Gulfport's November Calendar Has a Second Main Street, and It's 49th Street South

On Saturday, November 14, Gulfport has three events at once, in three parts of the city. At 8 a.m., Mayor Love checks walkers in at Pavilion #6 on Gulfport Beach for the Mayor's Community Walk on the Discover Gulfport Walking Trail. From dawn to dusk, the Permit Free City-Wide Yard Sale runs on driveways all over the city. At 10 a.m., the Blues, Art & Seafood Festival opens at Trolley Market Square, 4900 Tangerine Ave. S., and runs until 8 p.m.

The city's community news page lists all three. Only one is on the water. The others are inland, and a resident-led group from the 49th Street corridor is hosting the festival.

The Waterfront Lost a Venue and Renamed Two Events

For years, Gulfport's social calendar has centered on Beach Boulevard and Shore Boulevard. That's still where the Tuesday Fresh Market runs every week of the year, 9 a.m. to 2 p.m., and where the Witches Walk ends at the Shore Boulevard Block Party on Halloween night.

The waterfront calendar has changed in two ways. The city's Casino page still says the Historic Gulfport Casino is closed until further notice because of damage from Hurricanes Helene and Milton. Art Walk and IndieFaire no longer run under those names. They are now the Gulfport Night Market, held 5 to 9 p.m. on the first Friday and third Saturday of every month. The Gulfport Merchants Chamber presents it with Tampa Bay Markets, and the vendors sell art, jewelry, clothing, pet products and packaged artisan foods.

The storefronts are changing too. The Gabber's September business roundup reported that The Wine House at 2913 Beach Blvd. S. closed September 13. The same owners still run Gulfport Brewery Eatery at 3007 Beach Blvd. S., and several Wine House team members now work there. A few doors down, St. Pete Rising reports that Nanday Café is coming to 3107 Beach Boulevard South, the former GulfPerk Coffee Bar space, with plans for coffee, breakfast and lunch. No opening date or hours had been announced in that report.

The waterfront is still busy. But with the Casino closed, the calendar has been filling up elsewhere, and a lot of it is on the 49th Street side of town.

The People Who Organized 49th Street

The Blues, Art & Seafood Festival is presented by the Fusion 49th District together with the City of Gulfport. The city describes it as live blues, local art and vendors, seafood and other food, and community activities "along the 49th Street corridor."

Fusion 49th is not a city department. St. Pete Catalyst described it in March 2025 as a community-led 501(c)(3), a partnership between St. Petersburg and Gulfport covering 49th Street from 2nd Avenue N. to 24th Avenue S. The group first met in 2023. At the time of that report, it was working on tree coverage and sidewalk improvements and holding corridor cleanups, with public meetings on the first Monday of each month at the Gulfport Resource Center.

When the group turned two in June 2025, Bay News 9 reported that its members included business owners, residents and city leaders from both cities. Projects included a Sunday market, hurricane-readiness help, and new committees on the economy, community outreach and beautification. Co-founder Brother John Muhammad told the station that the goal is for people who live and work on the corridor to lead its projects themselves. Julio Pagan of Julio's Empanadas told Bay News 9 that Fusion's networking and referrals had helped his business and that foot traffic on the corridor was growing.

That's the background for November 14. The festival didn't come from a downtown merchants group. It came from a group organized around one commercial street that runs through two cities.

A Plaza the City Built for This Purpose

The city's page for Trolley Market Square puts it at Tangerine Avenue and 49th Street South. The plan was to call back the old trolley route with a replica trolley and connect businesses across the 49th Street redevelopment area.

Building it took real money. The city's 49th Street annual report for FY 2021/2022 says the construction bid was awarded on September 18, 2018, for $379,557.05. The report also describes $300,000 in Community Development Block Grant funding and about $150,000 spent removing contaminated fill from the site. The cleanup alone cost about 40 percent as much as the construction bid. A full day of blues and seafood on that site, put on by a resident-led district, is the kind of use the city's plan describes.

Red Feather's First Sundays

Two weeks earlier, the corridor has a smaller event that repeats every month. The 49th St. Makers & Growers Market runs 11 a.m. to 3 p.m. at Red Feather Studio, 1301 49th St. S., on the first Sunday of each month through May 2, 2027. It has local products, health and living goods, handmade items and live music outdoors. November 1 is this season's first date on the city calendar. The next first Sunday after that is December 6.

Red Feather Studios describes itself as a shared creative workplace on the commercial stretch of south 49th Street. It has studio space, an indoor classroom and event space, and a garden patio. It lists Eat Be Grow, Gulfport Food Forest, Artful Earthscapes and Overachieving Tea Company as associated businesses and organizations. The studio calls its market a "supportive incubator for first time marketeers."

Also on November 1, at 3 p.m., the New Horizons Concert and Jazz Bands of Gulfport play a free Music in the Park show at the Clymer Park Pavilion, 2215 Beach Blvd. S. Bring a chair. Donations help cover the bands' costs. You can go to the market at midday and the concert in the afternoon.

A Labyrinth Taking Shape on 28th Avenue

The third inland project isn't on 49th Street, but it follows the same pattern. Artists and volunteers are building something for the long term, away from the water. At the Gulfport History Museum, 5301 28th Ave. S., the TimeWeaving Community Labyrinth project has two free evenings in November.

• Friday, November 6, 5 to 8 p.m.: a labyrinth lit by luminaries, with a dance and drum performance by Hip Expression Dancers and Drummers. RSVP through the Gulfport Historical Society.
• Friday, November 20, 4 to 6 p.m.: a Land Blessing and Thanksgiving Address dedicating the future site of Gulfport's permanent labyrinth. Afterward, visitors make their own art objects, which become part of a shared labyrinth installation. RSVP here.

Creative Pinellas lists the November 20 program as the launch of the labyrinth's foundation ceremony and a collection of materials for a 2050 time capsule. Creative Pinellas names Ingrid Bredenberg as TimeWeaving's creator, social artist and project manager, with a background in labyrinth design and community engagement. The project is part of Creative Pinellas' Art Everywhere program. Creative Pinellas reported that the program split $350,000 among nearly 30 organizations and artists this fall.

November, by Date and Area

Front yards are part of the calendar too. On Saturday, November 7, from 10 a.m. to 4 p.m., local artists show and sell original work in their own yards for the city's Art in the Yard Community Art Sale. If it rains, the sale moves to Sunday, November 8. The city posts a Google map of participating artists.

Here is the rest of the month on the city's calendar, in date order, with the part of town for each event.

The Veterans Parade is open for registration until 3 p.m. on Monday, November 2, at the city's Heroes Weekend page. The tree giveaway and the Swap & Drop both require proof of Gulfport residency. Swap & Drop is run by the city, Gulfport Grassroots and Keep Pinellas Beautiful. It works as a drive-through, so keep your items easy to reach in the trunk, back seat, truck bed or trailer.

Where to Eat Between Stops on 49th

Between Red Feather and Trolley Market Square, the corridor has places to eat that have been around for years. At 1411 49th St. S., Island Flavors and Tings is a restaurant, grocery and catering business. Owner and chef Helena Josephs has run it since 2006. The Gabber's August roundup reported that she just launched Hot Tings, her first line of bottled hot sauces. The sauces are built on Scotch bonnet peppers and come in tamarind, mango pineapple, and aged rum varieties.

Farther south, Julio's Empanadas lists its address as 2201 49th Street South and advertises breakfast service. On its site, it's open until 8 p.m. on Fridays and Saturdays and from 11 a.m. to 5:30 p.m. on Sundays. It's worth checking the site before you go, since hours change.

Businesses on the corridor open and close too. The same Gabber roundup reported that Heavenly Eats & Sweets at 2025 49th St. S. closed August 16, about a year after it opened in July 2025. The owners said they are working toward reopening in Treasure Island or Madeira Beach.

Silver and Welch Collective keeps track of how Gulfport's streets and corridors are changing, from the Casino's reopening to new businesses along 49th Street. If you'd like to talk about what that change means for your own block, schedule a free consultation.