September 2025 Events
Aviles Street Festival
September 5 and 6, 2025
Aviles Street
St. Augustine, FL 32084
Head to the Second Annual Aviles Street Festival as we celebrate Spanish Heritage Month on the oldest street in the oldest city in America — Aviles Street! The festival takes place on Friday, September 5th from 4 PM to 9 PM (during First Friday Art Walk) and Saturday, September 6th from 12 PM to 9 PM.
The merchants, museums, galleries, and restaurants along Aviles Street invite you to enjoy two days of fun, food, music, art, and history. Highlights include invited plein air artists, live music, flamenco dancers, sword dueling demonstrations, boutique shopping, and much more.
First Friday Artwalk
September 5, 2025 at 5 p.m. to 9 p.m.
Historic Downtown and Anastasia Island
St. Augustine, FL
The Art Galleries of Saint Augustine founded and sponsors the award-winning First Friday Art Walk event on the first Friday of every month. Galleries open their doors from 5 to 9 p.m., offering new art exhibits and lively receptions to the public.
End of Summer Beach Bash
September 6, 2025 at 12 p.m. to 4 p.m.
St. Augustine Beach Pier
360 A1A Beach Boulevard, St. Augustine Beach, FL, 32080
Celebrate the end of summer with the City of St. Augustine Beach at our End of Summer Beach Bash – a FREE event full of family fun and island vibes!
Watermelon Eating Contest
Music
Hula Hoop Contest
Ugly Hawaiian Shirt Contest
Local Vendors
And more beachside fun!
Bring your friends, family, and your best (or worst!) Hawaiian shirt and join us at the pier for an afternoon of laughter, games, and community celebration!
Coastal Country Indoor Market
September 13, 2025 at 10 a.m. to 2 p.m.
Coconut Barrel
2121 U.S. 1, St. Augustine, FL, 32086
Coconut Barrel is saying goodbye to summer country style — indoors and in the A/C! On Saturday, September 13th, join them for the Coastal Country Indoor Market, a fun-filled, family-friendly event featuring:
40+ Local Vendors
Live Country Music (Joshua "Tennessee" Worthy)
Line Dancing Demo by St. Augustine Line Dancers with Renie
Prizes & Drawings
FREE Sweet Tea
Tasty Food Samples
Artist Demonstrations
Plus, kids get a FREE cowboy hat & stick horse!
Dress up in your best country gear for a chance to win gift cards and gift baskets in our exclusive giveaway!
Bring the whole family for shopping, dancing, sipping, and celebrating the best of local artisans before summer rides off into the sunset! Drinks, drawings and kid gifts are all while supplies last.
St. Augustine Book Festival
September 20, 2025 at 10 a.m. to 4 p.m.
Ximenez-Fatio House Museum
20 Aviles Street, St. Augustine, FL, 32084
Happening September 20, 2025 is the Third Annual St. Augustine Book Festival, hosted by the Ximenez-Fatio House Museum on historic Aviles Street—the oldest street in the United States.
Discover a wide variety of authors and genres, including children’s books, fiction, Florida history, and more. Enjoy author meet-and-greets, explore exciting new works, and take a ticketed tour of our 227+ year-old historic house. This event is free to all, and donations are appreciated to support the preservation of our museum.
Give Kids the World Day
September 20, 2025 at 11 a.m. to 4 p.m.
Guy Harvey Resort
860 A1A Beach Boulevard, St. Augustine Beach, FL, 32080
Head to Guy Harvey Oceanfront Resort for an incredible day of family fun for an even more incredible cause during the 27th Annual Give the Kids the World Day.
Hosted by Guy Harvey Resort in St. Augustine Beach, this event features music, a youth art show, an abundance of kids’ activities, local vendors, pool time, silent and live auctions, raffle prizes and awesome food and drinks.
ALL proceeds from this annual fundraising event benefit Give Kids the World (GKTW) Village, a nonprofit providing FREE vacations to critically ill children and their families.
The Vilano Beach Artisan Market
September 20, 2025 at 4 p.m. to 8 p.m.
Vilano Beach Main Street
190 Vilano Road, St. Augustine, FL, 32084
The third Saturday of every month, head to the Vilano Beach Artisan Market. This cool market lines the beautiful sidewalks of Vilano Road and hosts dozens of local vendors and artists.
Whether you’re shopping for unique handmade items, enjoying delicious food, or soaking up the community vibes, there’s something for everyone at this vibrant open-air market.
Come catch the Vilano Vibe and discover some of our areas’ most unique treasures!
HorsePlay 10 Year Anniversary Gala
September 20, 2025 at 6 p.m.
Tringali Barn
7310 U.S. Route 1, St. Augustine, FL, 32086
Announcing their BIGGEST celebration yet! HorsePlay Therapy Center will be celebrating 10 years of serving children and veterans! Tickets are LIVE on our website! This celebration will include a delicious dinner from St Augustine eateries, live music and more. It’ll be the party of the decade!
All proceeds will help HorsePlay Therapy Center begin development on our forever home!
Sing Out Loud: Live Wildly Showcase
September 20 and 21, 2025
Francis Field
25 West Castillo Drive, St. Augustine, FL, 32084
Hozier, Beabadoobee, Vance Joy and The Teskey Brothers will headline the 2025 Sing Out Loud Festival on September 20th and 21st.
The Live Wildly Showcase, a two-day concert event at Francis Field, will feature additional performances by Rilo Kiley, Father John Misty, Maren Morris, Gigi Perez, David Kushner and more!
She is Fierce Summit
September 25, 2025 at 9 a.m. to 3 p.m.
Fountain of Youth
11 Magnolia Avenue, St. Augustine, FL, 32084
A luxury event filled with inspiration, practical professional development, and the network you need!
Head to She is Fierce, Business on the Bay, for a day filled with inspiration, practical professional and entrepreneurial business development, and the network you need... all at the stunning Fountain of Youth in St. Augustine, Florida... Presented by Bozard Lincoln!
Keynote speakers will share their inspiring stories of overcoming challenges and bringing their dreams to life.
Join with female leaders and women on the rise for a day of inspiration, business growth, strategic career planning, and personal development.
This luxe day includes breakfast, lunch, treats, wellness breakouts, and more!
St. Augustine Songwriters Festival
September 26 through 28, 2025
Multiple Venue
St. Augustine, FL
Get ready to immerse yourselves in a musical extravaganza at the St. Augustine Songwriters Festival. Picture yourself amid captivating performances, where top-notch hitmakers come together to unravel the untold stories and inspirations behind their sensational chart-toppers. From heartwarming anecdotes to unexpected twists, this festival is a treasure trove of secrets that will leave you enchanted and craving for more.
Pumpkin Festival and Handmade Market
September 27, 2025 at 9 a.m. to 5 p.m.
Wesley Wells Farms
2680 Ada Arnold Road, St. Augustine, FL, 32092
Ready for some fun fall action on the farm? Visit the only pumpkin patch in St Augustine, FL where you can pick your own pumpkin straight off the vine.
Mark your calendars for Saturday, September 27th for the 2025 Pumpkin Festival + Handmade market!
Wesley Wells Farms is thrilled to kick off the fall season with their very own you-pick pumpkins, you-pick veggies and flowers, crop maze, live entertainment, food trucks, photo ops, handmade craft vendors, farm animals, kid zone, and so much more!
Fall Fling Festival
September 28, 2025 at 12 p.m. to 4 p.m.
St. Augustine Rod and Gun Club
401 Gun Club Road, St. Augustine, FL, 32095
The Fall Fling Family Festival will take place on Sunday, September 28th to raise funds for the new Clean Start laundry facilities at Goff Family Shelter.
The festival will be a lively, family-friendly community event featuring live music, kids’ activities, local vendors and artisans, food trucks, hay rides, pumpkin painting and more!
The goal is to raise $10,000 for the new Clean Start laundry facilities at the Goff Family Shelter (currently under construction) to provide families a space to do laundry. This facility will shelter nine families with minor children, providing stability and a safe place to rebuild their lives.