Things to Do in St. Augustine in September 2026: Festivals, Concerts & Local Events

September is shaping up to be another busy month in St. Augustine, Florida, with live music, historic celebrations, festivals, outdoor events, and plenty of reasons to get out and enjoy the community.

Whether you're a local looking for weekend plans, visiting Florida's Historic Coast, or considering a move to the area, here's a look at some of the best St. Augustine events happening in September 2026.

Sing Out Loud Music Festival 2026

September 4 – 27 | Various Locations

September means the return of one of St. Augustine's signature music events: the Sing Out Loud Music Festival.

Celebrating its 10th anniversary in 2026, Sing Out Loud will feature more than 100 local and regional artists performing at venues throughout St. Augustine. The Local Artist Showcases take place during the first three weekends of September, with performances spanning everything from indie and country to jazz, hip-hop and more.

There's an important change this year for anyone familiar with the festival. The large Live Wildly Showcase at Francis Field will not take place in September. That marquee event is moving to May 2027, while September's programming focuses on local and regional performers, special events and the St. Augustine Songwriters Festival (more on that below).

Many of the performances are free, making this one of the best opportunities of the year to experience St. Augustine's local music scene.

First Coast Opera: Something's Brewing

September 10 & 12

First Coast Opera brings another unique performance to St. Augustine with Something's Brewing.

It's a great addition to September's arts calendar and offers something a little different for those looking to enjoy live performance beyond the month's festivals and larger concerts.

9/11 Ceremony of Remembrance

September 11 @ 8:30am

This year's 9/11 Ceremony of Remembrance in St. Augustine carries special significance as the country marks the 25th anniversary of September 11, 2001. 

The annual ceremony provides an opportunity for the St. Augustine community to come together to remember those who lost their lives and honor the first responders, service members, and families affected by the attacks.

Blackbeard's Pirate Ball

September 11

For something completely different, the Blackbeard's Pirate Ball returns for an evening inspired by St. Augustine's long maritime history.

Hosted by the Ancient City Privateers, the event brings plenty of pirate-themed fun to America's oldest city and is one of the more unique events on the September calendar.

Founder's Day 2026

September 12

You can't talk about events in St. Augustine without celebrating its history. Founder's Day commemorates the founding of St. Augustine by Pedro Menéndez de Avilés in 1565. As the nation's oldest continuously occupied European-established settlement, St. Augustine has a story unlike anywhere else in the country.

Founder's Day offers residents and visitors an opportunity to experience that history and learn more about the people and events that shaped the city.

Old City Home & Garden Expo

September 12

Homeowners, gardeners, and anyone looking for ideas for their next project should check out the Old City Home & Garden Expo.

The event brings together home improvement professionals, products, services, landscaping inspiration, and ideas for improving indoor and outdoor living spaces.

For St. Augustine homeowners, it's a timely opportunity to gather ideas before Florida's cooler fall weather arrives.

Tunnel to Towers 5K

September 12

The Tunnel to Towers 5K brings the community together to honor the sacrifices of first responders and military service members.

Taking place the weekend of the 25th anniversary of 9/11, this year's event should be particularly meaningful for participants and spectators alike.

Aqua East Grom Fest

September 18 & 19

It wouldn't be a St. Augustine events calendar without something happening at the beach.

The Aqua East Grom Fest celebrates the area's surf culture and gives young surfers an opportunity to compete and showcase their skills.

For local families and anyone who loves the beach lifestyle, it's a fun reminder of how closely St. Augustine's identity is tied to the ocean.

St. Augustine Heritage Book Festival

September 19

Book lovers can spend the day celebrating authors, stories, and local culture at the St. Augustine Heritage Book Festival.

The festival adds a literary component to an already diverse September calendar and is a great option for anyone interested in books, history, and the arts.

Estuary Fest 2026

September 19

One of September's best events for nature lovers is Estuary Fest 2026.

St. Johns County is surrounded by an incredible network of rivers, marshes, estuaries, and coastal ecosystems. Estuary Fest celebrates that natural environment while helping residents and visitors learn more about the waterways and wildlife that make Northeast Florida so special.

Frozen Banana Race

September 20

Runners have another reason to get outside with the Frozen Banana Race, featuring a 5K, 10K and Fun Run.

Whether you're chasing a personal best or simply looking for an active family event, this is another fun addition to the September calendar.

St. Augustine Songwriters Festival

September 24 - 27

The month closes out with one of my favorite concepts in St. Augustine's music calendar: the St. Augustine Songwriters Festival.

The four-day festival brings Nashville songwriters to multiple stages around St. Augustine for intimate performances that put the stories behind the songs front and center.

Unlike a traditional concert, these performances give audiences a chance to hear the people who actually wrote songs performed by some of country music's biggest artists. The festival is also part of the broader Sing Out Loud celebration.

Sip Out Loud

September 24

Also taking place on September 24 is Sip Out Loud, a wine and cultural event celebrating St. Johns County through food, wine, music, and art.

It's a great option for anyone looking for an evening event that combines local culture with St. Augustine's growing culinary scene.

Ancient City Con 2026

September 25 - 27

Pop culture takes over the final weekend of the month with Ancient City Con.

The multi-day convention celebrates comics, gaming, cosplay, collectibles, and entertainment, bringing a completely different type of festival experience to the St. Augustine area.

Pumpkin Festival & Handmade Market

September 26

It may still feel like summer outside, but fall officially starts showing up in St. Augustine with the Pumpkin Festival & Handmade Market.

Expect a seasonal atmosphere, handmade goods, local vendors, and plenty of fall inspiration as we head toward October.

Concerts for a Cause: Jackson Dean

September 26

Country music fans can catch Jackson Dean as part of the Concerts for a Cause series.

It's another example of just how much live music is packed into St. Augustine and St. Johns County during September.

Art & Bark in the Park

September 27

September wraps up with Art & Bark in the Park, combining local art with a dog-friendly community atmosphere.

For pet owners and local art supporters, it's a relaxed way to spend a Sunday and close out a packed month of events.

Big September Concerts at the St. Augustine Amphitheatre

September is also a huge month for live music at the St. Augustine Amphitheatre, with several nationally known artists coming to town.

Highlights include:

Modest Mouse – September 17
The Grammy-nominated alternative rock band brings its distinctive sound to The Amp.

Brad Paisley – September 19
One of country music's most recognizable performers takes the stage for a Saturday night show.

James Taylor – September 22 & 23
The legendary singer-songwriter and Rock & Roll Hall of Fame inductee brings two nights of his timeless catalog to St. Augustine.

Flipturn – September 25
The Florida-born indie rock band returns for a hometown-state performance.

Rise Against – September 26
The acclaimed punk rock band takes over The Amp for one of the month's higher-energy shows.

Of Monsters and Men – September 29
The Icelandic indie-folk band closes out the September Amphitheatre calendar with its signature blend of folk, rock, and atmospheric pop.

The Bottom Line

September is one of those months that shows exactly why there's always something to do in St. Augustine and St. Johns County.

It's also a great snapshot of what makes living in St. Augustine special. The city manages to combine its centuries of history with beaches, live music, arts, food, and a strong sense of community in a way that's difficult to replicate anywhere else in Florida.

For an updated calendar throughout the year, visit my St. Augustine Local Events page for more upcoming festivals, concerts, community events, and things to do around St. Augustine and St. Johns County.