Keiki Halloween at The Shops at Wailea draws crowd of 350 for costume contest, trick-or-treating, family fun

The Shops at Wailea welcomed over 350 guests to its annual Keiki Halloween celebration on Saturday, Oct. 24, bringing ʻohana together for an afternoon of costumes, candy and festive fun. Sponsored by Hilton Grand Vacations, the complimentary event featured trick-or-treating at more than 40 participating stores, balloon animals, costume contest, a magic show by Brenton Keith & His Bag O’ Tricks and a sugar skull-themed photo wall.

2026 Costume Contest First-Place Winners:

• Grand Prize & ʻOhana (Family): Car Wash
• Keiki Ages 0–2: Lilo from Lilo & Stitch
• Keiki Ages 3–5: Rapunzel
• Keiki Ages 6–10: Poke Bowl
• Pets: Prison Dog

First-, second- and third-place winners in each category received deluxe gift baskets featuring toys, snacks and gift cards. The winning family also received the grand prize of two round-trip flight vouchers valid on any Alaska Airlines or Hawaiian Airlines-operated flight between Hawaiʻi and North America.