May 2026 Events
First Friday Artwalk
May 1, 2026
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.
Fit Street Market
May 2, 2026
Francis Field
25 West Castillo Drive, St. Augustine, 32084
Head to Francis Field on May 2nd for a morning of fitness, wellness, and community. Participate in the community 5K run, free fitness classes including yoga, pilates, and more. Plus, shop the wellness vendor market featuring local health and fitness brands.
STA Craft Brewers’ Fest
May 2, 2026
Fountain of Youth Archaeological Park
11 Magnolia Avenue, St. Augustine, FL, 32084
Hopefully you were lucky enough to snag tickets for the STA Brewers’ Fest before they sold out! This one-of-a-kind festival is held annually at the beautiful Fountain of Youth Archaeological Park.
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 6 through 10, 2026
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 2026 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 6th through May 10th, 2026
Multiple Venues
Hyatt Place St. Augustine/Vilano Beach & Ancient City Farmstead
On May 6th through 10th, 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. Experience individual events or get the full package to attend all four days:
May 6th: The Saltworks Supper
May 7th: Harvest Awards & Tastings
May 8th: ST. A Soirée
May 9th: Grand Tasting
Unlimited culinary and beverage tastings included with all tickets!
Sunflower and Tomato Festival
May 9, 2026
Wesley Wells Farms
2680 Ada Arnold Road, St. Augustine, FL, 32092
The 4th Annual Sunflower & Tomato Soirée is happening at at Wesley Wells Farm on May 9th!
Golden fields. Heirloom flavor. Slow spring moments. This event is a one-day celebration held during peak sunflower bloom and tomato season.
Wander through acres of sunflowers in full glory, sip fresh lemonade in the brand-new Sunflower Lounge, and experience the farm in its most vibrant season.
Lullaby of the Rivers Festival
May 31, 2026
Limelight Theatre
11 Old Mission Avenue St. Augustine, FL 32084
The Lullaby of the Rivers Festival features outstanding live music on the Main Stage throughout the weekend. A second stage in the Community Center offers entertainment by Storytellers and an Open Mic, with tables where people can eat while enjoying performances. Food trucks and vendors are located nearby.