St. Johns County's Fall Festival Calendar: Sing Out Loud Changes, Cracker Day Returns

Where did the big Saturday night show at Francis Field go this year?

If you went looking for it, the ticketed national-act lineup that Sing Out Loud has built its September reputation on in recent years, you didn't find one advertised for 2026. That's not a scheduling gap. According to Visit St. Augustine's own event listing, the multi-day showcase that once brought acts like Beabadoobee, Vance Joy, Hozier and Father John Misty to Francis Field has been pulled out of September entirely and moved to May 2027. For its 10th anniversary, Sing Out Loud went the other direction: smaller stages, no ticket, no single headliner.

The Show That Didn't Come Back

Last September, the festival's marquee weekend at Francis Field functioned almost like a separate event bolted onto the free local showcase, drawing acts from well outside Northeast Florida. This year that piece is gone from the September calendar, with the next Francis Field showcase not scheduled until next spring. What's left in its place is the format the festival launched with back in 2016: free, local, and spread across the city rather than concentrated on one field.

That's worth knowing if you've filed Sing Out Loud away as "the concert with the big names" and skipped it in past years because you didn't want to buy a ticket. This year there wasn't one to buy.

What Took Its Place

In its 10th year, Sing Out Loud ran more than 100 acts across 17 venues over three weekends, September 4-6, 11-13 and 18-20, all free to attend. The festival is produced by SJC Cultural Events, the same nonprofit that runs the St. Augustine Amphitheatre and the Ponte Vedra Concert Hall, and this year it leaned into the parts of the city most locals already have on their regular rotation:

• Colonial Oak Music Park
• Spinster Abbott's
• Shanghai Nobby's
• Dog Rose Brewing Co.
• Hornski's Brewing Co.
• Sarbez!
• Ragga Surf Cafe
• Boat Drinks
• Casa de Vino 57
• The Waterworks
• Trade Winds Lounge

A few of the free bookings punched well above what "local showcase" usually implies. Grammy-winning singer-songwriter Aoife O'Donovan played a free set at Spinster Abbott's on September 11, and Nashville mandolin player Jarrod Walker performed September 5 under a free ticket lottery. The festival's programming didn't stop with music, either. A Sing Out Loud Music Business Panel ran September 23 at Spinster Abbott's, the St. Augustine Songwriters Festival brought Nashville songwriters to Colonial Oak Music Park and other downtown spots from September 24 through 27, and the St. Augustine Record Fair, presented by Tonevendor Records, closed things out at the Amphitheatre on the 27th. A ticketed one-off called Sip Out Loud ran September 24 at Bin 39 for anyone who wanted something a little more curated than a bar crawl.

None of this required a festival wristband. It required knowing which Friday, Saturday or Sunday to show up and which door to walk through.

Then The County Changes Its Clothes

Once the Record Fair wraps on September 27, the downtown music circuit goes quiet for less than a week before the fall calendar picks back up somewhere else entirely. Croctober Fest, a beer-tasting event at the St. Augustine Alligator Farm, runs October 3. The St. Augustine Greek Festival takes over Holy Trinity Greek Orthodox Church October 11 and 12. That same Sunday, the Woman's Exchange of St. Augustine hosts Artisans in the Garden at the Peña-Peck House from noon to 4:30, free admission, and St. Augustine Ballet performs Dracula at Lewis Auditorium on the Flagler College campus.

The Pumpkin Patch at St. Augustine Shores United Methodist Church opens October 12 and runs through the end of the month. On October 15, the Harvest Hoedown at Tringali Barn runs from 5 to 9 p.m. to benefit Pie in the Sky St. Johns. Parker Flower Farms opens for farm days starting October 17 and continuing through November 22.

Here's the useful version of all of it in one place:

Cracker Day Returns for Its 67th Year

Right in the middle of that stretch, on October 10, sits Cracker Day. This is the 67th annual running of the event, hosted by the St. Johns County Cattlemen's Association at the fairgrounds in Elkton.

The name refers to the original Florida cowboys, who herded cattle descended from stock the Spanish brought over centuries ago, using the crack of a whip rather than a lasso. Gates open at 6 a.m. for competitors, the farmers market and general activities start around 9, and the whole thing wraps by 6 p.m. Admission is five dollars per vehicle, cash only, the same price it's been for years. If you want to camp on the grounds, that's another twenty-five dollars a night. The farmers market runs 9 to 4 with datil pepper sauces, local honey and handmade wooden furniture, and the day includes horse races, whip-cracking demonstrations and a petting zoo alongside barbecue and kettle corn.

There's no app, no lineup announcement, no ticketed VIP tier. The Cattlemen's Association has run the festival since the 1950s, at the fairgrounds off State Road 207.

That contrast is really the point of looking at this calendar at all. Sing Out Loud's 10th-anniversary September program featured free, hyperlocal programming across a dozen-plus small venues, while the ticketed Francis Field showcase moved to May 2027. Out at the fairgrounds in Elkton, Cracker Day remains a fixture on the October calendar.

If you're weighing whether to spend a Saturday out at the fairgrounds or a Sunday on San Marco Avenue this October, you don't have to choose just once. Both calendars run the same week. Cracker Day charges $5 per vehicle; the St. Augustine events listed here for Sunday are on October 11.

For more on life across St. Johns County's neighborhoods, from downtown St. Augustine to the coastal corridors nearby, The Real Jacksonville keeps a running local guide worth bookmarking.