For nine years, if you lived in St. Augustine and wanted to catch Sing Out Loud, you circled one weekend. The festival's headline act played Francis Field, tickets moved fast, and everyone downtown knew exactly which Friday through Sunday to plan around. This September, that weekend did not exist. Organizers moved the marquee Francis Field showcase to May 2027, and what replaced it was not smaller so much as scattered: three weekends of free local shows spread across seventeen different rooms, scheduled alongside one of the fullest concert calendars the St. Augustine Amphitheatre has booked in years. Add a food-and-retail project on Old Moultrie Road that spent part of this year fighting the county over whether it was even allowed to operate, and you get a September with no single date to remember. Residents had to build their own calendars.
The Weekend That Isn't There Anymore
Sing Out Loud turns ten this year, and the anniversary is the reason for the change. Festival organizers announced that the event's largest single draw, the ticketed Francis Field weekend that brought in national headliners, is shifting to the third weekend of May starting in 2027. That means 2026 is the first year since the festival launched in 2016 that there is no Francis Field weekend at all.
What was scheduled instead was the Local Artist Showcase, with three consecutive weekends of free performances: September 4 through 6, September 11 through 13, and September 18 through 20. More than 100 performances were scheduled across those nine days, spread across seventeen venues around town, according to St. Johns County's own event listing. Add the St. Augustine Songwriters Festival, scheduled for September 24 through 27, and the St. Augustine Record Fair, scheduled for September 27, and the month adds up to more total programming than any single Francis Field weekend used to deliver. It did not arrive as one event you buy a ticket to. It was spread across bars, breweries, and small stages you had to already know about.
The venue list itself tells you something about how this town actually works after dark. Scheduled showcases included Sarbez! on Anastasia Boulevard, Shanghai Nobby's a few doors down, Trade Winds Lounge and Spinster Abbott's downtown, Colonial Oak Music Park on St. George Street, Dog Rose Brewing Co. on Bridge Street, Hornski's Brewing Co., and The Waterworks on San Marco Avenue. None of these are new to St. Augustine. What was new is that for one month, they were the whole festival, not just supporting acts to a headliner across town.
The Same Weeks, A Different Marquee
Here's the part that would surprise anyone assuming Sing Out Loud's smaller footprint means St. Augustine's live music scene is quieting down: the Amphitheatre's own fall lineup, running on largely the same calendar, is stacked with national names.
| Date | Act |
|---|---|
| Sept. 17 | Modest Mouse, with Robber Robber |
| Sept. 18 | John Fogerty & Steve Winwood: The Legacy Tour |
| Sept. 19 | Brad Paisley |
| Sept. 22-23 | James Taylor and His All-Star Band |
| Sept. 25 | Flipturn, with Winyah |
| Sept. 26 | Rise Against, with Alkaline Trio and Teen Mortgage |
| Sept. 27 | St. Augustine Record Fair, presented by Tonevendor Records |
| Sept. 29 | Of Monsters and Men |
| Oct. 1 | Sugarland, with Payton Sullivan |
Notice September 27. That's not a coincidence or a scheduling collision. The Record Fair is part of Sing Out Loud's own programming, held at the Amphitheatre itself, which means the festival's free, local-first identity and the venue's ticketed, national-act calendar actually share a single afternoon on the same lot at 1340C A1A South.
That overlap is the clearest evidence of what was happening this year. Sing Out Loud didn't get smaller because St. Augustine's appetite for live music shrank. It got smaller because the big-ticket version of that appetite moved next door, to a venue that already had a full slate booked. The town wasn't hosting less over the month; its schedule split the programming between a free, walkable, neighborhood format and a ticketed, single-address one, with the events overlapping across three weeks.
A Food Hall Fighting Its Way Back
The same "you have to know where to look" logic applies to where you'd eat before or after any of this. The Outpost at Old Moultrie, a planned retail and dining village built from repurposed shipping containers at 2505 Old Moultrie Road, spent part of this year closed after a dispute with St. Johns County over whether the property qualified as an "improved" commercial site. A special magistrate sided with the county, and the food trucks, vendors, and even a small airbrush art business operating there were ordered to stop.
Owners Justin and Jessica Tahilramani, a husband-and-wife team who moved to St. Johns County after careers in the military, have kept the project moving since. Fourteen container spaces at the nearly two-acre parcel were listed for lease through a local commercial brokerage as the couple worked toward a full buildout, and as of this spring the project was still targeting a third-quarter 2026 grand opening. One detail worth knowing if you're planning around it: the site's proximity to nearby churches complicates its ability to serve alcohol, and the ownership team has been pursuing a variance to allow it.
If you want to catch this one at its actual reopening rather than a projected date, the Tahilramanis have said the clearest updates come through the project's own Facebook and Instagram pages rather than any festival guide or countywide calendar. That's the same pattern as everything else this month. Nobody is aggregating this for you. You're the aggregator.
What This Actually Looks Like for Someone Living Here
If you were used to Sing Out Loud meaning one weekend, this September asked you to think in a completely different unit. Instead of clearing a Friday through Sunday in your calendar once, you had to check three separate weekends of showcases, a songwriters festival the following week, a record fair that closes it all out, and a concert calendar at the Amphitheatre that doesn't pause for any of it.
Practically, that meant picking your neighborhood and starting there. For the showcases, The Waterworks and Spinster Abbott's were both venues within a few blocks of each other near San Marco Avenue. On Anastasia Island, Sarbez! and Shanghai Nobby's were close enough to walk between sets. For people with Amphitheatre tickets during the showcase weekends, the free showcases offered something to do on the nights they didn't have tickets.
None of this is a complaint about the change. A ten-year-old festival evolving its format isn't a loss, and a fuller Amphitheatre calendar is its own kind of proof that the demand for live music here hasn't gone anywhere. What's true is that this year's schedule asked residents to piece together their own month rather than wait for one event to hand it to them. That's a different kind of St. Augustine September than the one most of us are used to. The lack of a single festival weekend didn't mean nothing was happening.
If you're new to the area and still learning which corners of town hold which kind of night out, or if you've been here for years and just want a local's read on how the season's actually shaping up, Martin Williams is always glad to talk through what's changing in St. Augustine and the rest of Northeast Florida. Let's Connect.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
