Jump into 2026 Fall Festivals!
Sing Out Loud Festival
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.
Aviles Street Festival
September 5, 2026
Aviles Street, St. Augustine, FL 32084
On September 5th, head downtown for the Aviles Street Festival to celebrate Spanish Heritage Month on the oldest street in the nation.
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!
Old City Home and Garden Expo
September 12, 2026
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 downtown 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
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 during this free community event featuring a curated selection of Florida authors, along with opportunities to connect with readers, discover new books, and enjoy a day dedicated to the literary arts.
St. Augustine Songwriters Festival
September 25-27, 2026
Multiple Venues
St. Augustine, FL
In partnership with Sing Out Loud, St. Augustine Songwriters Festival offers a unique perspective on the music scene by bringing hit songwriters to historic downtown St. Augustine. In addition to performing their chart-topping hits, songwriters will share testimonies, and offer a rare behind-the-scenes glimpse into their writing processes.
Participating venues include Colonial Oak Music Park, Prohibition Kitchen, St. Augustine Distillery, and Tradewinds Lounge.
For an up-to-date schedule and to learn more about each songwriter and their work, visit the St. Augustine Songwriters Festival online.
Pumpkin Festival and Handmade Market
September 26, 2026
Wesley Wells Farms
3455 Joe Ashton Road, St. Augustine, FL, 32092
Wesley Wells Farms’ annual Pumpkin Festival and Handmade Market is happening Saturday, September 26th from 9 to 4 pm.
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!
CROCtoberfest
October 3, 2026 at 6 to 9 p.m.
St. Augustine Alligator Farm
999 Anastasia Boulevard, St. Augustine, FL, 32080
This conservation event is held on the first weekend of October each year. The St. Augustine Alligator Farm Zoological Park partners with breweries and vendors throughout Florida to offer sample beers, food, and live music as you stroll through the zoo and learn about conservation work happening right here in St Johns County.
St. Johns County Cracker Day
October 10, 2026 at 9 a.m. to 4 p.m.
St. Johns County Fairgrounds
5840 SR 207, Elkton, FL 32033
SJC Cracker Day returns to the St. Johns County Fairgrounds on October 10th!
The St. Johns County Cattlemen’s Association’s annual event will again feature a farmers market from 9 a.m. to 4 p.m., kids’ activities, entertainment and of course horse games!
Admission is only $5 per vehicle and onsite camping is available. Visit their Facebook page for details.
St. Augustine Greek Festival
October 10 and 11, 2026
Holy Trinity Greek Orthodox Church of St. Augustine
2940 County Road 214, St. Augustine, FL, 32084
Be Greek for the Weekend!
Immerse yourself in authentic Greek culture and heritage during the St. Augustine Greek Festival, happening October 10–11, 2026 at Holy Trinity Greek Orthodox Church of St. Augustine.
The event is FREE and open to the public. Festival hours are Saturday from 11 a.m. to 8 p.m. and Sunday from 11 a.m. to 5 p.m. Take out or eat in and enjoy the festivities... or better yet, eat in AND take out to enjoy later.
Vilano Music Fest
October 17, 2026
Hyatt Place - Vilano Beach/St. Augustine
117 Vilano Road, St. Augustine, Florida, 32084
Catch the Vibe at Vilano Beach’s biggest party of the year, happening at Hyatt Place Hotel.
Vilano Music Fest brings together an incredible lineup of rock legends and local favorites for a beachside music festival that spans the decades.
St. Benedict Blues Festival
October 23 - 25, 2026
Saint Benedict of the Moor Catholic Church
86 Martin Luther King Avenue, St. Augustine, FL 32084
The Saint Benedict the Moor Blues Festival will be held on October 20th through 22nd to benefit the Saint Benedict the Moor Catholic Mission Rectory Fund.
The annual festival features some of the best blues performers, amazing home-cooked food, and tons of fun.
Click the button above for details and the full line-up of this year’s performances.
Ancient City Kids’ Day
October 24, 2026
Francis Field
25 West Castillo Drive, St. Augustine, FL 32084
Coordinated by EPIC Behavioral Healthcare and brought to the community by a committee of children organizations, Ancient City Kids Day is a day of fun-filled activities for children and families.
The event is free for the public and will include more than 40 youth service organizations each of whom will offer games, activities, crafts, give-aways, bounce houses or fun contests for kids. They will also be offering resource information for parents regarding programs and services in the community.
Boots, Bands and Big Dreams: A Benefit for HorsePlay Therapy Center
October 24, 2026
Kelly Farms
5895 County Road 214, St Augustine, FL 32092
Boots, Bands, and Big Dreams, a benefit for HorsePlay Therapy Center, will be held at Kelly Farms (the center’s future neighhhbbors!!!) Happening October 24th at 5:30 p.m., this fundraising event features good tunes, tasty treats, and a hay ride out to HorsePlay Therapy’s future home to see their vision! Get tickets at horseplaytherapy.org.
Great Chowder Debate
November 1, 2026
Conch House Resort Marina
57 Comares Avenue, St. Augustine, FL 32080
The Great Chowder Debate is back on November 1, 2026 at the Conch House Resort Marina. One of St. Johns County’s favorite events, you do not want to miss your opportunity to taste all the incredible chowders and soups while supporting a great cause. All proceeds from this year’s event will go to Big Brothers Big Sisters of St. Johns County.
Hastings Fall Harvest Festival
November 6 and 7, 2026
Hastings Main Street
North Main Street, Hastings, FL, 32145
Celebrate Hastings’ agricultural roots at the Hastings Main Street Fall Harvest Festival, a two-day experience centered on local farms and rural heritage.
Begin the weekend on Friday, November 6th at 11 a.m. with a Farm Tour. Continue the festivities on Saturday, November 7th with free, family-friendly activities along North Main Street, including live performances, a Kids Zone, and a curated vendor area.
St. ARTistine Art & Food Festival
November 7, 2026
Francis Field
24 West Castillo Drive, St. Augustine, FL, 32084
Join ArtiSUN Markets for the 2nd Annual St. ARTistine Art & Food Festival on Francis Field in St. Augustine on Saturday, November 7th from 10 a.m. to 5 p.m.
A brand new year of exciting local artists, crafters, bakers, authors, performers, food trucks, and family festivities with FREE admission to the public!
Florida Key Lime Pie Festival
November 14, 2026
24 West Castillo Drive, St. Augustine, FL, 32084
Hosted by The Florida Key Lime Pie Company, the original Florida Key Lime Pie Festival is coming to St. Augustine on Saturday, November 14, 2026.
Festival-goers can expect a full day of family-friendly fun, food, and Florida flavor.