Families across Maui can mark their calendars for Saturday, Oct. 24, when The Shops at Wailea throws open its center for Keiki Halloween, a free, all-ages celebration running from 3 to 7 p.m. There's no cost and no ticket required just to attend, with center-wide trick-or-treating, balloon animals, a comedy and magic show, and a costume contest all on the schedule.
The event, detailed by Maui Now, keeps the same family-oriented format that has become a fixture at the outdoor shopping center in recent years. Trick-or-treating runs the full four hours, letting kids collect treats from participating merchants marked by balloons. According to the event listing on theshopsatwailea.com, the celebration is free for all ages and does not require registration or tickets to attend, though contestants in the costume contest do need to sign up separately.
A Full Afternoon of Entertainment
Balloon animals will be available from 3 to 5 p.m. in the Middle Valley area in front of Rip Curl, while Brenton Keith & His Bag O' Tricks takes the lower-level performance area for an interactive comedy and magic show from 3:30 to 4:30 p.m. Both attractions take place during the 3–7 p.m. trick-or-treating window.
The keiki and pet costume contest is the afternoon's centerpiece. Registration runs from 2 to 4 p.m. on event day, the contest itself from 5 to 6:30 p.m., and awards from 6:30 to 7 p.m. Divisions cover ages 0–2, 3–5 and 6–10, along with an ʻohana family category; contestants entering with a pet should select the ʻOhana category. Each contestant may enter one costume in one category. Local judges will announce first-, second- and third-place winners in each division and hand out prizes on the spot.
Flight Vouchers on the Line
The overall grand prize this year includes two flight vouchers valid on Alaska Airlines- or Hawaiian Airlines-operated flights between Hawaiʻi and North America, which must be booked by Oct. 13, 2027, per the official event page. That builds on past years' grand prizes, which the Wailea Resort Association has described as two round-trip Alaska Airlines tickets.
“Keiki Halloween 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 for The Festival Companies, the management and leasing company for The Shops at Wailea. Whitt also said guests dress up keiki, ʻohana and pets, and their creativity surprises the center each year.
A Growing Tradition at the Center
Keiki Halloween has drawn roughly 1,000 guests in each of the past two years. The 2025 event drew 1,000 guests, and the 2024 celebration drew nearly 1,000 guests with 180 contestants taking part in that year's costume contest. A 2026 attendance projection was not available ahead of this year's event.
Last year's grand prize went to Cayman and Tania Woessner, who won for their Predator and Spawn costumes, continuing a tradition of elaborate family and ʻohana entries at the center. The Shops at Wailea includes more than 80 retailers, restaurants and galleries, giving the event plenty of ground to cover for trick-or-treaters moving between storefronts.
