Halloween in Cayman: Little Boos & Big Scares

Nightmare on North Sound — Family Edition

October 23 – 31

Halloween’s younger adventurers get their turn at Dragon Bay Asylum during the earlier, gentler walkthrough. Atmospheric sets and costumed characters bring the spooky setting to life before the evening’s scares intensify.

Nightmare on North Sound — Adult Full-Scare Edition

October 23 – 31

The group chat’s bravest friend might have some explaining to do. Dark passages, unexpected encounters and theatrical scares turn this asylum-themed attraction into an evening for friends who enjoy being frightened together.

Save Our Youth Monster Dash 5K

October 24

Trainers meet Halloween costumes at this community charity run. A morning of movement and playful outfits gives runners, walkers and families a chance to celebrate the season while supporting local youth programmes.

Camana Boo’s Farmers & Artisans Market

October 25th

Local produce, handmade finds and seasonal treats give the Paseo a playful Halloween twist. This afternoon market offers a relaxed way to enjoy the festivities, browse Cayman’s makers and pick up something along the way.

Halloween Spookfest 2026

October 25–31

Costumes are part of the fun at this family celebration, with games, crafts, music and candy stations keeping little monsters busy. It’s a cheerful option for families who prefer their Halloween packed with play.

MyFirstGym Halloween Date Night & Ninja Party

October 30

Obstacle courses, games and Halloween costumes give children an energetic celebration of their own. MyFirstGym’s seasonal programme also offers parents an opportunity for an evening out around Camana Bay.

Trick or Treat at J. Michael

October 31

A little costume outing comes with a sweet reward at J. Michael. Children can collect treats in a festive shop setting, making this an easy daytime addition to Halloween plans.