Skip to main content

Colonial Oak Music Park concert

All St. Augustine Events

The Oldest City is known for its unique and plentiful events.

As the longest European-occupied settlement in the United States, St. Augustine is recognized as the nation’s oldest city and the host of many major events. St. Augustine's annual celebrations reflect this rich heritage and culture, where visitors and locals convene on historic downtown's brick streets. Our Calendar of Events lists all the gathering—big and small—whether they're at the beach, downtown, or on the river. There are historic reenactments, festivals and fairs, live concerts, and pirate parties, too. There's so many events to experience in St. Augustine that locals say, "it's a small town with a big calendar."

Today
May. 7

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

Staff Spotlight

St. Augustine Food + Wine Festival—2026

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

Sponsored Partners

Lightner Museum of St. Augustine

Dolphin Tours at Red Boat Tours

Sunset Cruises at Red Boat Tours

Ocean Sands Beach Boutique Inn

La Fiesta - Ocean Inn & Suites

La Fiesta - Ocean Inn & Suites

All St. Augustine Events

Thursday, May 7th, 2026

Live Music on Thursdays

Every Thursday

Restaurants and bars that offer live music on Thursdays throughout the year.

A cardboard British soldier from the Revolutionary War guards the entry to this exhibit

Florida at War: St. Augustine in the American Revolution

Wednesday, May 6, 2026 | 10:00 a.m. to 5:00 p.m.

Learn about St. Augustine during the Revolutionary War.

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

St. Augustine History Fest, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

St. Augustine hosts an annual history festival in May of 2026.

The stained-glass windows and chandelier in the First Congregation Sons of Israel in St. Augustine.

St. Augustine History Fest Tours, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

These historic properties offer free tours during one week in May.

Two storytellers in two photos

Romanza: Florida Stories by Florida Storytellers

Thursday, May 7, 2026 | 2:00 to 3:00 p.m.

Ambasador of Storytelling Award winners relate old and new Florida tales.

Wine and cheese on a table with an insert of an author signing a book

Romanza: Kim Bradley, Author—Wine and Cheese Event

Thursday, May 7, 2026 | 3:00 p.m. - 4:00 p.m.

Wine, cheese, and a discussion about the art of writing historical fiction.

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

St. Augustine Food + Wine Festival—2026

Wednesday, May 6 - Saturday, May 9, 2026 | Times and Locations Vary

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

George Thorogood and The Destroyers pose and perform on stage.

George Thorogood & The Destroyers at the St. Augustine Amphitheatre

Thursday, May 7, 2026 | 7:00 p.m. - 10:00 p.m.

Delivering raw, high-energy classics with unstoppable rock-and-roll swagger.

A large palm tree at sunset, leaning over the ocean surf

Limelight Theatre: Once on This Island

Thursday, May 7 - Sunday, May 24, 2026 | Times Vary

A popular Broadway musicial based on Hans Christian Anderson's Little Mermaid.

Joseph Arthur performs with his guitar.

Joseph Arthur at Cafe Eleven

Thursday, May 7, 2026 | 8:00 p.m. - 10:00 p.m.

A Grammy-nominated artist celebrated for the acclaimed album Big City Secrets.

Three rows of the Key of Seas student choir at Flagler College

Romanza Festivale: Key of Seas

Thursday, May 7, 2026 | 8:00 p.m. - 9:30 p.m.

Enjoy Flagler College's music ambassadors and a cappella ensemble.

Friday, May 8th, 2026

Live Music on Fridays

Every Friday

Restaurants and bars that offer live music on Fridays throughout the year.

A cardboard British soldier from the Revolutionary War guards the entry to this exhibit

Florida at War: St. Augustine in the American Revolution

Wednesday, May 6, 2026 | 10:00 a.m. to 5:00 p.m.

Learn about St. Augustine during the Revolutionary War.

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

St. Augustine History Fest, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

St. Augustine hosts an annual history festival in May of 2026.

The stained-glass windows and chandelier in the First Congregation Sons of Israel in St. Augustine.

St. Augustine History Fest Tours, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

These historic properties offer free tours during one week in May.

Sheet music covers from old baseball songs

Romanza: First Coast Opera—Baseball Music

Friday, May 8, 2026 | 12:00 p.m. to 1:00 p.m.

Opera vocalists present songs about America's favorite pastime—baseball.

Numerous reenactor groups standing at City Gate in St. Augustine.

Historic Timeline Saunter

Select Days, Feb. - Sep. | 5:30 p.m. to 8:30 p.m.

Local members of the Historic Florida Militia march through historic downtown.

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

St. Augustine Food + Wine Festival—2026

Wednesday, May 6 - Saturday, May 9, 2026 | Times and Locations Vary

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

Ethel Cain poses before a richly textured background.

Ethel Cain at The St. Augustine Amphitheatre

Friday, May 8, 2026 | 7:00 p.m. - 10:00 p.m.

Performing music that has captivated millions since her 2017 debut.

Two men with ball caps outside on a sunny day

A Classic Theatre: Rounding Third

Friday, May 1 - Sunday, May 10, 2026 | See Times Below

This two-man play portrays two Little League coaches and their season.

Romanza: St. Augustine Concert Band

Friday, May 8, 2026 | 7:30 p.m. - 9:00 p.m.

The Romanza Festivale presents the band's last concert of the season.

A large palm tree at sunset, leaning over the ocean surf

Limelight Theatre: Once on This Island

Thursday, May 7 - Sunday, May 24, 2026 | Times Vary

A popular Broadway musicial based on Hans Christian Anderson's Little Mermaid.

Kelp performs on stage with their guitars and drums.

Kelp with Outeredge & Graves B'Hamala at Cafe Eleven

Friday, May 8, 2026 | 8:00 p.m. - 10:00 p.m.

Surf-inspired grooves, energetic local rock, and psychedelic vibes collide for a dynamic night of genre-blending music.

Sam Bush clutches his guitar and performs on stage.

Sam Bush at Ponte Vedra Concert Hall

Friday, May 8, 2026 | 8:00 p.m. - 10:00 p.m.

Redefining acoustic music with virtuosic mandolin playing and a genre-bending spirit.

A stand up microphone on the Third Space Improv stage.

Romanza Festivale: Classic Comedy Night

Friday, May 8, 2026 | 8:00 p.m. - 10:00 p.m.

Showcasing local and regional stand up comedians on second Fridays.

Saturday, May 9th, 2026

Live Music on Saturdays

Every Saturday

Restaurants and bars that offer live music on Saturdays throughout the year.

A line of cars with the hood up

Cars & Caffeine

Second Saturday of the Month | 8:00 a.m. - 10:00 a.m.

Grab a coffee and marvel at various automobiles.

Piles of tomatoes of various colors

Sunflower & Tomato Soirée

Saturday, May 9, 2026 | 9:00 a.m. - 4:00 p.m.

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

The GTM Research Reserve hosts a family seining event on the second Saturday of each month.

GTM Research Reserve: Family Seining

Second Saturday of the Month | 9:00 a.m. - 11:00 a.m.

Families learn to cast a seine net to collect various fish and crab species.

A cardboard British soldier from the Revolutionary War guards the entry to this exhibit

Florida at War: St. Augustine in the American Revolution

Wednesday, May 6, 2026 | 10:00 a.m. to 5:00 p.m.

Learn about St. Augustine during the Revolutionary War.

Upcoming Featured Events

The stained-glass windows and chandelier in the First Congregation Sons of Israel in St. Augustine.

Today
May 7

St. Augustine History Fest Tours, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

These historic properties offer free tours during one week in May.

A photo of black youth at a dance in St. Augustine in the early 1900s

Today
May 7

In Our Glory: Black Joy in Jim Crow St. Augustine

Saturday, Jan. 10 - Sunday, Jun. 28, 2026 | 10:00 a.m. to 5:00 p.m.

View a photography exhibit depicting the Jim Crow era in St. Augsutine.

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

Today
May 7

St. Augustine History Fest, 2026

Wednesday, May 6 - Sunday, May 10, 2026 | Times and Locations Vary

St. Augustine hosts an annual history festival in May of 2026.

Two storytellers in two photos

Today
May 7

Romanza: Florida Stories by Florida Storytellers

Thursday, May 7, 2026 | 2:00 to 3:00 p.m.

Ambasador of Storytelling Award winners relate old and new Florida tales.

Wine and cheese on a table with an insert of an author signing a book

Today
May 7

Romanza: Kim Bradley, Author—Wine and Cheese Event

Thursday, May 7, 2026 | 3:00 p.m. - 4:00 p.m.

Wine, cheese, and a discussion about the art of writing historical fiction.

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

Today
May 7

St. Augustine Food + Wine Festival—2026

Wednesday, May 6 - Saturday, May 9, 2026 | Times and Locations Vary

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

Related categories

Cannon Firing at the Castillo de San Marcos

Featured Events

Musicians playing at the St. Augustine Celtic Festival

Festivals

A magician lights a straw man that is standing in his left palm

Live Entertainment

The composer faces the St. Augustine Community Chorus as they perform in the Cathedral Basilica of St. Augustine

Arts & Culture

People paddling kayaks toward the sunset in Guana

Sports & Outdoors

For Kids

Historical

Bright spring flowers decorate a building in Historic St. Augustine

Seasonal

Food

Local Things to Do

Fundraisers

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