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How Indie Flea became a St. Petersburg staple

As the monthly market celebrates its 10th year, founder Rosey Williams looks back.
Rosey Williams, the founder of Indie Flea poses for a portrait at the Indie Flea Market on Saturday, Oct. 5, 2019 in St. Petersburg. The market is returning — and celebrating a decade in St. Petersburg — on Oct. 9.
Rosey Williams, the founder of Indie Flea poses for a portrait at the Indie Flea Market on Saturday, Oct. 5, 2019 in St. Petersburg. The market is returning — and celebrating a decade in St. Petersburg — on Oct. 9. [ LUIS SANTANA | TIMES | Tampa Bay Times ]
Published Oct. 5|Updated Oct. 5

Before Rosey Williams created Indie Flea, Tampa Bay’s wildly popular monthly street market, there was Dog Street.

Back in the 1980s and ‘90s, the vintage store run by Williams’ parents was a staple of the 600 block of St. Petersburg’s Central Avenue. The Sunshine City was still sleepy back then, but there was a deep sense of community. And, along that strip of Central, lots of great vintage stores.

Because Williams grew up in this old-school art community, it makes sense that she would start her own vintage shop, Ramblin’ Rose, on the same street. Ten years ago, the secondhand wonders and artist-made goods spilled out onto the streets when Williams hosted the first Indie Flea market.

Her monthly market is still going strong, though it has morphed and grown along with the city.

The first Indie Flea of the season, rescheduled after Hurricane Ian, kicks off from noon to 4 p.m. Sunday at 14 18th St S. in St. Petersburg’s Grand Central District. There will be a market on the first Sunday of the month through April. (January’s market date falls on the 8th, due to New Year’s Eve.)

“I want to keep this going for the family,” Williams said. “I want you to come and get a piece of the old St. Pete.”

Rosey Williams is pictured as a baby alongside her parents, Jeff and Mary Lynn Williams, at the family’s second-hand shop, Dog Street, in this St. Petersburg Times clip from 1989.
Rosey Williams is pictured as a baby alongside her parents, Jeff and Mary Lynn Williams, at the family’s second-hand shop, Dog Street, in this St. Petersburg Times clip from 1989. [ Newspapers.com ]

Williams, 33, was born and raised in St. Petersburg, where she often hung out downtown. After she graduated from high school, she spent time traveling the country before coming back to her hometown to open Ramblin’ Rose. Her trips to the West Coast, Colorado and other progressive areas inspired her to start throwing community-conscious events involving local artists and musicians.

The Indie Flea was one of these. In the early days, bands played avant-garde synthesizer music on the sidewalk — without permits. Williams invited unhoused people in the neighborhood to set up random objects. It was less curated than it is today, but it was a blast.

“All the fancy neighbors didn’t like it,” Williams said. “It was a truly wide range of experimental hustlers trying to make money.”

Hundreds of people attend the Indie Flea Market on Saturday, Oct. 5, 2019, in St. Petersburg. The market is returning — and celebrating a decade in St. Petersburg — on Oct. 9.
Hundreds of people attend the Indie Flea Market on Saturday, Oct. 5, 2019, in St. Petersburg. The market is returning — and celebrating a decade in St. Petersburg — on Oct. 9. [ LUIS SANTANA | TIMES | Tampa Bay Times ]

Manny Kool, who runs Daddy Kool Records, remembers those early market days. Back then, his shop was on the same block as Ramblin’ Rose. He helped whenever he could, from sponsoring events to printing flyers.

“Everybody felt invigorated and like we were onto something new and exciting,” he said. “Every Saturday the Indie Flea was there was the best Saturday the store had for the month.”

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Indie Flea is celebrating a decade of business in St. Petersburg.
Indie Flea is celebrating a decade of business in St. Petersburg. [ © BECKY RUDOLF 2021 | Courtesy of Indie Flea ]

Over the years, Williams has tried a lot of different things. For one, she closed the brick-and-mortar location of Ramblin’ Rose to focus on the market. (Williams still does wardrobe styling for artists under the business name.) She’s expanded to other cities, hosting events in Miami and Gainesville. She’s even done popups in other states.

“We don’t have a storefront. We just sort of adapt in the streets, in parking lots and alleys,” she said. “We just try to maintain the fabric and the culture of St. Pete and the old-school roots of the cool artists and the progressive concepts.”

Shoppers browse through racks of vintage clothing at a 2021 Indie Flea event in St. Petersburg.
Shoppers browse through racks of vintage clothing at a 2021 Indie Flea event in St. Petersburg. [ © BECKY RUDOLF 2021 | Courtesy of Indie Flea ]

While years past have included lucrative Tampa fleas in venues like Armature Works and Hotel Haya, lately Williams has struggled to find a venue to host events on that side of the bay. She is looking for Tampa venues for future markets, as well as sponsors.

“We’re stable and we’re confident but we are looking for sponsors and we have bigger plans,” said Williams. “We’re a small female-owned company. We don’t want to jack up the prices, but we’re affected too.”

Finding a consistent location in St. Pete has also been tricky, as gentrification has changed the landscape of the area.

“We’ve been kicked out of almost every neighborhood because of the developers and it getting too expensive,” she said. “We’re still feeling really resilient.”

A booth for Rad Harbor Vintage during a holiday-themed Indie Flea event in December 2021. For the 2022 market season, Indie Flea is returning to this location at 1418th St. S in St. Petersburg.
A booth for Rad Harbor Vintage during a holiday-themed Indie Flea event in December 2021. For the 2022 market season, Indie Flea is returning to this location at 1418th St. S in St. Petersburg. [ © BECKY RUDOLF 2021 | Courtesy of Indie Flea ]

As the tradition enters a new decade, there are some updates Williams is excited to share. The season will be longer than usual, to take advantage of the pleasant weather and increase in tourism. There will be more food and beverage options, plus a custom-built skate ramp. The markets will now take place on Sundays instead of Saturdays.

The coming events will feature close to 150 vendors, who will rotate each month. Williams, who splits her time between Nashville and St. Petersburg, is inviting traveling makers from Tennessee to peddle their creations. It all builds on a core principle of the event: giving artists a platform to support their business.

“It’s been cool to see the outreach and the different vendors grow,” Kool said. “How many people who have a brick and mortar started at Indie Flea? That is a real impact.”

Magazines for sale at Indie Flea during the 2021 season. The market returns for its 2022 season on Oct. 9.
Magazines for sale at Indie Flea during the 2021 season. The market returns for its 2022 season on Oct. 9. [ © BECKY RUDOLF 2021 | Courtesy of Indie Flea ]

If you go

The St Pete Indie Downtown Flea takes place Sunday. This season, the market returns on the first Sunday of each month through April (except on Jan. 8). Each event occurs from noon to 4 p.m. under a shaded overpass at 14 18th St. S in St. Petersburg’s Grand Central District. Events are free to attend and face coverings are encouraged. Visit theindieflea.com, facebook.com/theindieflea and instagram.com/indieflea.

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