Fun Fall Events in St. Augustine
With the weather starting to cool, humidity dropping and quiet, less crowded beaches and brick-paved streets, Fall in St. Augustine is quite possibly the best time of year. At Florida Water Tours, we love getting out on the water to enjoy an earlier sunset and we love getting out on the town for all the exciting fall events.
September
Sing Out Loud Festival – All September long!
For the ninth year in a row, St. Augustine will host one of the biggest music festivals in the Southeast, the Sing Out Loud Festival, where every Friday, Saturday and Sunday in the month of September, live music and entertainment will be strewn all over town. From local musical acts to national headliners, Sing Out Loud brings together a unique blend of music and most of it is free. The Lively Wildly Showcase is the only for-sale ticketed event, hosted on Saturday, September 20th and Sunday, September 21st, with headliners like Father John Misty, Hozier, The Teskey Brothers, Rilo Kiley and so many more! Read more about this amazing fest on our blog.
2025 Pumpkin Festival & Handmade Market – Saturday, September 27, 2025 from 9AM to 5PM
Wesley Wells Farms presents their annual fall festival, with food trucks, live entertainment and handmade craft vendors. Pick your own pumpkin, cruise through a crop maze and sunflower field, hitch a hay ride, meet farm animals and so much more. They’ll have fresh produce and yummy baked goods, and a market filled with hand-crafted items. It’s a fun-filled day for all ages! More information can be found online at Wesley Wells Farms.
October
St. Benedict Blues Festival 2025 – Friday, October 24th to Sunday, October 26th
Blues and BBQ! St. Benedict the Moor Church will host their annual Blues Fest for three days in October in historic Lincolnville, featuring musicians from Northeast Florida and beyond. All you need to bring is a lawn chair and your appetite! Home cooked meals for purchase include seafood gumbo, chicken and andouille sausage gumbo, barbecue ribs, fried fish sandwiches on Friday and barbecue rib dinner on Saturday. Sunday brunch includes quiches, pancakes and more delicious breakfast treats — and there’s always a dessert table, and beer, wine and soft drinks. More information can be found on their Facebook.
Sykes Family Farms Crop Maze – Begins October 4th 
Explore the award-winning crop maze and fall activities at Sykes Family Farms, Fridays, Saturdays and Sundays from October 4th to November 2nd. Every year the maze is truly unique, spread out over nine acres and full of twists and turns. There are also an amazing amount of activities for the whole family, including the kiddie cow train, hay rides, bubble barn and duck races — with yummy festival foods like corn dogs, chips, dill pickles, kettle korn and boiled peanuts. Get all the information, and tickets, online at Sykes Family Farms.
November
Nights of Lights – Begins November 15th 
Most definitely the most magical time in St. Augustine, Nights of Lights kicks off the holiday season. Listed among the Top Ten Holiday Light Displays in the World by National Geographic, the entire downtown is aglow with millions of tiny, sparkling holiday lights. It’s free to see, so wander around the beautiful old streets, sip cocoa and take in the enchantment. We here at Florida Water Tours even have a special tour for the occasion! Cruise on one of our world-class charters, with complimentary 3D glasses to enhance your experience and holiday music to get you in the spirit.
And don’t forget to get out on the water all fall long with Florida Water Tours! It’s truly the best way to experience St. Augustine, and especially in the fall. The Moonlit Mysteries Tour takes you out in the dark of night, jet setting just after sunset. Our expert guides share the haunted, spooky tales of the oldest city. Perfect for teens and adults, and tickets include one beverage from the bar (for guests 21+).
With more unique tours and private charters available, we welcome you to celebrate the seven seas with us at Florida Water Tours. We’re located at Windward Camachee Cove Yacht Harbor, 107 Yacht Club Dr., St. Augustine, FL 32084. We offer free parking and restrooms are on board. Our vessels are just a short walk from our boutique, located at Dock A-23, A-24 and A-25. Email us at [email protected] to book or inquire about your next cruise.