Maui Arts & Entertainment

Zoë Eisenberg’s drama “Chaperone,” which won the 2024 Slamdance Grand Jury Award for Best Breakout and features an entirely AANHPI cast, is set to screen in select theaters across the islands Sept. 11–28, 2025, followed by a nationwide digital debut Oct. 3, 2025. 

The Hawai’i Tourism Authority has awarded $980,000 in funding to 26 community-based organizations through its Kūkulu Ola program, as part of its commitment to supporting and strengthening Native Hawaiian culture by providing genuine experiences for residents and visitors statewide. 

From Oct. 17 to Nov. 2, 2025, Maui audiences are invited to experience a high-energy production of “The Rocky Horror Show” live at the Historic ʻĪao Theater. The show stars award-winning musician, actor, and entertainer Eric Gilliom, who has announced that this will be his final reprise of the iconic Dr. Frank N. Furter role.

The Henry Kapono Foundation has announced the launch of the Home in the Islands Music Festival 2025, a month-long celebration of Hawai‘i’s music, culture and community throughout September.

The Maui Arts & Cultural Center will present Satoru Abe: Reaching for the Sun, an exhibition showcasing over seven decades of work by one of Hawai‘i’s most prominent artists, from Sept. 16 to Nov. 22, 2025, at the Schaefer International Gallery.

The Lahaina Restoration Foundation announced that tickets are still available for the September showing of E Hoʻi Ka Nani I Mokuʻula (Let the Glory Return to Mokuʻula). Tickets go quickly, so this is a wonderful and rare, last-minute opportunity, organizers said.

A Special Fair Day for residents with intellectual and developmental disabilities, mobility impairment and members of the Deaf community will be held from 10 a.m. to 1 p.m. Friday, Oct. 3, 2025, as part of the Maui County Fair. The event at the War Memorial Special Events Complex will include rides, games and live entertainment.

This seven-workshop series, running Sunday evenings from Sept. 21 through Nov. 16 at FUZZ BOX Studios, is designed to help participants build skills, gain confidence, and discover new passions under the guidance of industry professionals.

The Montessori School of Maui will host the return of its signature fall fundraiser, Taste of Upcountry, on Saturday, Sept. 13, from 6 to 10 p.m. at the school’s nine-acre campus in Makawao.

The popular, longtime Healthy Baby Contest will return to the Maui County Fair at 11 a.m. Saturday, Oct. 4, 2025, on the War Memorial Special Events Complex entertainment stage.

The Slack Key Show, Maui’s longest-running weekly concert series announced a special performance featuring two extraordinary Hawaiian musicians: ʻukulele virtuoso Brad Bordessa and master slack key guitarist Kevin Brown, hosted by the Shem Kahawaii.

Aloha Festivals announced its 2025 Royal Court. Maui events run from Sept. 5 through Oct. 26.

Outrigger Kāʻanapali Beach Resort invites guests and the community to immerse themselves in two deeply rooted cultural experiences this fall: the Kauluhiwaolele Maui Fiber Arts Conference (Sept. 11-13, 2025) and Hula O Nā Keiki, the coveted children’s hula competition (Oct. 10-11, 2025).

The public is invited to help create artwork for the County of Maui’s Wailuku Garage from 5:30 to 9 p.m. in front of Historic ʻĪao Theater as part of Wailuku First Friday on Sept. 5, 2025.

This Saturday, Sept. 6, the community will gather for Lights for Lahaina, an evening dedicated to reflection, healing, and the enduring spirit of Lahaina. From 4 p.m. to 9 p.m., the historic grounds of Maria Lanakila Catholic Church will be transformed into a space where Maui’s ʻohana can come together to honor the past and embrace hope for the future.

The Hawaiʻi State Foundation on Culture and the Arts announces a calendar of upcoming exhibits at Capitol Modern: the Hawaiʻi State Art Museum. The exhibits include collaborations with World Wide Walls and the Maui Arts and Cultural Center, and a display of recently acquired artworks for the SFCA Art in Public Places Collection.

The Shops at Wailea continues its tradition of complimentary entertainment this September with a diverse lineup at the Lower Level Performance Area—plus weekly community wellness.

Former Mayor Michael Victorino will lead the Maui County Fair Parade as Grand Marshal, according to an announcement by Mayor Richard Bissen. The iconic parade starts at 4:30 p.m. Thursday, Oct. 2, 2025, in Kahului, marking the start of the four-day 98th Maui County Fair.

Maui artists Matt Agcolicol and Bailey Onaga teamed up with students from MEO’s Youth Services program to paint “Oneloa & Keoneʻōʻio” on a Kūihelani Highway sound wall in Kahului.

The 8th Annual Hawaiʻi Salsa & Bachata Paradise is set to bring the rhythm, energy and passion of Latin dance back to Honolulu from Thursday, Aug. 28 through Sunday, Aug. 31, 2025.