Maui Arts & Entertainment

The Shops at Wailea celebrates Keiki Halloween with family-friendly festivities

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The complimentary event returns Saturday, Oct. 24, 2026 with center-wide trick-or-treating, a costume contest and more. Sponsored by Hilton Grand Vacations.

Costumes, candy and Halloween magic return to The Shops at Wailea with Keiki Halloween on Saturday, Oct. 24, from 3-7 p.m. Sponsored by Hilton Grand Vacations, the complimentary event welcomes ghouls and goblins of all ages for an afternoon of family-friendly fun including center-wide trick-or-treating, balloon animals, an interactive magic show and a costume contest with prizes.  

“Keiki Halloween is one of our favorite traditions at The Shops at Wailea because it brings together families from Maui and around the world for an afternoon of fun,” said Diana Whitt, General Manager and Vice President of Property Management at The Festival Companies, the management and leasing firm for The Shops at Wailea. “Every year, our guests surprise us with their creativity, and seeing keiki, ‘ohana and even pets dressed in costume strolling through our Center is such a treat.”

Keiki Halloween Schedule

Festivities will take place throughout The Shops at Wailea, with activities including:

  • 3-7 p.m. | Center-Wide Trick-or-Treating – Keiki (children) can collect treats from participating merchants throughout the Center, identified by balloons.
  • 2-4 p.m. | On-Site Costume Contest Registration – Participants can register on-site the day of the event or in advance via Eventbrite by Wednesday, Oct. 21 at noon. One costume and one category entry is permitted per contestant.
  • 3-5 p.m. | Balloon Animals – Guests can stop by the Middle Valley in front of Rip Curl for complimentary balloon animals.
  • 3:30-4:30 p.m. | Magic Show – Local favorite Brenton Keith & His Bag O’ Tricks takes the stage at the Lower Level Performance Area for an interactive performance featuring comedy and magic.
  • 5-6:30 p.m. | Keiki and Pet Costume Contest – Contestants take the stage in divisions for ages 0-2, 3-5 and 6-10, as well as families and pets.
  • 6:30-7 p.m. | Costume Contest Awards – Local judges will announce first, second and third-place winners in each division and present prizes.

Costume Contest and Grand Prize

Participants are encouraged to show off their most creative, whimsical or spooky looks, with one costume and one category entry permitted per contestant. The grand prize winner will receive two flight vouchers valid on any Alaska Airlines or Hawaiian Airlines-operated flight between Hawaiʻi and North America.

Before or after the festivities, guests can explore more than 80 retailers, restaurants and galleries throughout The Shops at Wailea, making Keiki Halloween part of a full afternoon or evening of shopping, dining and entertainment. For more information and event updates, visit theshopsatwailea.com.

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