October in Northeast Florida comes with a packed calendar. Here's what's happening across Duval, Clay, and St. Johns counties this month — every event linked to the organizer's own page so you can double-check times before you head out.
Quick answer: What's happening around Jacksonville in October 2026? The biggest weekend is Oct 16–18: Beaches Oktoberfest (Oct 16–17), the free NAS Jacksonville Air Show (Oct 17–18), and the Orange Park Fall Festival (Oct 17–18). Add in a St. Augustine 5K, a spooky storytelling night, pumpkin patches, markets, and trunk-or-treats all month long.
When is the Pink Up the Pace 5K in 2026?
Saturday, October 3, 2026, 8:00 a.m. start at 25 W Castillo Dr, St. Augustine. The 5K walk/run raises money for breast cancer early-detection services for uninsured and underinsured St. Johns County residents. Registration is required. Register on RunSignup
What is Dark and Stormy Night in St. Augustine?
The 13th annual Dark and Stormy Night is Wednesday, October 14, 2026, 7:30–9:30 p.m. (doors at 7:00) at the Limelight Theatre, 11 Old Mission Ave. Tale Tellers of St. Augustine take the stage for an evening of live spooky storytelling. Tickets are sold in advance online. Event details
When is Beaches Oktoberfest 2026?
Friday–Saturday, October 16–17, 2026 in Jacksonville Beach — a two-day Oktoberfest-style festival with beer and live music. Check the official site for times and tickets. Visit Jacksonville listing · Official site
When is the NAS Jacksonville Air Show and is it free?
Saturday–Sunday, October 17–18, 2026 at Naval Air Station Jacksonville. Admission is free and no tickets are required. Gates open at 9:00 a.m., the show starts at 11:00 a.m., and the Blue Angels close the show around 3:00 p.m. (The Friday practice show is not open to the public.) Official air show info
When is the Orange Park Fall Festival 2026?
Saturday–Sunday, October 17–18, 2026 at Town Hall Park, 2042 Park Ave, Orange Park. The Town of Orange Park's annual two-day festival brings artists, vendors, food, and entertainment to the park. Festival website
When is the Green Cove Springs Police Trunk-or-Treat?
Friday, October 23, 2026. The Green Cove Springs Police Department hosts a community trunk-or-treat with decorated cars handing out candy. Check the City's page for time and location. [CHRIS: delete this note after verifying — date is per CBV; City site not checked yet.] City of Green Cove Springs
Other Honorable Mention October Events
Jacksonville & the Beaches (Duval)
Golden Harvest Market & Plant Sale — Sat Oct 3, 10 a.m.–4 p.m., Cummer Museum (829 Riverside Ave). Fall plants and local makers on the front lawn; free admission. Details
Riverside Arts Market — Every Saturday, 10 a.m.–3 p.m., under the Fuller Warren Bridge (715 Riverside Ave). Farmers, artists, and makers, rain or shine. Details
WasabiCon 2026 — Oct 9–11, Prime F. Osborn III Convention Center. Jacksonville's pop culture convention: anime, cosplay, and gaming. Ticketed. Details
Jax Beach Arts Market — Sat Oct 24, 10 a.m.–4 p.m., Seawalk Pavilion. Local artists on the oceanfront; free admission. Details
Treats at the Plaza! — Sat Oct 31, 1–5 p.m., Riverfront Plaza downtown. A JaxParks trunk-or-treat; costumes encouraged. Details
Clay County
Amazing Grace Farms Pumpkin Festival — Oct 2, 3 & 9 (more dates on the farm's calendar), Amazing Grace Family Farms, Green Cove Springs. Crop maze, pumpkin patch, and farm animals. Ticketed. Details
Dig N Dirt — Oct 3–4, 10 a.m.–3 p.m., Clay County Fairgrounds. Kids climb on real construction equipment; food trucks on site. Details
Fleming Island Saturday Market — Sat Oct 3, 9:30 a.m.–2 p.m., Village Square Shopping Center. Monthly local market, first Saturday of each month. Details
National Night Out — Tue Oct 6, 5–8 p.m., Clay County Fairgrounds. The Clay County Sheriff's Office hosts games, music, food trucks, and a chance to meet local officers. Details
St. Johns County
Sykes Family Farms Fall Crop Maze — Fridays–Sundays, Oct 3–Nov 1, Elkton. Crop maze, hayrides, and bounce pads. Ticketed. Details
Cracker Day Festival — Sat Oct 10, 9 a.m.–6 p.m., St. Johns County Fairgrounds. The Cattlemen's Association's 67th annual celebration of Florida Cracker horses and cattle — pony rides, petting zoo, and more. Per-car admission, cash only. Details
Halloween Trick-or-Treat Festival — Sat Oct 24, 1–4 p.m., Ximenez-Fatio House Museum, St. Augustine. Trick-or-treating, games, and prizes; free. Details
Ancient City Kids Day — Sat Oct 24, 11 a.m.–3 p.m., Francis Field, St. Augustine. 50+ booths with games, crafts, and live entertainment; free admission. Details
Frequently Asked Questions
Is the NAS Jax Air Show free? Yes. The official site says admission is free and no tickets are required for the Oct 17–18 show.
Where can kids trick-or-treat around Jacksonville in October 2026? Green Cove Springs Police Trunk-or-Treat (Oct 23), Ximenez-Fatio House in St. Augustine (Oct 24), and Treats at the Plaza downtown (Oct 31).
What are free things to do around Jacksonville this October? The NAS Jax Air Show, Golden Harvest Market at the Cummer Museum (free admission), Jax Beach Arts Market (free admission), Ancient City Kids Day (free admission), and the Ximenez-Fatio House trick-or-treat.
Love Where You Live
Whether you're exploring a new part of town or already call Northeast Florida home, we're here when you have real estate questions. Search homes across Duval, Clay, and St. Johns at courtneyteam.com, or reach out to Chris (904-479-6922) or Kristi (904-479-8935). #ForeverFamilyForeverHome
Chris & Kristi Courtney, REALTORS® · The Courtney Team · Coldwell Banker Vanguard Realty. Event details come from each organizer's public page as of October 1, 2026 and can change — please confirm with the organizer before you go. The Courtney Team is not affiliated with these events or their organizers.
