Violinst Luca Ciarla gesturing with his bow, on stage in front of a yellow background

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.

This charity 5K run/walk promotes breast cancer awareness and raises money for early detection services.
Saturday
Oct 4

Pink Up the Pace 2025

Saturday, Oct. 4, 2025 | 8:00 a.m. - 12:00 p.m.

Promoting breast cancer awareness and raising money for early detection.

A natural healing session taking place
Sunday
Oct 5

Florida Bohemian Festival

Sunday, Oct. 5, 2025 | Noon - 8:00 p.m.

Connect the mind, body, and spirit at this one-day event.

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.

Votave, an 11-member a capella group, wearing black, standing together against a white wall
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.

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.

Saturday
Oct 25

Jail Break 5K

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

Lace up and make your escape.

Historic re-enactors showcase the food that was grown and eaten at Fort Mose in the mid-1700s.
Saturday
Nov 1

Fort Mose First Harvest

Saturday, Nov. 1, 2025 | 9:30 a.m - 3:00 p.m.

This harvest celebration includes cooking demonstrations and a farm market.

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