#1 Halloween at The Wharf
One of Pass-a-Grille’s favorite Halloween traditions is back! This Saturday, October 31, The Wharf Waterfront Restaurant & Bar brings the spooky fun with a headless horseman, animatronic creatures and skeletons hanging from the rafters. Come in costume for the contest at 8pm, enjoy live music from Rob Tyre on the front porch and sip a Practical Magic Midnight Margarita between dances. Check out The Wharf’s October cover story to learn more about this loved local spot at https://www.paradisenewsfl.com/halloween-at-the-wharf/.
#2 Gulfport Witches Walk
Grab your witch’s hat and broomstick for a little Halloween magic, Gulfport-style! Their anual Witches Walk takes place this Saturday, October 31st, beginning at 5pm at The Village Courtyard (2902–2914 Beach Blvd. S.). Costumed witches will make their way through Gulfport before the festivities continue with a block party on Shore Blvd. Join the walk, show off your costume or cheer on the witches at this fun community Halloween tradition!
Learn more at https://www.facebook.com/share/p/1EJXYqcUKp/.
#3 Twisted Circus Party
Ready for a little Halloween after-dark fun? The Birchwood Canopy in downtown St. Pete goes full Twisted Circus this Saturday, October 31st 9pm. Expect twisted clowns, Halloween drinks, DJ Ali V spinning all night and plenty of surprises. Go all-in with a twisted circus costume, show off your Halloween best or simply come as you are. Admission is free, so gather your crew and head to the rooftop for a Halloween night out!
Learn more at https://www.facebook.com/events/962239000269825/.
#4 Haunted St. Pete Fest
Haunted Fest returns to the St. Pete Pier Friday & Saturday, October 30–31, from 5–10pm, bringing two nights of electronic music, international DJs and spooky-season energy right to the waterfront. The lineup includes Eli Brown, HUGEL, GORDO and more, plus a silent disco where you can switch between DJ channels. Costumes are encouraged, so dress up and dance under the stars! Tickets are $50+. Must be 18 or older.
Get tickets at https://www.breakawayfestival.com/festival/haunted-fest—st-pete-2026
#5 Fenway Fright Night
Looking for a Halloween night out with a little extra atmosphere? The historic Fenway Hotel in Dunedin transforms into Fenway Fright Night on Halloween, Saturday, October 31th, with live DJ entertainment, themed décor, haunted hallway tours, costume contests and late-night food stations. Dress to impress or terrify & enjoy a Halloween celebration with lots of spooky surprises! $69/person
Learn more at https://www.fenwayhotel.com/events/2026/fenway-fright-night-trick-package-standard-admission/,