St. Augustine in October: The Guide to Meaningful Fall Experiences

St. Augustine in October is very exciting! Local businesses really shine, sharing thoughtfully created experiences that are different and exceptional. We can hardly wait for October in St. Augustine and have filled our calendar with some of these unique, meaningful and haunted events. We wish we could do it all!

St. Augustine In October: Unique and Curated Evenings

Our favorite night time experiences are, atmospheric, and built for connection — the kind of evening our own guests come to Magic Hideaway for.

The Magic Hideaway – a 22 seat intimate theatre sharing magic and mind reading in your hands. Every Saturday night.
The Gilded Table: A Candlelit Orchestra Dinner Series — Oct 23. Stunning live orchestral music paired with a multi-course dinner. 
The Velvet Underground Show. An elegant immersive Speakeasy Experience— Fri, Oct 2. 
Headless Bangers Costume Ball . A Halloween ball with live music, a costume contest, and scary animatronics. Oct 24
The Alchemist’s Assembly – An immersive Halloween celebration featuring artists, mystical experiences, enchanting entertainment under the stars. October 31st.
A Starlight Stomp at Wesley Wells Farms BBQ, Bonfires & Boot Scootin’ Under the Stars— Oct 2
Annual Sizzlin’ Soirée . A social fundraising event to empower local youth— Oct 1. 
Beetlejuice Pub Crawl A creepy crawl in the city with The Tasting Tours all throughout October
First Friday Art Walk Concert A free concert series at the beautiful Cathedral Basilica — Oct 2. 
 Ancient City Poets: Sunday Series. An open mic welcoming platform for poets— Oct 25. 
St. Augustine Film Society presents “The Class”, an award winning documentary – October 5
CrimeWave: A Goth, Post-Punk & Darkwave Party Haunting sounds of goth, darkwave, new wave, post-punk, and industrial music. at Cafe Eleven —Oct 23. 
Emo Social Dance Party at Cafe Eleven. An explosive night of emo, alternative, and rock — Oct 3.
Spinster Abbott’s annual halloween party The town’s local famous costume contest
St. Augustine Songwriters Competition — A call for songwriters to share and perform with multiple dates in October

St. Augustine Halloween 2026: Haunted Historic Nights

Every October, the city of St. Augustine gets a little more haunted. St. Augustine Halloween is built on centuries of real ghostly history. We love walking through downtown to feel its rich spooky history.

Paranormal Investigation at the Castillo de San Marcos — Thu–Sat, starting Oct 1. An intimately guided ghost investigation inside a 17th-century fort. 
Mortality and Mourning: Women in Black — multiple dates in October. A quietly powerful look at Victorian mourning traditions. 
The 13th Annual Dark and Stormy Night — Oct 14. A local literary tradition built around gothic storytelling. 
EstuScary Haunted Trail at GTM Reserve. A spine-chilling nature adventure — Oct 29–31.
A Night Among Ghosts: Overnight Paranormal Investigation An all night haunted experience— Oct 17-18.

St. Augustine Fall Community & Family Traditions

These are our very top neighborhood-feel events that are different and perfect for experiencing St. Augustine in October with your whole family young and old.

Taste of Latino Festival (Empanada Smackdown & Líderes Awards) — Sun, Oct 4. 
Dracula by St. Augustine Ballet — Sun, Oct 11, 3–5pm. A dark, thrilling dance performance.
Mad Monster Halloween Market — Spooky vendors, meet and greets, music and food. Oct 10.
Annual St. George Street Trick or Treating with Ancient City Tours — a 21-year local tradition
Croctoberfest Brew at the Zoo, at the Alligator Farm -October 3
Hastings Trunk or Treat & Movie in the Park — Spooky family fun Oct 24. 
Tricks and Treats at the Beach PD . Rescue vehicles, popcorn, games, family fun— Fri, Oct 16, 5:30pm. 
Annual Halloween Dress-up Party at Ready Set Play — Meet your Favorite Crime Fighting Pooch Fri, Oct 16, 4:30pm. 
Trick-or-Treating and Harvest Festival at the Ximenez-Fatio House Museum — safe trick-or-treating, games, prizes, and festive fun for all ages. Sat, Oct 24, 1pm. 
Studs & Suds at Bog Brewing Company — Mon, Oct 26, 4pm. A fundraiser supporting affordable housing and veterans.
Creatures of the Night at the Alligator farm— Oct 23 & 24. 
St. Augustine Fall Triathlon— Oct 11. 
Drum Runner Series Barrel Racing for horse lovers— Oct 3.
Family Seining — Pull a seine net through Guana Lake, collecting species of fish, crabs, and other habitats. Oct 10.

October in St. Augustine is one of our favorite times of year and is full of nights worth remembering.

If you’re looking for one more evening built around connection, laughter and meaningful memories, the Magic Hideaway is an intimate magic show in St. Augustine unlike any other — a one-hour, close-up performance for just 22 guests inside Casa Monica Resort & Spa, with magician Bill Abbott working sleight of hand inches from your seat. The room is small and shows go early, so reserve your seats now at magichideaway.com/buy-tickets.

We’re Bill and Rebecca Abbott, and we’re excited to share our personal favorite St. Augustine discoveries – from unforgettable dining and entertainment to the hidden gems that make this city magical.

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