May 2025 Events
First Friday Artwalk
May 2, 2025
Historic Downtown and Anastasia Island
St. Augustine, FL
The Art Galleries of Saint Augustine founded and sponsors the award-winning First Friday Art Walk event on the first Friday of every month. Galleries open their doors from 5 to 9 p.m., offering new art exhibits and lively receptions to the public.
Romanza Festival
May 2 through 18, 2025
Multiple Venues
St. Augustine
St. Augustine’s Romanza Festivale of MUSIC and The Arts returns in 2025 with two weeks of daily events beginning May 2nd through May 18th.
The annual event features dozens of concerts, shows, exhibits and much more at locations throughout the city, showcasing productions by dozens of St. Augustine’s talented Arts and Cultural nonprofit organizations.
Most events are FREE!
STA Craft Brewers’ Fest
May 3, 2025
Fountain of Youth Archaeological Park
11 Magnolia Avenue, St. Augustine, FL, 32084
Enjoy your Saturday from noon to 5 p.m. at this one-of-a-kind festival held at the beautiful Fountain of Youth Archaeological Park.
The STA Brewers’ Fest features local breweries including Old Coast Ales, Ancient City Brewing, Bog Brewing and Dog Rose Brewing as well as regional Florida breweries, food trucks, live music and more!
St. Augustine History Festival
May 7 through 11, 2025
Multiple Venues
St. Augustine, FL
The St. Augustine History Festival was created and conceived by UFHSA (University of Florida Historic St. Augustine, Inc.) and the Lastinger Family Foundation for the purpose of generating excitement about the history of America’s oldest city.
The goal is to showcase every era of St. Augustine’s long and storied past, from the founding in 1565 to the most advanced technology available in 2025 to research and study every year in-between. American history began here, and no one tells the story better than they do – come out and enjoy the city!
St. Augustine Food + Wine Festival
May 7th through May 11th, 2025
Multiple Venues
La Cocina at the Cellar Upstairs, Hyatt Place St. Augustine/Vilano Beach, Ancient City Farmstead
On May 7th through 11th, enjoy a celebration of culinary excellence that showcases local and celebrity chefs, restaurants and their unique dishes as well as hundreds of varieties of wines, beers, and spirits. Participate in individual events or get the full package to attend all five days:
May 7th: River Walk Tastings
May 8th: Harvest Awards & Tastings
May 9th: Smoke on the Walk
May 10th: Grand Tasting
May 11th: Mother’s Day Jazz Brunch
Culinary & beverage tastings included with all tickets!
Evening at the Estuary
May 8, 2025 at 6 p.m.
Pesca’s by Michael’s at Hyatt Place
117 Vilano Road, St. Augustine, FL, 32084
Celebrate 25 incredible years of the GTM Research Reserve and Friends of GTM on May 8th at 6 p.m. This special silver-studded celebration will take place at the Hyatt Place in Vilano Beach/St. Augustine, where we’ll enjoy family-style dining from Pesca by Michael's with breathtaking views. Music and Dancing by Sidewalk 65!
Sunflower and Tomato Festival
May 10, 2025
Wesley Wells Farms
2680 Ada Arnold Road, St. Augustine, FL, 32092
Wesley Wells Farms, the largest you-pick farm in St. Johns County, is excited to host the second annual Tomato Festival.
They are packing in the fun for this fun, spring festival on the farm and there is fun for visitors of all ages for this special one-day event!
Vilano Beach Artisan Market
May 17, 2025
Vilano Beach Main Street
190 Vilano Road, St. Augustine, FL, 32084
The third Saturday of every month, head to the Vilano Beach Artisan Market from 4 to 8 p.m. This cool market lines the beautiful sidewalks of Vilano Road and hosts dozens of vendors and artists.
A perfect evening is in store as you sip a glass of wine or a cold beer from the cash bar , shop locally made goods, sway to the music and stop in at Puccini’s to purchase a delicious hot slice of pizza.
Palatka Blue Crab Festival
May 23, 24 and 25, 2025
Downtown Palatka
Palatka, FL 32177
Get ready to throw your claws in the air on Memorial Day weekend during the annual Palatka Blue Crab Festival!
Happening May 23, 24 and 25, this beloved event features national headliners, full-day concert line-ups of regional musicians, hundreds of vendors and food trucks, community events, a midway, and a massive kids’ zone. Visit their website for details.