau, a 17-year-old who grew up attending the fair, decided Sarasota deserved to have it back. With the support of his parents and a handful of enthusiastic volunteers, the fair was reborn. Twenty-one years later, Croteau remains at the helm, and the free-spirited, community-minded ethos that first took root beneath the banyans at The Ringling has found a permanent home at Mallaranny Farms in Myakka City—the only fair of its kind in Florida to own and operate a permanent location.

Like the medieval festivals that inspired it, the fair attracts traveling entertainers from across the country, artisans peddling handcrafted wares and local performers bringing their immersive acts, bawdy humor and centuries-old traditions to the woody village. “Around our third year, momentum had really built up,” says Shannon Bowden, the festival’s spokeswoman, who worked alongside Croteau to revive the fair all those years ago.

Soon, they were able to hire full-time traveling actors, “like hippies,” she says with a laugh. “Road rennies,” as they’re sometimes called, travel year-round from festival to festival, chasing warm weather. “When people say the circus is in town, that’s exactly how it is with [the festival crowd],” she says.

They swallow swords, befriend birds of prey, hula hoop with barbed wire and spend much of the year playing the bagpipes in a Celtic comedy band. It’s unconventional, but the discipline it takes turns passions into professions. Some of the iconic acts, like the Washing Well Wenches, which return every year, are franchised. Members of the all-female troupe—which notoriously provide “good clean fun” from “wet dirty women”—have been featured on well-known TV shows, performed on major studio albums and even written children’s books.

Locals get into the act, as well, and receive the equivalent of intensive acting instruction, everything from historically accurate dialect coaching to stage combat and stunt training. Then, in a move that would shock many of us who can barely commit to what we’re doing this upcoming Saturday, they spend every weekend rehearsing for more than three months leading up to the festival.

And for a surprising many, that family extends beyond the grounds—a truth Bowden knows well. She started in the fair in the late 1990s, when she met Dean, a career jouster, during auditions. “He had no idea I thought he was cute,” she says. They were cast as husband and wife, and soon, they weren’t acting. The two began dating before the festival started, and he proposed (in costume, of course) in 2007, at the wrap-up meeting at the end of the year’s run. Their three children all carry Arthurian-inspired names, and the proverbial apples have not fallen far from the tree—all of them are actors, and two perform in other Renaissance fairs.

While the fair’s pubs are lively and some performances can be raunchy, Bowden says what sets the Sarasota Medieval Fair apart is the effort to make it a place where families feel welcome. There are dozens of family-friendly acts, and the Children’s Realm offers crafts, dress-up, storytime, and even a medieval manners class. Kids can partake in a Knighting Ceremony each day and visit Father Christmas on the final weekend of the run in December. “It’s put on by families, for families,” Bowden says.

That doesn’t stop some guests from testing the limits, though. Over the years, attendees have arrived in everything from revealing fantasy costumes to little more than body paint. “If you can’t wear it to Disney, you can’t wear it here,” Bowden says.

Today, the fair has grown from a few thousand visitors on borrowed land to one of the region’s most beloved traditions, drawing tens of thousands of guests each season. The fair’s organizers are expanding their lineup next year with the launch of a new, standalone fantasy festival: The Great Imaginarium, featuring everything from a Lord of the Rings-inspired “shire” realm to an immersive storybook realm featuring the tales of Alice in Wonderland, Peter Pan and more.

For a few weekends each fall, the Woods of Mallaranny offer respite from the slog of emails and invisible social rules that structure everyday life. Some come to lose themselves in another century, others to indulge an obscure fascination or finally wear the costume that’s been hanging in their closet for years. Still others simply want a weekend where their family can trade screens for sword fights and make-believe. Whatever draws them in, everyone seems to find their place—whether they’re carrying a longbow, a turkey leg or merely the willingness to let loose and see what curiosities the day has in store.