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Drinks & Music

Tuesday, May 12th, 2026

Dance partners performing the cha-cha

Cha-Cha Dancing at Arnold's Lounge

Tuesdays, May 5 - 26, 2026 | 6:30 p.m. - 10:00 p.m.

Have a lively and playful time learning this Cuban dance form.

Friday, May 15th, 2026

A vampire removes his mask, revealing his blood red eyes.

Blade Rave at Cafe Eleven

Friday, May 15, 2026 | 8:30 p.m. - 10:30 p.m.

A high-energy, vampire-inspired night of techno, EDM, goth, and house.

Saturday, May 16th, 2026

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.

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

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.

Sean Chambers performs live on stage with his guitar.

Sean Chambers at Cafe Eleven

Saturday, May 16, 2026 | 8:00 p.m. - 10:00 p.m.

Bringing his fiery guitar work and soulful sound to a high-energy performance packed with fan-favorites.

Sunday, May 17th, 2026

Jason Ricci plays the harmonica on stage with The Bad Kind music band.

Jason Ricci & The Bad Kind at Cafe Eleven

Sunday, May 17, 2026 | 8:00 p.m. - 10:00 p.m.

Blending harmonica melodies with contemporary alternative rock.

Tuesday, May 19th, 2026

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.

Dance partners performing the cha-cha

Cha-Cha Dancing at Arnold's Lounge

Tuesdays, May 5 - 26, 2026 | 6:30 p.m. - 10:00 p.m.

Have a lively and playful time learning this Cuban dance form.

Wednesday, May 20th, 2026

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

West King Wednesdays

Third Wednesdays | 10:00 a.m. - 10:00 p.m.

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

Thursday, May 21st, 2026

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.

Friday, May 22nd, 2026

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.

Saturday, May 23rd, 2026

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.

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.

Sunday, May 24th, 2026

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.

Tuesday, May 26th, 2026

Dance partners performing the cha-cha

Cha-Cha Dancing at Arnold's Lounge

Tuesdays, May 5 - 26, 2026 | 6:30 p.m. - 10:00 p.m.

Have a lively and playful time learning this Cuban dance form.

Wednesday, May 27th, 2026

Bandmates from The Cold Stares pose in front of a bar.

The Cold Stares At Cafe Eleven

Wednesday, May 27, 2026 | 8:00 p.m. - 10:00 p.m.

Blending rock and blues while taking fans on an audio journey.

Thursday, May 28th, 2026

Terrance Simien beams as he stands before a scenic bayou backdrop.

Terrance Simien and The Zydeco Experience at Cafe Eleven

Thursday, May 28, 2026 | 8:00 p.m. - 10:00 p.m.

Igniting the vibrant spirit of Creole Zydeco with a Grammy-winning legacy.

Saturday, May 30th, 2026

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.

Tuesday, June 2nd, 2026

Dance partners performing the cha-cha

Cha-Cha Dancing at Arnold's Lounge

Tuesdays, May 5 - 26, 2026 | 6:30 p.m. - 10:00 p.m.

Have a lively and playful time learning this Cuban dance form.

Chris Duarte sits on a barstool and strums his guitar.

Chris Duarte at Cafe Eleven

Tuesday, Jun. 2, 2026 | 8:00 p.m. - 10:00 p.m.

Thrilling audiences with his high-voltage performances and signature blues-rock sound.

Saturday, June 6th, 2026

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.

Wednesday, June 10th, 2026

Musician Kyle Smith playing guitar instage, outside

Kyle Smith at Cafe Eleven

Wednesday, Jun. 10, 2026 | 8:00 p.m. - 10:00 p.m.

Fusing reggae, rock, ska and punk into a distinctly Southern California sound.

Saturday, June 13th, 2026

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.

Sunday, June 14th, 2026

Gary Hoey strums his guitar while wearing black sunglasses.

Gary Hoey at Cafe Eleven

Sunday, Jun. 14, 2026 | 8:00 p.m. - 10:00 p.m.

Blending electrifying riffs into a one-of-a-kind performance.

Tuesday, June 16th, 2026

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.

Joanna Connor wears a knitted hat and poses with her guitar in front of an orange backdrop.

Joanna Connor at Cafe Eleven

Tuesday, Jun. 16, 2026 | 8:00 p.m. - 10:00 p.m.

Providing a fiery voice and a power-charged performance for blues fans.

Wednesday, June 17th, 2026

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

West King Wednesdays

Third Wednesdays | 10:00 a.m. - 10:00 p.m.

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

Thursday, June 18th, 2026

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.

Chris Cain smiles and sings with his guitar in front of a black backdrop.

Chris Cain At Cafe Eleven

Thursday, Jun. 18, 2026 | 8:00 p.m. - 10:00 p.m.

A distinguished blues artist, known for soulful guitar licks and refined lyrics.

Friday, June 19th, 2026

Jimmie "JJ" Walker smiles in front of a blue backdrop.

JIMMIE “JJ” WALKER at Cafe Eleven - CANCELLED!

Friday, Jun. 19, 2026 | 7:30 p.m. - 10:00 p.m.

A celebrated comedian, known for a style that audiences still call Dyn-o-mite!

Related categories

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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

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Sports & Outdoors

For Kids

Historical

Bright spring flowers decorate a building in Historic St. Augustine

Seasonal

Food

Local Things to Do

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