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 festivity, or an authentic reenactment, there's always something BIG happening in this tiny town. From art exhibits and live theater to historical events and culinary creations, our can't-miss events feature the best of the nation’s oldest city.

A painter capturing the iconic architecture of St. Augustine during a Plain-Air Paint Out art event
Today
Apr 24

Plein Air Paint Out

Wednesday, Apr. 23 - Sunday, Apr. 27, 2025 | Times and Locations Vary

Watch — or participate in — the artistic magic of the "plein air" painting event.

Sponsored Partners

Lightner Museum of St. Augustine
2025 Food and Wine festival display
Ocean Sands Beach Boutique Inn
La Fiesta - Ocean Inn & Suites
La Fiesta - Ocean Inn & Suites
The Radzinski Garden at the Lightner Museum
Tomorrow
Apr 25

Paint & Picnic

Friday, Apr. 25, 2025 | 12:30 p.m.

Watch plein air artists paint as you picnic in the Radzinski Family Garden.

A stage, lit with blue light, with a full audience awaiting the performance
Tomorrow
Apr 25

Jazz Poetry Cafe

Fourth Fridays, Mar. 28 - Aug. 22, 2025 | 7:00 p.m. - 11:00 p.m.

This cabaret-style event features musical performances and the spoken word.

Saturday
Apr 26

K9s United 9K, 5K, & 1-Mile Run

Saturday, Apr. 26, 2025 | 8:00 a.m. and 9:00 a.m.

Honor K9 law enforcement at this World Golf Village running event.

The prize table full of baskets and an assortment of knick-knacks
Saturday
Apr 26

Cabbage, Potato, & Bacon Festival

Saturday - Sunday, Apr. 26 - 27, 2025 | Times Vary

Celebrate historic Hastings and its agriculture during this two-day event.

The Adventures in Plein Air exhibit will showcase work from the St. Augustine Art Association's 6th Annual Plein Air Paint Out.
Saturday
Apr 26

Live Plein Air Painting Demo

Saturday, Apr. 26, 2025 | 11:00 a.m. - 1:00 p.m.

Join Plein Air judge, Steven Walker, for a live painting demonstration.

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.

Art lovers browse the galleries on Aviles Street at the Friday Night Art Walk in St. Augustine, FL
Friday
May 2

First Friday Art Walk

First Friday of each month | 5:00 p.m. - 9:00 p.m.

A monthly celebration of art throughout St. Augustine's galleries.

Three rows of the Key of Seas student choir at Flagler College
Friday
May 2

Romanza: Key of Seas

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

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

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.”

Four members of a woodwind quartet, wearing black and holding their instruments are arrayed before a grand piano,
Monday
May 5

Romanza: 9B Woodwind Quartet

Monday, May 5, 2024 | 12:00 p.m. - 1:00 p.m.

Four woodwind musicians perform for Romanza's Chamber Music Series.

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

Great food, wine, and more at three locations over five days.

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