May is an excellent time to be on Maui. When you’re not out enjoy Maui’s stunning springtime weather and golden beaches, stop by one of this month’s concerts, cultural festivals, and community events!
What’s Happening on Maui for May 2026?
Live music is still happening around the island, with local musicians jamming almost every night at some of the island’s best restaurants. Check out Mana’o Radio’s Music2Nite site for a full lineup of Live Music on Maui.
Maui Events May 2026
May 1
Wailuku First Friday: Wailuku First Friday is a lively street party held on the first Friday of each month in historic Wailuku Town. Enjoy live music, food trucks, local vendors, and keiki activities along Market Street. Free and open to all!
Gary Owen: No Hard Feelings Tour: Gary Owen has been entertaining audiences for more than two decades with his sharp observational humor and fearless storytelling. Following a wave of record-breaking, sold-out performances at comedy clubs across the country, Gary Owen brings his first major North American theater tour, NO HARD FEELINGS to Maui! Maui Arts and Cultural Center, 7:30 pm.
Lei Day Heritage Festival: Join the Maui Historical Society for a Lei Day celebration with interactive exhibits, cultural demonstrations, and special events. This event explores the origin of Hawaii’s cherished lei tradition. Come celebrate! Bailey House Museum, 10:00am – 4:00 pm.
The Debut of Waiakoa: A Lei Day Celebration: Join Waiakoa, Maui’s newest musical trio, for a special Lei Day debut. Get to know Waiakoa and learn about the history and significance of lei through music and talk story. Pro Arts Playhouse, 7:30 pm.
May 3
Circa Humans 2.0: Created by circus visionary Yaron Lifschitz, Humans 2.0 is intimate, primal, and deeply engaged with the challenge of being human. This next chapter of Circa’s internationally acclaimed Humans is a tightly woven choreography of bodies, pulsing with music by composer Ori Lichtik and revealed in Paul Jackson’s dramatic lighting. Maui Arts and Cultural Center, 7:30 pm.
May 6
John Cruz: Island Style Series: Come check out Nā Hōkū Hanohano Award-winner John Cruz at home in his element – performing live in a premier listening room where you see, hear and feel every note! At ProArts Maui, every attendee gets to fully tap into Cruz’s talent and spirit and embrace the power of love, compassion and common ground. Pro Arts Playhouse, 7:00 pm.
May 8
Maui Classical Music Festival Opening Day: The 44th Annual Maui Classical Music Festival runs from May 8-17, 2026, featuring world-class chamber music performances at iconic venues across the island, including Makawao Union Church and Iao Theater. Don’t miss this chance to experience exceptional classical music in Maui’s most historic settings. Visit their website for more info.
Starry Night Cinema: The Little Mermaid: The Maui Arts and Cultural Center presents another Starry Night Cinema event! Bring a low-back beach chair and/or a blanket and spread out on the lawn for a special screening of Little Mermaid. Free event! MACC, 6:00 pm.
May 9
Maui Matsuri Children’s Festival: Maui Matsuri started as a Japanese festival on Market Street in Wailuku Maui in May 1999. The focus is to provide an environment for families to share and learn about Japanese culture and pass down traditions. Don’t miss the Children’s Festival with multi-cultural entertainment, crafts, and hands-on activities. UH Maui College, 10:00am – 1:00 pm.
Mini KISS: MINI KISS, a KISS cover band made up entirely of little people, is coming for the first time ever to Hawaii to rock like never before! Experience the electrifying energy of KISS – with a twist – as Mini Kiss brings their legendary tribute show live to da Playground. da Playground Maui, 7:00 pm, 21+.
Seabury Hall Craft Fair: Mark your calendars for the 50thh Annual Seabury Hall Craft Fair. This beloved Upcountry tradition features over 100 local artisans, live music, delicious food, keiki activities, a silent auction, and more—all set against the scenic backdrop of Seabury Hall’s campus. Admission is $10 for adults; children under 12 enter free. Proceeds support the school’s financial aid programs.
May 14
Josh Heindricks: Josh Heindricks returns to Maui! Prepare for an evening filled with soulful reggae as he takes the stage live at da Playground. Known for his smooth vocals, this show promises a night of unforgettable music and positive energy. da Playground Maui, 7:00 pm, 21+.
May 16
Menehune Mayhem: Menehune Mayhem is a free keiki surf event – with a twist. Non-competitors can come enjoy the festivities, with educational booths, games, and live performances. Runs May 16-17. Ho‘okipa Beach Park.
2026 Maui Brewers Festival – 15th Anniversary: The MACC’s annual fundraising event—the Maui Brewers Festival—is one of Maui’s top festivals. The event features FREE tasty food from local restaurants and caterers, beer tastings from local and national craft breweries & distilleries, live music, and lots of fun! Musical acts this year are Tavana, DJ Hapa Boy, and Nuff Sedd! Maui Arts and Cultural Center, 2:00 pm.
May 22
Wavvy: Honolulu’s rising wave Wavvy is heading to da Playground for a night of island vibes and feel-good sounds that you won’t want to miss. Blending island reggae with R&B, Wavvy brings a new kind of sound that’s topping charts across Hawaii radio. da Playground, 8:00 pm, 21+.
May 23
Maui Matsuri Japanese Festival: Maui Matsuri started as a Japanese festival on Market Street in Wailuku Maui in May 1999. The focus is to provide an environment for families to share and learn about Japanese culture and pass down traditions. Don’t miss the Japanese Festival, with entertainment, food booths, bon dancing, and more. UH Maui College, 3:00 pm – 9:00 pm.
May 30
Maui Ag Fest: Come celebrate agriculture on Maui! Ag Fest features food booths, a pancake breakfast, a 4H fair, live entertainment, activities, and so much more. Don’t miss the Grand Taste Event, where local chefs create competitive tasting dishes featuring one local ingredient. War Memorial Special Events Field.
May 31
Lei Kaulana: Award-winning Kumu Hula, Grammy-Nominated & two-time Nā Hōkū Hanohano Male Vocalist of the Year, Kamaka Kukona, along with Nā Kumu Hula Jaydon Isobe and Koakāne Mattos, present Lei Kaulana — a magical afternoon of Hawaiian song and dance. This performance, based around all the beautiful floral garlands, or Lei of the islands, will also showcase some of Hawaii’s wonderful musical talents. Maui Arts and Cultural Center, 2:00 pm.
Weekly Events
Mondays
Lei Po’o Making: The Shops of Wailea invites guests to learn how to weave ti leaf leis using ferns and flowers. Lei Po’o can be worn on the head and was typically used as a gift on special occasions by Ali’i (Hawaiian Royalty). This event is open to both keiki and adults and runs from 2:30 to 3:30 pm.
Tuesdays
Polynesian Show at The Shops: This weekly show will highlight Hawaiian hula as well as other dances of Polynesia. The performance will take place at the Shops of Wailea from 5:30 to 6:30 pm.
Coconut Husking at The Shops: From 2:30 to 3:30 pm weekly, the Shops of Wailea will be hosting demonstrations of the traditional and modern methods in husking a coconut. Learn how the Hawaiians would use every part of the coconut from food to crafting eating utensils, jewelry as well as furniture.
Wednesdays
Lei Po’o Making: The Shops of Wailea invites guests to learn how to weave ti leaf leis using ferns and flowers. Lei Po’o can be worn on the head and was typically used as a gift on special occasions by Ali’i (Hawaiian Royalty). This event is open to both keiki and adults and runs from 2:30 to 3:30 pm.
Slack Key Guitar Show: The Masters of Hawaiian Music Slack Key Show is open for live shows once again. The Slack Key Show ohana will perform each week at 6:30 pm at the Napili Kai Beach Resort. Tickets are required for entry, this show is also streamed online.
Thursdays
Coconut Frond Weaving at the Shops: The Shops of Wailea invites guests to try their hand at the highly developed Hawaiian skill of weaving. Coconut frond weaving was used to make baskets, mats, and even toys. This event runs weekly from 4:30 pm to 5:30 pm.
Thursday Night Jams: Come hang at the Plate Lunch Marketplace (you know, the food truck lot across from Costco Gas) and enjoy live music every Thursday night from 6-8 p.m. Don’t forget to pick up an ono smash burger from Haven’s either!
Fridays
Papa Hula at the Shops: Hosted at the Shops of Wailea, Papa Hula is a celebration of the Hawaiian way of life. Enjoy a complimentary dance lesson, complete with costumes and accessories, and the dance movements and their meanings. This interactive performance runs from 4:00 pm to 5:00 pm.
Saturdays
Upcountry Farmers Market: Shop some of the best local souvenirs on the island, indulge in delicious food and support local farmers at one of Maui’s biggest weekly events. Don’t forget to set your morning alarm, as this market favors the early shopper. The Upcountry Farmers Market runs from 7:00 to 11:00 am every Saturday at the Kulamalu Town Center in Pukalani.
Sundays
Maui Gift and Craft Fair: Stop by the Lahaina Gateway Center and browse West Maui’s largest gift and craft fair. This weekly event hosts over 50 vendors, showcasing jewelry, photography, art, crafts, keiki activities, and more. Maui Gift and Craft Fair runs from 9:00 am to 2:00 pm every Sunday.
Maui Sunday Market: Featuring some of Maui’s most renowned food trucks, local vendors, and quality entertainment, the Maui Sunday Market is one of the island’s most popular weekly events. Centrally located at the Kahului Shopping Center, the Maui Sunday Market draws locals and visitors from all corners of the island. The event runs every Sunday from 4:00 pm to 8:00 pm.
For more information or to see the best weekly, monthly, and yearly celebrations, check out our calendar of Upcoming Maui Events.
Mahalo for reading our list of Maui Events May 2026! Have an upcoming event you’d like us to include in the next post? Let us know in the comment section below or contact us directly about how to add your event to our monthly calendar and blog post. Aloha!
Will there be the Maui Jim Shootout the first of June ?