This special area of the Portland Pirate Festival is devoted to kids, with a 24-foot climbing wall and five giant inflatable rides to suit a variety of ages, from toddler to adult. Besides rides, Scupper Monkey Island features a variety of kids entertainment and vendors, including puppets shows, strolling entertainers, a storytelling stage, and free face painting and temporary tattoos!

Kraken This giant slide is one of five thrilling kids' rides. Slide through the center of the doomed ship as it is cracked in half by the mystical Beast Kraken.
The Pirate and his Pet Puppet Show Dragon Theater Puppets presents the tale of a young boy finding courage and the truth from new friends.
Sea Creature Toddler Area All the fun of the big kid bouncers and slides only scaled down for little buccaneers. The Sea Creature Toddler Play Area features a small slide, and a dolphin, seahorse and whale for climbing.
The Pirate's Parrot Show is a Fun, Educational, and Interactive experience for all ages and cultures.
Golden Bough This kid-friendly trio of modern day minstrels will perform traditional sea-songs and songs about pirates and pirate lore from their newest CD .
Clowns Unlimited Presents 24’ Rock Climbing Wall
Scupper Monkey Island is inhabited by wandering performers such as Heather Pearl: Stilt-Walker, Clown, Physical Actor, and Circus Performer