Last September, if you lived anywhere near downtown St. Augustine, you already knew the drill. Starting the night of September 18, North Cordova Street closed from Orange Street to the parking garage entrance. By the following evening, West Castillo Drive closed eastbound from US-1. The historic downtown parking garage, the one most residents default to for anything south of the Bridge of Lions, went dark to the public until 5 a.m. on Monday, September 22. The reason was a single two-day ticketed concert at Francis Field, headlined by acts like Beabadoobee, Father John Misty and David Kushner on Saturday and the Teskey Brothers, Rilo Kiley and Gigi Perez on Sunday, that had grown into the marquee weekend of the Sing Out Loud Festival.
That weekend isn't happening this September. The St. Augustine Amphitheatre moved the ticketed Francis Field Showcase to May 2027, which means the single event that used to determine how you planned the back half of the month simply isn't on the calendar. What's left instead is smaller, more scattered, and free. If you're still mentally blocking out the third weekend of September the way you did in 2025, you're planning around a closure that isn't coming.
The month didn't get quieter. It got split three ways.
Sing Out Loud is celebrating its 10th anniversary by returning to the format it started with in 2016: free Local Artist Showcases spread across the city, no single ticketed centerpiece. Over 100 acts are playing 17 venues across three weekends, September 4 to 6, 11 to 13, and 18 to 20, presented by PNC Bank. That's the backbone of the month. But two other events are stacked on top of it, and they don't share Sing Out Loud's footprint at all.
Here's how the month actually breaks down:
| Weekend | What's happening | Where | Cost |
|---|---|---|---|
| Sept 4-6 | Sing Out Loud Local Artist Showcase (weekend 1) + 3rd Annual Aviles Street Festival | 17 venues citywide + Aviles Street | Free |
| Sept 11-13 | Local Artist Showcase (weekend 2), including Aoife O'Donovan at Spinster Abbott's and the Sam Grisman Project at Ponte Vedra Concert Hall | Same 17 venues | Free, one ticketed act |
| Sept 18-20 | Local Artist Showcase (weekend 3, closing) | Same 17 venues | Free |
| Sept 24-27 | St. Augustine Songwriters Festival + Sip Out Loud + St. Augustine Record Fair | Colonial Oak Music Park, Bin 39, St. Augustine Amphitheatre | Mostly free, Sip Out Loud ticketed |
Three different organizations are running three different events on overlapping weekends, and each one has its own geography. Sing Out Loud spreads thin across the whole city. The Aviles Street Festival is deliberately narrow, contained to a single block. The Songwriters Festival sits somewhere in between, anchored at Colonial Oak Music Park but pulling in a handful of other downtown rooms.
The Aviles Street weekend isn't a smaller version of the music festival. It's a different event entirely.
The Aviles Street Festival lands on Saturday, September 5, from noon to 9 p.m., which puts it inside the same window as Sing Out Loud's opening weekend. But treating it as a side stage of the music festival misses what it actually is. It's the third annual run of an event co-hosted by the Aviles Street Merchants Association and the Ximenez-Fatio House Museum, timed to Hispanic Heritage Month and landing three days before the city marks its 461st Founders Day on September 8.
The festival stays on one narrow, brick-paved corridor, a street old enough that the city points to it as the oldest platted street in the country. Expect flamenco performances from ZaZa Flamenca at The Bart on Aviles, sword-dueling demonstrations, plein air painters working live at the Ximenez-Fatio House Museum and Acacia Tree Gallery, and a festival BINGO card that sends visitors through participating merchant storefronts for a shot at a gift basket. Mini walking tours run out of The Bart on Aviles throughout the afternoon.
None of that requires the road closures or shuttle logistics that a Francis Field concert did. It's a single street, closed to through traffic for an afternoon, not a downtown-wide event. If your September plan has you avoiding Aviles Street the same way you'd avoid the parking garage during a big concert weekend, you're overcorrecting. The scale isn't comparable.
The showcase venues cluster into two pockets, not one sprawling map
Trying to hit all 17 Sing Out Loud venues in one night isn't realistic, and the schedule doesn't really ask you to. The venue list splits fairly cleanly into two walkable pockets.
Downtown core, roughly bounded by San Marco Avenue and the old city streets:
- Spinster Abbott's, 61 San Marco Avenue
- The Waterworks, 184 San Marco Avenue
- Colonial Oak Music Park, on St. George Street
- Trade Winds Lounge, 124 Charlotte Street
- Dog Rose Brewing Co., 77 Bridge Street
- Casa de Vino 57, on Treasury Street
Anastasia Boulevard cluster, across the Bridge of Lions:
- Sarbez!, 115 Anastasia Boulevard
- Shanghai Nobby's, 10 Anastasia Boulevard
- Hornski's Brewing Co., 100 Anastasia Boulevard
That split matters more than it looks. A resident who lives closer to the Anastasia Island side can spend an entire showcase weekend without crossing the bridge, catching sets at Hornski's, Sarbez!, and Shanghai Nobby's within a few blocks of each other. Someone on the downtown side has an equally dense night without leaving San Marco Avenue and the surrounding blocks. The festival isn't asking you to cover the whole city in one evening. It's really offering two separate, walkable nights depending on which side of the bridge you're starting from.
What the closing weekend actually adds up to
The final stretch, September 24 through 27, is where the calendar gets its last layer. The St. Augustine Songwriters Festival, now in its ninth year, brings Nashville songwriters into intimate downtown rooms, centered at Colonial Oak Music Park, for free performances built around the stories behind the songs rather than a standard concert set. Sing Out Loud closes out its own calendar the same week with a free Music Business Panel at Spinster Abbott's on September 23, a ticketed Sip Out Loud tasting event at Bin 39 on September 24, and the St. Augustine Record Fair, presented by Tonevendor Records, at the St. Augustine Amphitheatre on September 27.
Compare that to how the month ended in 2025, when the closing weekend meant the Francis Field ticketed concert and the parking and road closures that came with it. This year the closing weekend is a record fair, a songwriter showcase, and a wine tasting. Different scale, different footprint, different reason to be downtown.
The practical takeaway for anyone who already lives here
If you're weighing which weekends to build plans around, here's the shape of it. September 4 to 6 gives you a choice between the free, sprawling Sing Out Loud showcase or the contained, single-street Aviles Street Festival, both happening at the same time but occupying different corners of the city. September 11 to 13 and 18 to 20 are showcase weekends only, split across the two venue pockets described above. September 24 to 27 wraps the month with songwriter sets, a record fair, and one ticketed tasting event, all clustered downtown without the road and garage closures that defined the same week last year.
The one thing you don't need to plan around this year is the thing that used to define the month. No Francis Field weekend means no four-day parking garage closure, no rerouted STAR Circulator schedule, no West Castillo shutdown. If you're still bracing for that, you're bracing for an event that's on hold until May 2027.
Living in a town where the calendar rearranges itself every year is part of what makes St. Augustine worth staying in. Knowing which parts actually changed, and which parts just look the same from a distance, is the difference between a resident and a visitor working off last year's map.
If you're weighing a move within St. Augustine, or thinking about what your own property could be worth heading into fall, Ponte Vedra & Co. knows this market block by block. Request a free consultation and home valuation whenever you're ready to talk specifics.
