Don’t Miss These Exciting Events and Fall Festivals in St. Augustine FL
Planning one last hurrah before we hunker down and await the holidays? Fall in the Ancient City is full of exciting things to do! Whether you’re looking for lively music festivals, thrilling corn mazes, charming pumpkin patches, or educational cultural festivals, you’ll find it all right here.
If you’ve never been to St. Augustine, FL, in the off-season, you’re in for a treat. The mild temperatures make outdoor fun that much more enjoyable. And with fewer people, you can enjoy some of the best entertainment in the city without the hassle of crowds. You’ll also benefit from off-season rates when it comes to your vacation rental!
Whether you have a week or just a few days, be sure to take note of all the exciting festivals in St. Augustine, FL, this fall and see how many you can incorporate into your stay!
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Founders Day in St. Augustine
Celebrate the anniversary of the nation’s oldest city at the Founders Day celebration. Head to the Fountain of Youth Archaeological Park for a day of reenactments, weapons demonstrations, fun activities, and more!
Schedule of events:
- 10 AM: Reenactment of when the Spanish fleet first landed in 1565 (FREE)
- 11 AM: Catholic Mass at Rustic Altar on the Mission grounds (FREE - attendees are encouraged to bring a folding chair)
- 12 PM: Procession from mass to the Fountain of Youth
- 1 PM: Reenactment of the first Thanksgiving meal shared with the Timucuan tribe (Regular admission applies: $22.95 for adults, $9.95 for children 6-12, and free for those under 6)
- 1 PM – 5 PM: Encampment and weapons demonstrations at Fountain of Youth (Attendees will need to have purchased regular admission for this as well.)
When: September 6, 2025
Where: Fountain of Youth Archaeological Park
St. Augustine Songwriters Festival
This fall, the Annual St. Augustine Songwriters Festival returns with some of the biggest names in country music. Each night, multiple downtown venues will host award-winning writers as they play their songs in the round. Listen as they take turns sharing secrets from the writer’s rooms and reminisce on how some of your favorite radio hits were born.
Featured performers will include Rodney Clawson (“Sure Be Cool If You Did”, by Blake Shelton), Monty Criswell ("Just Fishin'", by Trace Adkins), Jon Nite ("Break Up in the End", by Cole Swindell), and many more.
Catch the performances at Prohibition Kitchen, Colonial Oak Music Park, Tradewinds Lounge, and St. Augustine Distillery.
When: September 26 - 28, 2025
Where: Various locations in downtown St. Augustine
Pumpkin Festival + Handmade Market
Wesley Wells Farm has the only pick-your-own pumpkin patch in St. Augustine. Visit the Pumpkin Festival this fall for family-friendly activities like hayrides, a petting zoo, kids' zone games, food trucks, and photo ops. You’ll also be able to shop handmade goods from local vendors and even pick your own veggies to add to your fall décor.
Tickets are $15 online or $18 at the gate, and the farm will be open from 9 AM to 5 PM.
When: September 27, 2025
Where: Wesley Wells Farm
Sykes Family Farms Corn Maze
One of the most popular St. Augustine October events is ready for another incredible season. The Sykes Family Farms “Cornfusing” corn maze opens October 5th and will operate Friday through Sunday until November 2nd.
This is one of the most exciting events in St. Augustine, so don’t miss out on your chance to experience the four levels of a-MAZE-ing fun. In addition to the maze at Sykes Family Farms, they’ll also have hay rides, playgrounds, a cow milking station, duck races, a cow train, farm animals, a barnyard ball zone, and glow-in-the-dark pumpkin blasters! Tickets are on sale now, so don’t wait to grab yours.
When: October 4 - November 2, 2025
Where: Sykes Family Farms
CroctoberFest Brew at the Zoo
Sip your way through the St. Augustine Alligator Farm when you visit the most popular conservation event of the year. Brew at the Zoo features samples from popular craft breweries, as well as food and live music. Enjoy tasty treats as you learn about coastal ecology and all the thrilling animals that make up our unique Florida ecosystem.
The price of entry funds continued research and public education events that help foster an understanding of crocodile behaviors and better species management.
The event will take place from 6 PM to 9 PM Saturday, October 4th, so grab your ticket before they’re sold out!
When: October 4, 2025
Where: St. Augustine Alligator Farm
Florida Bohemian Festival
The largest one-day vendor event in St. Augustine is taking place on October 5th at the Florida Agricultural Museum. Don’t miss Ancient City Entertainment’s Bohemian Festival, featuring art, food, yoga, live performances, and more. This festival is aimed at bringing the community together to celebrate and unify the mind, body, and spirit. Events and goods will center around holistic items, with workshops and activities on recycling, gardening, naturopathy, and self-improvement. General admission is $20, and kids 12 and under get in free.
When: October 5, 2025
Where: Florida Agricultural Museum
Greek Festival
The Annual St. Augustine Greek Festival is one of the top fall festivals in the city. This weekend of celebration highlights all the best parts of Greek culture. Enjoy live music, as well as dance troupes who will even be offering traditional folk dance lessons!
In addition to the live entertainment, you’ll indulge your taste buds in a variety of classic Greek dishes from spanakopita to baklava. Shop handmade and baked goods at the Agora (market) and find a perfect commemorative gift to take home. You’ll find everything from embroidered linens to hand-painted ceramics.
This event is the perfect opportunity to bring the family out and learn about a vibrant culture here in St. Augustine, so don’t miss out!
When: October 11 - 12, 2025
Where: Holy Trinity Greek Orthodox Church
St. Benedict Blues Festival
Dig into delicious gumbo and BBQ while you listen to fantastic blues music at the St. Benedict Blues Festival. Musicians from Northeast Florida and beyond will grace the stages at St. Benedict the Moor Catholic Church during their biggest fundraiser of the year.
Home-cooked food will be available each day, with a brunch on Sunday. Admission is only seven dollars, so bring the family and enjoy this unique St. Augustine event.
When: October 24-26, 2025
Where: Lincolnville Neighborhood in St. Augustine
Ancient City Kids Day
One of the best family events in St. Augustine is back and better than ever. Ancient City Kids Day is a free event featuring more than 40 youth organizations. Enjoy games, crafts, bounce houses, giveaways, contests, and live entertainment all day.
When: October 25, 2025
Where: Francis Field
Trick-or-Treating on St. George Street
In town for Halloween? Be sure to take the kids to St. George Street from 1 PM - 4 PM for a night of trick-or-treating in the historic district. Participating locations will be marked with balloons or signs, and all costumed children are invited to stop by for Halloween fun.
A photographer will be on-site to capture pictures of your family, so be sure to dress to impress! This free activity is sure to be a highlight of your fall vacation to St. Augustine.
When: October 25, 2025
Where: Historic District along St. George Street
Book Your Fall Getaway Directly with Coastal Realty
As you can see, this time of year is full of things to do, and these events just scratch the surface. For even more options, view our entire events list to see everything happening in town during your specific travel dates. But before you can plan your activities or buy your event tickets, you need to secure your vacation rental!
At Coastal Realty, we have the perfect St. Augustine beach house rentals for you. Whether you want an oceanfront property or you’re bringing Fido and need a pet-friendly rental, you’ll find it all when you browse our available vacation rentals. Remember to book your stay directly with Coastal Realty for the best rate, and discover why we’re the 2025 Official Community Choice Award-winning team in St. Augustine.
Frequently Asked Questions about Fall Festivals in St. Augustine, FL
Is October a good time to visit St. Augustine?
Yes! October is a great time to visit St. Augustine. Not only is there a ton to do, like ghost tours, free trick-or-treating for the kiddos, festivals, and more. But you'll also benefit from shoulder season discounts on vacation rentals and fewer crowds. You can't beat that!
What's the weather like in St. Augustine in October and November?
St. Augustine weather in October is slightly cooler, with highs in the upper 70s and lows in the mid-60s. St. Augustine weather in November is similar but slightly cooler, with highs around 73 and lows in the mid-50s.
Is St. Augustine a good fall break destination?
Yes! With exciting educational events like the Founder's Day Festival and the Greek Festival, as well as fun activities like family-friendly ghost tours and trick-or-treating opportunities, kids (and parents) will have a blast in St. Augustine on fall break.
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