Halloween in Anguilla looks a little different from the crisp autumn celebrations further north. Here, October 31 arrives with palm trees, warm tropical nights and a compact but lively event lineup that also marks the start of the busy winter tourism season.

This year, a lineup of Halloween events takes over the island on Friday, October 31, 2026 — from a family-friendly candy crawl to late-night costume parties on the beach.

Trunk or Treat: The Candy Crawl at the Ferryboat Inn

The Ferryboat Inn in Blowing Point hosts its annual Trunk or Treat Candy Crawl on October 31 at 5:00 PM. The evening includes free face painting, games and food and drink specials — a safe and fun way for families to trick-or-treat around the bay.

Tipsy Turtle's Annual Halloween Party with DJ Wifer

Tipsy Turtle keeps its annual Halloween tradition going on October 31, starting at 5:00 PM and running until late. DJ Wifer handles the music for a night of costumes, good vibes and seaside fun on the island's west end.

P.O.T 5 Halloween Party at the Dune Preserve

For the late-night crowd, P.O.T 5 brings a full performance lineup to the Dune Preserve on October 31, with doors opening at 10:00 PM. Performances come from DJ Tights, Frat Boys, Preshuh Pac, Mad Minoz and XL. Admission is $20 with a costume and $30 without, rising to $40 after 1:00 AM. Entry shots are on the house while supplies last.

Plan Your Halloween Night

Beyond the parties, Halloween weekend is a good excuse for families, friends and visitors to enjoy the island as the tourism season gets underway. And it's only the start of the events and experiences ahead this season.