October Local Events in St. Augustine, FL

by Kevin Howard

If you’re looking to make October 2025 memorable in St. Augustine, here’s your curated guide to some of the standout local events. Whether you’re hoping to soak in live music, family-friendly fall fun, or spooky thrills, there’s something this month for everyone.

1. Pumpkin Patches & Fall Activites (Sep 27 – Nov 2)

The fall season is in full swing with pumpkin patches and related festivities throughout the region. These are great for families or for capturing seasonal photos. A few options:

Sykes Family Farms (Elkton): The crown jewel of local fall fun. Their 9-acre corn maze changes design every year and is perfect for both kids and adults looking for a challenge. Beyond the maze, you’ll find a pumpkin patch, hayrides, farm animals, bounce pads, and evening “flashlight maze” nights for a spookier experience. Open Fridays through Sundays, this is one of the most popular seasonal attractions in Northeast Florida.
Pumpkin Patch at First United Methodist Church: A local favorite where families can stroll through rows of pumpkins and gourds of every size. It’s a smaller setup compared to Sykes, but it’s convenient, welcoming, and makes for a relaxed outing with little ones. Proceeds often support community programs. This year's pumpkin patch is open for shopping each day from 11:00 a.m. to 7:00 p.m., beginning October 10, 2025, until the pumpkins are gone.
Other Local Spots: Several smaller patches pop up around the county, often hosted by local churches and schools. These are perfect for quick visits, supporting local programs, and grabbing a pumpkin without the big crowds.

2. Moonlit Mysteries: Haunted History Boat Tour

When: Thursdays through Saturdays from September 13 to November 14

Venture out on a nighttime water tour filled with ghost stories, starry skies, and historic lore. Click here for more info.

3. Croctoberfest at Alligator Farm

When: October 4, 2025 | 6:00 PM - 9:00 PM)

A grown-up night at the Alligator Farm — limited to ages 21+. Enjoy craft beers, food vendors, and a spooky, swampy atmosphere.

4. Pink Up the Pace 2025 — 5K Walk/Run

When: Saturday, October 4, 2025, 8:00 a.m. start

Where: Francis Field, 10 W. Castillo Dr., St. Augustine

St. Augustine’s largest 5K turns downtown into a sea of pink to kick off Breast Cancer Awareness Month. Proceeds stay local to fund breast-imaging and early-detection services for uninsured and underinsured residents. General registration is listed at $40 before September 30, with $25 options for survivors and ages 12 and under; prices may adjust as race day approaches. Packet pick-up is scheduled at Anastasia Baptist Church on Friday, October 3; check the official site for final hours.

5. National Night Out

When: October 7, 2025 | 5:00 PM – 8:00 PM

Where: St. Augustine Beach Pier

A community-building event with local law enforcement, first responders, entertainment, and neighborhood camaraderie.

6. St. Augustine Greek Festival

When: October 11–12, 2025

Where: Holy Trinity Greek Othodox Church

Immerse yourself in Greek culture with food, music, dances, and pastries at the annual Greek Festival - a local favorite!

7. “Dracula” Ballet by St. Augustine Ballet

When: October 12, 2025 | 4:00 PM

Where: Lewis Auditorium, Flagler College

A dark, enchanting performance steeped in gothic allure—part dance, part theater. Click here to tickets.

8. VIBE-Rations Music Festival

When: October 18, 2025 | 10:45 AM – 6:45 PM

Where: Vilano Beach

This one-day festival spotlights local bands and musical diversity.

9. Biketoberfest / Harley Events

When: October 16–19, 2025

Motorcycle rallies, parades, live music, and biker culture take over as St. Augustine taps into its “bike-friendly” season. One featured event: Ademec Harley Bike Night on October 16 (6:00 PM – 9:00 PM) at Harley Davidson of St. Augustine, with music, food, drinks, and bike show-offs.

10. Tedeschi Trucks Band “Live in 25”

When: October 24 & 25, 2025

Where: St. Augustine Amphitheatre

Catch this powerhouse blues/rock act at the St. Augustine Amphitheatre. There are a lot of incredible concerts at the Amp this month, including Jon Batiste, Ryan Bingham and the Texas Gentlemen, Cole Swindell and John Legend.

11. St. Johns County Master Gardener Fall Plant Sale

When: October 10–11, 2025 | 9:00 AM – 2:00 PM

Where: St. Johns County Agricultural Center

Pick up native plants, landscape specimens, and vegetable seedlings. A great opportunity to support local horticulture and beautify your garden. Click here for more info.

12. Headless Bangers Costume Ball 2025

When: Saturday, October 25, 2025 | 8:00 PM – Midnight

Where: Lewis Auditorium, Flagler College

Get your spook on at this annual costume gala benefitting local arts and historical preservation. Expect live DJs, themed décor, costume contests, specialty cocktails, and a festive, high-energy atmosphere. Tickets typically include a complimentary drink, and proceeds help support historic preservation and cultural programming in St. Johns County.

Fall in St. Augustine Truly is the Best Time of Year

October in St. Augustine brings the perfect blend of fall charm, culture, amazing weather and community energy. Whether you're visiting the nation's oldest city or a local seeking something new to enjoy, this lineup offers something for all tastes. Click here for a complete list of events taking place this month in St. Augustine.