Cannon Firing at the Castillo de San Marcos

Can't-Miss Events

Find the Ancient City's latest and greatest events.

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.

The crowd of runners and walkers warming up for the Donna 5K at TPC
Saturday
Oct 10

Donna 5K at TPC Sawgrass

Saturday, Oct. 10, 2026 | 8:30 a.m. start

Support the fight against breast cancer at this 5K.

A montage of Greek foods and a child in Greek clothing
Saturday
Oct 10

Greek Festival 2026

Saturday and Sunday, Oct. 10 and 11, 2026 | Times Vary

Savor, sip, shop and enjoy Greek music and dancing, then take food home.

Comedian Danny Johnson, in a blue suit with blue glasses
Saturday
Oct 17

Danny Johnson, Stand Up Comedy

Saturday, Oct. 17, 2026 | 7:00 p.m. to 9:00 p.m.

Making people laugh with observational, clean humor about everyday life.

The audience at an outdoor blues and southern food fest sit at tables and in rows
Friday
Oct 23

St. Benedict Blues Festival 2026

Friday-Sunday, Oct. 23 - 25, 2026 | See Times Below

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

A group of costumed runners in prision black and white and one animal
Saturday
Oct 24

10th Annual Jail Break 5K

Saturday, Oct. 24, 2026 | 8:00 a.m. - 10:30 a.m.

Lace up and make your escape from the Old Jail.

EstuScary Haunted Trail flyer featuring a zombie on a trail surrounded by pumpkins and bats
Thursday
Oct 29

EstuScary Haunted Trail

Thursday through Saturday., Oct. 29-31, 2026 | Times Vary

A scary nighttime haunted trail walk for brave kids and adults.

A female chef with her dishes
Friday
Nov 6

Lincolnville Festival, 2026

Friday, Nov. 6 - Sunday, Nov. 8, 2026 | See Times Below

The annual festival offers three days of live music, dancing, and family activities.

Historic re-enactors showcase the food that was grown and eaten at Fort Mose in the mid-1700s.
Saturday
Nov 7

Fort Mose First Harvest

Saturday, Nov. 7, 2026 | 9:30 a.m - 3:00 p.m.

This harvest celebration includes cooking demonstrations and a farm market.

Live music being played under the gazebo
Saturday
Nov 21

Light-Up! Night

Saturday, Nov. 21, 2026 | 4:00 p.m. - 7:30 p.m.

Nights of Lights begins with music and the ceremonial flip of the switch.

The duo Mama's Broke depicted in front of a shiny curtain in a tintype style
Friday
Dec 4

Mama's Broke at the Waterworks

Friday, Dec. 4, 2026 | 7:30 p.m. - 9:30 p.m.

The Canadian duo both sing, write songs, and play multiple instruments.

Saturday
Dec 5

Christmas Parade 2026

Saturday, Dec. 5, 2026 | 9:00 a.m - 10:30 a.m.

Celebrate the holiday season at St. Augustine's annual parade featuring Santa.

Members of the garrision marching through the City Gate during Colonial Night Watch
Saturday
Dec 5

Colonial Night Watch

Saturday, Dec. 5, 2026 | 7:00 to 8:00 p.m.

Experience St. Augustine history and join a torch-lit parade.

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