Cannon Firing at the Castillo de San Marcos

Can't-Miss Events

Find the latest and greatest events in the oldest city.

Throughout the year, St. Augustine hosts unforgettable festivals, live music, and cultural celebrations. Whether it’s a nationally recognized music festival, a holiday celebration, or an authentic reenactment, there's always something BIG happening in St. Augustine. From art exhibits and live theater to historical events and culinary celebrations, our can't-miss events feature the best of the nation’s oldest city.

The winner of the men's division for the 2021 Race to the Taste in St. Augustine.
Sunday
Apr 27

Race to the Taste 5K

Sunday, Apr. 27, 2025 | 10:30 a.m.

Lace up your sneakers and savor every moment of this annual culinary 5K.

Sunday
Apr 27

A Taste of St. Augustine 2025

Sunday, Apr. 27, 2025 | 11:00 a.m. - 4:00 p.m.

Sample a wide variety of St. Augustine cuisine at this popular annual food festival.

The 5th Annual St. Augustine Plein Air Paint Out will culminate in an art exhibit at the St. Augustine Art Association May 7, 2021.
Sunday
Apr 27

Plein Air Pop-up Exhibit

Sunday, Apr. 27, 2025 | Noon to 6:30 p.m.

Discover stunning works from the 2025 Plein Air Paint Out

Bandmates from Wilco lay on a gray floor and pose for fans.
Wednesday
Apr 30

Wilco at St. Augustine Amphitheatre

Wednesday, April 30, 2025 | 7:00 p.m. - 10:00 p.m.

A Grammy-winning band celebrated for their fusion of rock, folk, and experimental styles.

A Classic Theatre presents "The Immigrant" on two weekends in May 2022 at the St. Augustine Waterworks.
Friday
May 2

A Classic Theatre: The Foreigner

Fridays - Sundays, May 2 - 11, 2025 | Times Vary

This award-winning comedy is frequently produced by college and local theaters.

Audience under a shower of confetti at As If! The 90s Fest 2023
Saturday
May 3

As If! The '90s Fest

Saturday, May 3, 2025 | 2:00 p.m. - 9:00 p.m.

Slip your Game Boy in your Starter jacket and celebrate at the “As If! The ’90s Fest.”

Three rows of the Key of Seas student choir at Flagler College
Sunday
May 4

Romanza: Key of Seas

Saturday, May 2, 2025 | 7:30 p.m. - 9:00 p.m.

Romanza 2025 opens with Flagler College's Key of Seas vocal ensemble.

The Government House will be featured as part of the St. Augustine History Festival.
Wednesday
May 7

St. Augustine History Fest, 2025

Wednesday, May 7 - Sunday, May 11, 2025 | Times and Locations Vary

St. Augustine hosts the fourth annual history festival in May of 2025.

A glass of white wine and a plate of food sitting on a rustic table by the water
Wednesday
May 7

St. Augustine Food + Wine Festival

Wednesday, May 7 to Sunday, May 11, 2025 | Times and Locations Vary

Hosting five events featuring food and wine, held at four different locations.

Piles of tomatoes of various colors
Saturday
May 10

Sunflower and Tomato Festival 2025

Saturday, May 10, 2025 | 9:00 a.m. - 5:00 p.m.

Visit a thriving family farm, purchase produce, and take part in the festivities.

Reenactors participate in Drake's Raid on St. George Street in St. Augustine.
Saturday
May 10

Drake's Raid Reenactment

Saturday, May 10, 2025 | 7:00 p.m. - 9:00 p.m.

Members of Florida Historic Militia reenact Sir Francis Drake's siege of San Agustin in 1586.

A dancer in a ballet pose dressed as Rapunzel
Saturday
May 17

St. Augustine Ballet: "Rapunzel"

Saturday, May 17, 2025 | 1:30 p.m. & 7:00 p.m.

Experience the tale of a trapped girl in a tower awaiting freedom and love.

The composer and pianist Sergei Rachmaninoff seated at the piano
Sunday
May 18

Romanza Festivale: "Rach 2 by 6"

Sunday, May 18, 2025 | 5:00 p.m. - 6:30 p.m.

Six musicians perform Rachmaninoff's Piano Concerto No. 2 for Romanza's final event.

Friday
May 23

Blue Crab Festival 2025

Friday, May 23 - Sunday, May 25, 2025 | Times Vary

Eat delicious seafood with the company of live music and family activities.

Editor's Note: We encourage you to verify event times and details with the organizers, as they may change.