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.

Sponsored Partners

Lightner Museum of St. Augustine
Whiskey, Wine, and Wildlife
La Fiesta - Ocean Inn & Suites
La Fiesta - Ocean Inn & Suites
Beacher's Lodge - Oceanfront Suites
Beacher's Lodge - Oceanfront Suites
Women joining together to support breast cancer awareness
Saturday
Oct 11

Hastings Pink Walk

Saturday, Oct. 11, 2025 | 8:00 a.m. — 10:00 a.m.

Help raise awareness for breast cancer at this community fundraiser.

A woman riding a horse at the Cracker Day Celebration at Elton, FL
Saturday
Oct 11

Annual Cracker Day Festival

Saturday, Oct. 11, 2025 | 9:00 a.m. - 6:00 p.m.

Celebrate Florida cowboy heritage with games, food, and crafts.

A group of Greek-Americans dressed in their traditional clothing for the Greek Festival
Saturday
Oct 11

Greek Festival 2025

Saturday and Sunday, Oct. 11 and 12, 2025 | Times Vary

Enjoy Greek music, dancing; shop for Greek items, and take home Greek food.

The singing group Voctave, dressed for a performance
Saturday
Oct 11

EMMA Concerts: Voctave

Saturday, Oct. 11, 2025 | 7:30 p.m. to 9:30 p.m.

This 11-person group of vocalists perform songs from their newest album.

The Gamble Rogers concert stage at the Waterworks
Saturday
Oct 18

A Gamble Rogers Concert Series

Select Saturdays Oct. 18, 2025 - Jun. 20, 2026 | 7:00 p.m. - 10:00 p.m.

St. Johns County Cultural Council presents this concert series.

Tinsley Ellis plays his guitar against a backdrop featuring a world map.
Saturday
Oct 18

Tinsley Ellis at Cafe Eleven

Saturday, Oct. 18, 2025 | 8:00 p.m. - 10:00 p.m.

A blues bombshell known for the smash hit "Kiss of Death."

Cellist Ben Solee sitting in a wooded area with his cello
Tuesday
Oct 21

Black Box Session with Ben Sollee

Tuesday, Oct. 21, 2025 | Two Shows: 6:30 p.m. and 9:00 p.m.

Enjoy an intimate concert by cellist, singer, and songwriter Ben Sollee.

Two dogs and a cat depicted in Gilded Age finery
Thursday
Oct 23

Pin Up Paws: Gilded Paw Gala

Thursday, Oct. 23, 2025 | 6:00 p.m. - 9:00 p.m.

The 2026 calendar is revealed at this St. Augustine Humane Society fundraiser.

The audience at an outdoor blues and southern food fest sit at tables and in rows
Friday
Oct 24

St. Benedict Blues Festival 2025

Friday-Sunday, Oct. 24 - 26, 2025 | See Times Below

Enjoy gumbo, barbeque, and great blues performances at this annual festival.

EstuScary Haunted Trail flyer featuring a zombie on a trail surrounded by pumpkins and bats
Friday
Oct 24

EstuScary Haunted Trail

Fri.-Sun., Oct. 24-26, 2025 | Times Vary

A scary nighttime haunted trail walk, and trunk-or-treat fun for kids in the daylight.

Saturday
Oct 25

Jail Break 5K

Saturday, Oct. 25, 2025 | 8:00 a.m. - 10:30 a.m.

Lace up and make your escape.

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