Live Local: May Events
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St. Augustine Food + Wine Festival
May 3 through 7, 2023
Various Locations
St. Johns County, FL
On May 3rd through 7th, the St. Augustine Food + Wine Festival hosts a celebration of culinary excellence, showcasing local and celebrity chefs, premium beverages, live music and more at various locations across St. Johns County.
First Friday Artwalk
May 5, 2023 at 5 to 9 p.m.
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.
Be sure to stop by and visit STA Marketplace favorites including High Tide Gallery Art and Gifts as well as W.B. Tatter Studio Gallery. Reminder that you can take Old Town Trolley from the Governor’s House (corner of King and Cordova Streets) from downtown to participating galleries on Anastasia Island.
Unidos en la Musica
May 6, 2023 at 10 a.m. to 10 p.m.
Francis Field
29 West Castillo Drive, St. Augustine, FL, 32084
Unidos en la Musica returns to Francis Field on May 6, 2023
The festival is kid-friendly so bring the whole family to experience a day filled with Latin Music, Dance, Workshops, Art, Games, Food & Adult Beverages! Visit their Facebook page for performance times, activity details, workshops, and schedules.
St. Augustine Craft Brewers’ Fest
May 6, 2023 at 1 p.m. to 6 p.m.
Fountain of Youth Archaeological Park
11 Magnolia Avenue, St. Augustine, FL, 32084
Enjoy your Saturday 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 10 through May 13, 2023
Various Historic Locations
St. Augustine, Florida
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 2023 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!
Tour 20+ historic properties in St. Augustine, Florida from May 10-13, 2023 — many of which will showcase special events.
Tomato Festival
May 13 and 14, 2023
Wesley Wells Farms
2680 Ada Arnold Road, St. Augustine, FL, 32092
Wesley Wells Farms is excited to host their very first 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!
The event features include a Kids’ Zone, Salsa Tasting Contest, U-Pick Flowers and Veggies, Live Entertainment, Handmade Market and Best Homegrown Contest.
As If! The 90s Fest
May 20, 2023 at 1 p.m. to 9:30 p.m.
Francis Field
25 West Castillo Drive, St. Augustine, FL, 32084
As If! 90s Fest is back, ALRIGHT!! and they are going HUGE in 2023.
Join them for the 3rd year of this massively loved fest on May 20, 2023 from 1 to 9:30 p.m. on Francis Field in St. Augustine for the raddest summer kickoff event in Florida.
This year’s event’ features double headliners Vanilla Ice and Spin Doctors, a full line-up of regional musicians, an artisan market, massive kids’ zone, extensive VIP perks, $5 beers and everything you love about about the 90s.
Get your tickets on Eventbrite now!
Vilano Beach Artisan Market
May 20, 2023 at 4 to 8 p.m.
Vilano Beach Main Street
190 Vilano Road, St. Augustine, FL, 32084
The third Saturday of every month, head to the Vilano Beach Artisan Market. 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.
Lighthouse Plaza Art Show
May 21, 2023 at 10 a.m. to 4 p.m.
High Tide Gallery
850 Anastasia Blvd. St. Augustine, FL 32080
On May 21st head to High Tide Gallery for the Lighthouse Plaza Art Show.
Explore the works of and mingle with your favorite local artists as you take a Sunday stroll through the outdoor plaza on Anastasia Boulevard. Then, pop inside the gallery to discover the pieces of another 50 artists.
Visitors will love this free event with free parking featuring hundreds of locally made masterpieces.
Palatka Blue Crab Festival
May 26 through May 28, 2023
Riverfront Park and St. Johns Avenue
100 Memorial Parkway, 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 26, 27 and 28, this beloved event features national headliners including Molly Hatchet, Ying Yang Twins and Sugar Hill Gang plus full-day concert line-ups of regional musicians, the Blue Crab pageant, waterski show, firework show, dozens of vendors and food trucks, community events, activities, entertainment for all ages and a massive kids’ zone.
This family-friendly festival (which has been around for nearly 30 years!) takes place the Friday, Saturday and Sunday before Memorial Day in downtown Palatka and along the scenic waterfront.