September 2026 Events
Sing Out Loud
September 2026
Multiple Venues
St. Augustine, FL
The Sing Out Loud Festival is back for the month of September!
This annual celebration of music features FREE concerts by local and regional artists who define the festival, with more than 100 artists performing at 17 venues across St. Johns County. The free Local Artist Showcases are presented by PNC Bank.
First Friday Artwalk
September 4, 2026 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.
Aviles Street Festival
September 5, 2026
Aviles Street
St. Augustine, FL 32084
On September 5th, head downtown for the Aviles Street Festival!
Celebrate Spanish Heritage Month on the oldest street in the nation, right in the heart of St. Augustine!
Step back in time and experience the sights, sounds, and spirit of historic Aviles Street as we celebrate the rich history and Spanish heritage that helped shape America’s oldest city. Enjoy live music, flamenco dancers, sword dueling, art, history, boutique shopping, and delicious food in the vibrant atmosphere of this one-of-a-kind historic district.
This event is free & family-friendly. NO tickets required!
Wild September Nights
September 11, 2026 at 6 to 9 p.m.
St. Augustine Alligator Farm and Zoological Park
999 Anastasia Boulevard, St. Augustine, FL 32080
St. Augustine Alligator Farm and Zoological Park’s Wild September Nights Night Market returns on September 11th.
Explore portions of the St. Augustine Alligator Farm while shopping from a curated selection of local vendors and learning from local conservation groups, all while supporting conservation!
End of Summer Beach Bash
September 12, 2026 at 9 a.m. to 1 p.m.
St. Augustine Beach Pier Park
350 A1A Beach Boulevard, St. Augustine Beach, FL 32080
Say goodbye to summer with sun, sand, and a whole lot of fun at City of St. Augustine Beach’s End of Summer Beach Bash! Bring your friends and family out to the St. Augustine Beach Pier Park for a lively morning packed with entertainment, friendly competitions, and community spirit.
461st Anniversary Founders' Day Celebration
September 12, 2026 at 10 a.m. to 4 p.m.
National Shrine of Our Lady of La Leche at Mission Nombre de Dios
101 San Marco Avenue, St. Augustine, FL 32084
On September 12th, join the annual commemoration of the founding of the city of St. Augustine 461 years ago as Spanish Admiral Pedro Menendez and his fleet made landfall and were greeted by the indigenous Timucuan tribes.
Old City Home and Garden Expo
September 12, 2026 at 10 a.m. to 5 p.m.
Francis Field
24 West Castillo Drive, St. Augustine, FL 32084
Join ArtiSUN Markets on Saturday, September 12th, from 10 a.m. to 5 p.m. at Francis Field in beautiful St. Augustine for a fun-filled, family-friendly Home & Garden Expo!
This FREE event will include local vendors showcasing their goods & services aimed at bringing beauty & unique character to your home, indoors & out.
St. Augustine Book Festival
September 19, 2026 at 10 a.m. to 3 p.m.
Ximenez-Fatio House Museum
20 Aviles Street, St. Augustine, FL, 32084
Happening September 19th is the Fourth Annual St. Augustine Book Festival!
Spend the day celebrating books, stories, and literary discovery in the beautiful courtyard of the Ximenez-Fatio House Museum, located in the heart of downtown St. Augustine!
St. Augustine Songwriters Festival
September 24 through 27, 2026
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.
Concerts for a Cause
September 26, 2026 at 5:30 p.m.
Tringali Barn
7310 U.S. 1St. Augustine, FL 32086
On September 26th, head to Tringali Barn to see platinum-award-winning singer/songwriter Jackson Dean play Concerts for a Cause.
Concerts For A Cause 2026 will benefit the St. Augustine Youth Services’ (SAYS) Independent Living Village, a project aimed at providing young men aging out of foster care a home while they take their next steps, still having critical support nearby. The Independent Living Village will consist of eight two-bedroom, two-bathroom townhomes.
Pumpkin Festival and Handmade Market
September 26, 2026 at 9 a.m. to 4 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 giant pumpkin patch in St Augustine where you can pick your own pumpkin straight off the vine.
Mark your calendars for Saturday, September 26th for Wesley Wells Farms’ 2026 Pumpkin Festival + Handmade Market!
Wesley Wells Farms is thrilled to kick off the fall season with their 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!
Art and Bark in the Park
September 27, 2026 at 11 a.m. to 4 p.m.
Lakeside Park
2340 A1A South, St. Augustine,FL 32080
Join City of St. Augustine Beach for a fun-filled day at Lakeside Park.
Bring the whole family out to enjoy local vendors, art, music, food, and plenty of furry friends. Come meet adoptable pets and support our community animal organizations while enjoying a beautiful day at the park.