See all St. Augustine, Florida has to offer. Visit the Nation’s Oldest City.

St. Augustine, the nation’s oldest city, also holds the distinction of being one of the nation’s most charming. Whether you’re a longtime resident or visiting the area for the first time, we’ve gathered all the resources you need to find where to stay, what to do and other community information about our unique little village.

Open Businesses, Restaurants, & More – Learn More »

Entertainment

  1. Events
  2. Entertainment

Events Search and Views Navigation

Event Views Navigation

Today

Recurring

Ancient City Con 2024

World Golf Village Renaissance St. Augustine Resort 500 South Legacy Trail, St. Augustine, FL, United States

Ancient City Con 2024 returns on September 13-15 at World Golf Village Renaissance St. Augustine Resort.  You won't want to miss Northeast Florida's longest running, multi-day, pop-culture convention experience. Featuring Celebrity Guests from your Favorite Shows along with ..... * Comic Artists * Cosplayers * Table Top and Video Gaming * Authors * Vendors * [...]

Prices Vary
Featured Featured Recurring

Sing Out Loud Festival 2024

Join us in St. Augustine for the 8th annual Sing Out Loud Festival 2024!   Live music performances at multiple venues on weekends in September.  Featuring performances by local, regional and national acts!  And ... many of the events are Free! The big events requiring a ticket purchase include: * Live Wildly Showcase at Francis Field [...]

Most are Free
Recurring

The Beetlejuice Pub Crawl

The Tasting Tours 88 Riberia Street, Suite #250, St. Augustine, FL, United States

The Beetlejuice Pub Crawl Please Note:  In light of Hurricane Milton, we will be closed on Wednesday and Thursday, October 9 and 10, 2024 for all tour activity, prioritizing the safety of our team and guests. We hope to resume normal tour activity on Friday, October 11, 2024.  Calling all Beetlejuice fans!  It's Showtime!!!  Brace [...]

$85.00
Featured Featured

Amy Steinberg Live!

CSL First City Parking Lot 93D Orange St., St. Augustine, FL, United States

Get Ready to Rock the Block with CSL First City when they kick off their inaugural Fundraiser and Block Party with the soulful sounds of New Thought recording artist Amy Steinberg .... Live on the porch at 93D Orange Street! When:  Friday, September 13, 2024 -- 7:00pm-10:00pm Come experience the heart and soul of CSL [...]

Donation
Recurring

Music at Colonial Oak Music Park

Colonial Oak Music Park 21 St George St, St. Augustine, FL 32084, st. augustine

September finds the Music at Colonial Oak Music Park is mostly under the Sing Out Loud Festival 'umbrella'.  Live music performances by local, regional, and national acts Friday - Sunday, September 6-22, 2024.   Followed by the St. Augustine Songwriters Festival featuring today’s hottest hit songwriters, the legends of yesterday and the stars of tomorrow ... [...]

Free Admission
Recurring

Ancient City Con 2024

World Golf Village Renaissance St. Augustine Resort 500 South Legacy Trail, St. Augustine, FL, United States

Ancient City Con 2024 returns on September 13-15 at World Golf Village Renaissance St. Augustine Resort.  You won't want to miss Northeast Florida's longest running, multi-day, pop-culture convention experience. Featuring Celebrity Guests from your Favorite Shows along with ..... * Comic Artists * Cosplayers * Table Top and Video Gaming * Authors * Vendors * [...]

Prices Vary
Recurring

Historic Weapons Demonstrations

Castillo de San Marcos 1 South Castillo Dr, St. Augustine, FL, United States

Be sure to check out the Historic Weapons Demonstrations at the Castillo de San Marcos National Monument … every week on Saturday and Sunday!  Join park staff and volunteers (usually dressed in period garb). Demonstrations are usually on the Castillo’s gundeck and last approximately 15 minutes.  Occasionally, they take place on the grounds outside of [...]

Park Entry Fee
Recurring

The Beetlejuice Pub Crawl

The Tasting Tours 88 Riberia Street, Suite #250, St. Augustine, FL, United States

The Beetlejuice Pub Crawl Please Note:  In light of Hurricane Milton, we will be closed on Wednesday and Thursday, October 9 and 10, 2024 for all tour activity, prioritizing the safety of our team and guests. We hope to resume normal tour activity on Friday, October 11, 2024.  Calling all Beetlejuice fans!  It's Showtime!!!  Brace [...]

$85.00
Featured Featured Recurring

Sing Out Loud Festival 2024

Join us in St. Augustine for the 8th annual Sing Out Loud Festival 2024!   Live music performances at multiple venues on weekends in September.  Featuring performances by local, regional and national acts!  And ... many of the events are Free! The big events requiring a ticket purchase include: * Live Wildly Showcase at Francis Field [...]

Most are Free
Recurring

Music at Colonial Oak Music Park

Colonial Oak Music Park 21 St George St, St. Augustine, FL 32084, st. augustine

September finds the Music at Colonial Oak Music Park is mostly under the Sing Out Loud Festival 'umbrella'.  Live music performances by local, regional, and national acts Friday - Sunday, September 6-22, 2024.   Followed by the St. Augustine Songwriters Festival featuring today’s hottest hit songwriters, the legends of yesterday and the stars of tomorrow ... [...]

Free Admission
Go to Top