October 2026 Events
First Friday Artwalk
October 2, 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.
Coconut Barrel Fall Craft Market
October 3, 2026 at 10 a.m. to 3 p.m.
Coconut Barrel
2121 U.S. 1, St. Augustine, FL, 32086
Mark your calendars for Saturday, October 3rd, from 10 a.m. to 3 p.m. for Coconut Barrel’s Fall Craft Market!
Shop more than 45 outdoor vendors featuring handmade treasures. Enjoy delicious bites from local food trucks and relax to live entertainment throughout the day. After exploring outside, head in to the complimentary cider bar.
Sip, shop, and discover the best of St. Augustine’s local art and artisans.
Sykes Family Farms Corn Maze
October 3 - November 1, 2026
Sykes Family Farms
Sykes Family Farms5995 Brough Road, Elkton, FL, 32033
The Crop Maze at Sykes Family Farms is back! The 2026 maze will be open October 3rd through November 1st.
Sykes Family Farms combines a 9-acre corn maze full of “cornfusing” twists and turns. Mix it all together and you have “Agritainment”! After you conquer the maze, guests can enjoy the rest of the day visiting all of the farm’s attractions.
CROCtoberfest
October 3, 2026 at 6 p.m. to 9 p.m.
St. Augustine Alligator Farm
999 Anastasia Boulevard, St. Augustine, FL, 32080
On the first weekend of October each year, the Alligator Farm celebrates crocodilians through their Brew-at-the-Zoo, Croctoberfest! This conservation event features breweries and vendors from throughout Florida. You can sample beers from your neighborhood breweries as you learn about conservation work happening right here in St Johns County.
Local restaurants will also be onsite dishing out some of their favorites. The full list of participating breweries, restaurants, conservation organizations, and more is posted at the beginning of each September.
This is a strictly 21 and older event. No children, including infants or toddlers, are permitted.
Taste of Latino Festival
October 4, 2026 at 12 p.m. to 6 p.m.
Franice Field
24 West Castillo Drive, St. Augustine, FL, 32084
Celebrate Hispanic Heritage Month during the Taste of Latino Festival.
This free community event, happening Sunday, October 4th, features an empanada and Cuban sandwich smackdown, plus Latino Lideres. (VIP tickets available on Eventbrite.)
Enjoy live music and dance performances (and classes!) as you taste your way through the area’s best Latin dishes.
St. Johns County Cracker Day
October 10, 2026 at 9 a.m. to 4 p.m.
St. Johns County Fairgrounds
5840 Florida 207, Elkton, FL, 32033
Head to the 67th Annual Cracker Day and Market on Saturday, October 10th!
Watch, ride and learn about the Cracker Cattle and cowboy history. The event features lots of food options, activities, craft vendors, pony rides, cowboys, snacks and plenty of horses and horse races for your enjoyment. Fun for all ages!
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
Escape to Greece during the St. Augustine Greek Festival at Holy Trinity Greek Orthodox Church!
Happening October 10th and 11th, the annual event features authentic Greek food, pastry, music, dancing and more!
Enjoy a meal and spend the day celebrating Greek culture and heritage! Opa!
Pie in the Sky Harvest Hoedown
October 15, 2026 at 5 p.m.
Tringali Barn
3710 US 1, St. Augustine, FL 32086
Come celebrate 10 years of Pie in the Sky’s Senior Produce Program during the Harvest Hoedown - Boots, Bushels & Big Hearts, happening on Thursday, October 15, 2026 at Tringali Barn.
Each individual ticket includes: Live music and dancing, family-style fried chicken dinner by the famous Johnny Barnes, libations, live and silent auctions
So put on your boots, take a seat at the table, sip a scuppernong spritzer, and raise your paddle... there’s a place for you at the Harvest Hoedown. Help Pie in the Sky St. Johns continue the fight against hunger and isolation in our community.
Jimmy Jam Bourbon & BBQ
October 17, 2026 at 6 p.m. to 9 p.m.
Tringali Barn
7310 US Highway 1 South, St. Augustine, Florida, 32086
Mark your calendars for an unforgettable evening of incredible food, great company, and giving back to our community.
On Saturday, October 17th, join Jimmy Jam Community Outreach for the 3rd Annual Bourbon & BBQ, a charity event dedicated to raising funds that directly support local families right here in St. Johns County. Every ticket, every plate, and every moment of support helps us continue providing a hand up, not a handout, to those facing difficult times.
St. Benedict Blues Festival
October 23-25, 2026
St. Benedict 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 23rd through 25th to benefit the Saint Benedict the Moor Catholic Mission Rectory Fund.
This year marks the 14th year of the annual festival featuring some of the best blues performers, amazing home-cooked food, and tons of fun.
Creatures of the Night
October 23 and 24, 2026
St. Augustine Alligator Farm
999 Anastasia Boulevard, St. Augustine, Florida, 32080
Family-friendly trick-or-treating at the Zoo!
Head to the St. Augustine Alligator Farm for a spooktacular time with two nights of treats, costumes, and fun. Meet eerie bugs and beasts, explore the park, and fill your bag with treats. The ToucanTina Café will be open to purchase drinks and special treats.
10th Annual Jail Break 5K
October 24, 2026 at 8 a.m.
Old Town Trolley Tours
167 San Marco Avenue, St. Augustine, Florida, 32084
10 Years. Thousands of Runners. One Epic Escape.
Join INK! (Investing in Kids) and Old Town Trolley Tours of St. Augustine as they celebrate the 10th Annual Jail Break 5K on Saturday, October 24, 2026!
Lace up your running shoes and break free from the historic Old Jail Museum, a 130-year-old landmark, as you race through the beautiful streets of the Nation's Oldest City. Cross the scenic Vilano Bridge and make your getaway to the beach and the finish line beyond.
EPIC Ancient City Kids’ Day
October 24, 2026 at 11 a.m. to 3 p.m.
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.
There will be free t-shirts/goody bags for kids while they last and live entertainment all day.
Admission to this event is free!
Boots, Bands and Big Dreams
October 24, 2026 at 5:30 p.m. to 9 p.m.
Kelly Farms
5895 County Road 214, St. Augustine, Florida, 32092
Join HorsePlay Therapy Center at their annual fundraising event on October 24th: Boots, Bands, and Big Dreams!
The event will be held at Kelly Farm, HorsePlay Therapy’s future neighhhbbors. Come join them for some good tunes, tasty treats, and a hay ride out to their future home.
Sykes Family Farms Tractor Treat
October 31, 2026 at 10 a.m. to 10 p.m.
Sykes Family Farms
5995 Brough Road, Elkton, Florida, 32033
Tractor Treat is back at Sykes Family Farms on October 31st!
Grab the costumes, round up your little ghosts & goblins, and head to Sykes Family Farms for the Tractor Treat & Costume Contest! This is a fun, safe, family-friendly way to celebrate Halloween!