Celebrating Halloween with Pub Crawl St. Augustine.

6 Wickedly Good Halloween Nights Out

Step into St. Augustine’s Halloween nightlife.

There’s something magical in the air when Halloween takes hold of St. Augustine. As the sun sets behind the bayfront and lanterns flicker along centuries-old streets, the nation’s oldest city sheds its historic calm for something a bit more eery. October here isn’t about candy buckets or trick-or-treat routes. Step into another world, embracing alter egos, and celebrating the season with bold costumes, classic horror films, and a drink (or two) in hand.

A dark image of the Headless Horseman, holding his pumkin head while riding his possessed horse

Headless Bangers Costume Ball

This Saturday evening event is the granddaddy of costume parties in St. Augustine. Held at the Legends Ballroom in World Golf Village, the ball features live tribute bands, costume contests with cash prizes, and theatrical touches like psychics and animatronics. It’s a full-night commitment — dress to impress.

Beetlejuice Pub Crawl

A fun, roaming costume-friendly crawl through local bars. Held Friday and Saturday evenings in October, participants follow the “dead guy” through spooky stops across town.

A drag queen performs in a pirate costume

Drag Queen-a-Palooza: Halloween Edition

Scheduled for October 17, this show blends camp, glam, and spooky in a costume-friendly drag performance. Don’t be surprised if outfits get theatrical and vibrant.

Improv Spooktacular

Between October 18 and November 1 (plus Halloween night), this show combines comedy and terror in short, audience-driven performances. Costumes are welcome and encouraged.

Jeepers Creepers at Waterworks

On Saturday, October 24, 2025, Waterworks hosts a horror film screening of Jeepers Creepers. While not a party in the traditional sense, the event’s cult status often draws attendees in costume and adds to the night’s Halloween energy.

A group of witches sitting around a table having tea

Witches Night In

This special event at 3rd Space Improv offers witches, warlocks, and the magically curious a chance to relax and recharge with a night of tarot, spell crafting, potion making, and other witchy pursuits. It’s less about high-volume partying and more about connection, creativity, and atmosphere.

If you’re looking to start or end your night with some Halloween cocktails, don’t miss the Black Lagoon pop-up at Forgotten Tonic or the Haunted Hideaway menu at Boat Drinks. These pop-up experiences offer the themed cocktails and Halloween flair you’re looking for. See our Spooky Sips article for full details.

Tips to Make the Night Unforgettable

Balance your evening: An ideal night might start with a cocktail pop-up, segue into a drag show or crawl, and end at a costume ball.
Tickets & reservations: Many ticketed events (like the Headless Bangers Ball) sell out — grab them early.
Go bold with your costume: These nights are meant for experimentation. From cult-classic glam to disco vampires, let your imagination run wild.
Stay local: Many venues are clustered around historic downtown, so plan walking or parking strategies in advance.

Have a Howling Good Time

From glittering masquerade balls to cinematic throwbacks and costume contests with real stakes, St. Augustine proves that Halloween nightlife is as much about creativity as it is about celebration. Whether you’re in it for the dance floor, the photo ops, or the thrill of becoming someone else for a night, one thing’s certain: there’s no better place to celebrate Halloween in costume than after dark in the Oldest City.