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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."

Wednesday
May. 6

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

Beacher's Lodge - Oceanfront Suites

Beacher's Lodge - Oceanfront Suites

Ocean Sands Beach Boutique Inn

All St. Augustine Events

Monday, May 18th, 2026

Live Music on Mondays

Every Monday

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

Students in black showcase clothes pose under the yes and sign

Level 1 Improv: Improv Basics for Grown-Ups

Monday, May 4 - Monday, Jun. 15, 2026 | 6:30 to 9:00 p.m.

Third Space Improv hosts a six-week improv class for beginners.

Tuesday, May 19th, 2026

Live Music on Tuesdays

Every Tuesday

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

Songwriters Night in St. Augustine

St. Augustine Songwriters Night

Monthly, on Third Tuesdays | 6:00 p.m. - 8:00 p.m.

Each month, four local songwriters share their stories and songs.

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.

Wednesday, May 20th, 2026

Live Music on Wednesdays

Every Wednesday

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

A wooded trug carried by a woman with filled with fresh herbs and fruits

Wednesday Pier Farmers Market

Every Wednesday | Times Vary

Support local farmers, makers, and artists and take a walk on the beach.

West King Street Wednesdays located in St. Augustine, FL.

West King Wednesdays

Third Wednesdays, Feb. - Dec. | 10:00 a.m. - 10:00 p.m.

West King Street hosts pop-up markets, live music, and fun on third Wednesdays.

People lounging on the sand enjoying live music

Music and Art by the Sea 2026

Select Summer Wednesdays | 3:00 p.m. - 9:00 p.m.

Enjoy an art exhibition and local musicians at the pier in the summer.

The raggae artist, Protoje, sitting on stone steps surrounded by palms

Protoje at Colonial Oak Music Park

Wednesday, May 20, 2026 | 6:00 p.m. to 10:00 p.m.

Blending reggae with hip-hop, jazz and soul to appeal to several generations.

Archer taking aim with a recurve bow

Military Veteran Archery

Select Third Wednesdays | 7:15 p.m. to 8:30 p.m.

Take aim and connect with other veterans.

Thursday, May 21st, 2026

Live Music on Thursdays

Every Thursday

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

A container of wine bottles at an outdoor event

St. Augustine Wine Walk

On the third Thursday of most months | 6:00 p.m. - 8:00 p.m.

Casa de Vino 57 hosts a wine walk and tasting around historic downtown.

A painting by Augusto Ferrer-Dalmau showing Bernardo de Gálvez at the Siege of Pensacola

Unknown Florida in the American Revolution

Monthly, Jan. - May, 2026 | 6:30 p.m. to 8:30 p.m.

Learn how events in Florida impacted the American Revolution at this lecture series.

Willie Nelson grips his guitar, gazing ahead in quiet reflection.

Willie Nelson and Family at The St. Augustine Amphitheatre

Thursday, May 21, 2026 | 7:30 p.m. - 10:00 p.m.

Country music trailblazers showcase timeless hits.

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.

Mike Tramp smiles and poses in front of a bright yellow backdrop.

Mike Tramp at Cafe Eleven

Thursday, May 21, 2026 | 8:00 p.m. - 10:00 p.m.

Delivering a high-energy blend of hard rock, glam, metal, and pop rock.

Friday, May 22nd, 2026

Live Music on Fridays

Every Friday

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

Blue Crab Festival 2026

Friday, May 22 - Sunday, May 24, 2026 | Times Vary

Eat delicious seafood with the company of live music and family activities.

A painting of a young woman from the 1500s standing in an archway

All the Devils Shakespeare: Much Ado About Nothing

Friday and Saturday, May 22 - 23, 2026 | 7:00 p.m. to 9:00 p.m.

A local theatre company focusing on classic plays, presents a Shakespeare comedy.

Tim Meadows stands in a phone booth and poses for fans.

Tim Meadows at Ponte Vedra Concert Hall

Friday, May 22, 2026 | 7:30 p.m. - 10:00 p.m.

An Emmy-nominated comedian brings his sharp wit and iconic charm to the stage.

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.

A stand up microphone on the Third Space Improv stage.

Smart Women in Comedy

Friday, May 22, 2026 | 8:00 p.m. - 10:00 p.m.

Smart, female comedians take the spotlight at Third Space Improv.

A Night Under the Stars

Friday, May 22, 2026 | 8:30 p.m. to 10:00 p.m.

Experience the wonders of the cosmos.

Saturday, May 23rd, 2026

Live Music on Saturdays

Every Saturday

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

Cars and Coffee photo for Classic Car Museum of St. Augustine

Cars & Coffee

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

Share your love for coffee and classic cars.

Visitors strolling through the local vendors tents

Amphitheatre Farmers Market

Saturdays | 8:30 a.m. to 12:30 p.m.

Enjoy fresh local produce, handmade arts and crafts, and live entertainment.

Volunteers picking up trash on the beach

GTM Reserve Beach Cleanup

Fourth Saturdays Monthly | 9:00 a.m. - 11:00 a.m.

Join the GTM Research Reserve's monthly beach cleanup.

Cannon Firing at the Castillo de San Marcos

Weekend Cannon Firing

Saturdays and Sundays | 10:30 & 11:30 a.m., and 1:30, 2:30, & 3:30 p.m.

Be a part of history at the Castillo de San Marcos every weekend.

Blue Crab Festival 2026

Friday, May 22 - Sunday, May 24, 2026 | Times Vary

Eat delicious seafood with the company of live music and family activities.

Upcoming Featured Events

A ballerina leaping in the performance, "Rapunzel"

Friday
May 15

St. Augustine Ballet: "Rapunzel"

Friday, May 15 & Saturday, May 16, 2026 | Times Vary

Experience the tale of a trapped girl in a tower awaiting freedom and love.

Friday
May 15

Romanza: St. Augustine Orchestra Spring Concert

Friday, May 15, 2026 | 7:30 p.m. - 9:00 p.m.

The orchestra brings Broadway to town for their final concert of the season.

Echo Piano Duo performing on one piano in a four-hand compostion

Friday
May 15

Romanza Festivale: The Echo Piano Duo

Friday, May 15, 2026 | 7:30 p.m. to 9:00 p.m.

These pianists "doctors" have performed at home and abroad.

Wine flutes with white and red wines and a tray of breads, olives, and cheese

Saturday
May 16

Romanza Festivale: A Taste of Italy

Saturday, May 16, 2026 | 4:00 p.m. to 6:30 p.m.

Slow down and savor Italian flavors, art by diverse artists, and community connections.

An organized dinner inside The Venue

Saturday
May 16

Slow Food USA Presents A Joyful Dinner

Saturday, May 16, 2026 | 5:30 p.m. - 8:30 p.m.

A dining experience featuring a three-course dinner from a local chef.

Bruce Forman and Pat Bergeson on stage playing guitars

Saturday
May 16

A Gamble Rogers Concert: Pat Bergeson & Bruce Forman

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.

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.