The Top 5 Events on Maui for May 2026
- Maui Brewers Festival (May 16) – One of Maui’s top annual events, featuring craft beer tastings, free food from 25+ local vendors, live music, and a lively social atmosphere at the MACC.
- CIRCA: Humans 2.0 (May 3) – A visually stunning, high-energy performance blending acrobatics, music, and light into one of the most unique shows of the year.
- Flamingosis Live in Paia (May 2) – An intimate North Shore performance featuring funk, soul, and electronic grooves in a fully immersive setting.
- Maui Matsuri Festival (May 9 & 23) – A two-part cultural celebration with keiki-focused activities and a larger evening festival showcasing food, performances, and Japanese traditions.
- LEI KAULANA Hula Presentation (May 31) – A beautiful afternoon of Hawaiian music and hula honoring the cultural significance of lei through song and dance.
Aloha May 2026, and welcome back to your hand curated Maui monthly calendar of events! As we move deeper into spring, the island hits a perfect stride. Longer days, warm trade winds, and a full calendar of events that bring together culture, community, and entertainment. From Lei Day celebrations and world-class performances to live music, food festivals, and opportunities to give back, May offers something for everyone across the Valley Isle.
The Debut of Waiakoa: A Lei Day Celebration (May 1, 2026)
There’s no better way to begin the month of May on Maui than by celebrating one of Hawai‘i’s most meaningful traditions. Lei Day, observed annually on May 1st since 1928, honors the lei as a symbol of aloha, love, respect, and connection. Across the islands, communities come together through music, hula, and storytelling to reflect on the cultural significance of this timeless practice, and this year, Maui has a very special way to mark the occasion.
Head to ProArts Playhouse in Kīhei for the debut of Waiakoa, a new musical trio led by Anthony Pfluke alongside Tarvin Makia and Ethan Villanueva. This intimate evening blends live music with talk story, offering a deeper look into the history and meaning of the lei through song and shared experience. It’s a thoughtful and engaging way to connect with Hawaiian culture in a setting that feels both personal and meaningful.
- When: Friday, May 1, 2026 – 7:30 PM
- Where: ProArts Playhouse, 1280 S Kihei Rd, Kihei, HI 96753
- Run Time: 105 minutes (with intermission)
- Tickets: Required, available for purchase online here
- More Info: ProArts Playhouse – Waiakoa Lei Day Celebration
Flamingosis Live in Paia (May 2, 2026)
If you’re looking for a different kind of nightlife experience on Maui, this is one to have on your radar. Flamingosis brings his signature blend of funk, soul, and analog warmth to the North Shore for a one-night-only performance in Paia. His sound is built on feel and movement, blending crate-dug samples with live instrumentation to create something that feels both nostalgic and fully alive in the moment. With over 100 million streams and a global following, Flamingosis has carved out a unique lane where laid-back listening meets full-body motion.
Set inside the intimate space at Paia Bay Coffee Bar, this show is all about energy and atmosphere. A full Meyer Sound system paired with Unity Lasers transforms the venue into an immersive environment where every beat lands with clarity and depth. Capacity is limited, so arriving early is key. For those who appreciate music, sound design, and a more curated live experience, this is one of the more unique nights happening on Maui this month.
- When: Saturday, May 2, 2026
- Where: Paia Bay Coffee & Bar, 120 Hana Hwy, Paia, HI 96779
- Tickets: Pre-sale available online for $45 here
- Details: 21+ only. Valid ID required
- More Info: Presented by Neon Nomad
CIRCA: Humans 2.0 (May 3, 2026)
If you’re looking for something truly different this month, CIRCA: Humans 2.0 brings a world-class performance to Maui that pushes the limits of what live entertainment can be. Hosted at the Maui Arts & Cultural Center, this internationally acclaimed production blends acrobatics, sound, and lighting into a visually stunning and physically demanding experience.
The performance features ten performers moving in sync, building and breaking formations, testing balance, strength, and connection in real time. Set to a pulsing score and dramatic lighting, the show explores themes of human connection and adaptability. Whether you’re drawn to dance, theater, or high-level athleticism, this is one of the most unique performances you’ll see on Maui this year.
- When: Sunday, May 3, 2026 – 7:30 PM
- Where: Castle Theater, Maui Arts & Cultural Center, 1 Cameron Way, Kahului, HI 96732
- Tickets: $27, $47, $67, $87 and available online here
- More Info: Maui Arts & Cultural Center – CIRCA
Aloha Veggies Book Signing w/ Alana Kysar (May 8, 2026)
For a more relaxed and community-centered event, this is a great way to spend an afternoon in Lahaina. Hana Hou by Hale Zen will be hosting a book signing with Maui-based author and Seabury Hall alumni, Alana Kysar, celebrating the release of her newest cookbook, Aloha Veggies.
This casual, open-to-the-public gathering gives you the chance to meet the author, talk story, and get your books signed while enjoying complimentary pūpū. Whether you’re passionate about cooking or simply enjoy supporting local creatives, it’s a meaningful way to connect with Maui’s culinary community.
- When: Friday, May 8, 2026 – 4PM to 6PM
- Where: Hana Hou by Hale Zen, 157 Kupuohi St Suite J4, Lahaina, HI 96761
- Tickets: Free but be sure to reserve your spot via Eventbrite and buy the Aloha Veggies book online here
- More Info: Hana Hou by Hale Zen
Maui Matsuri 2026: Children’s Festival & Japanese Festival (May 9 & May 23, 2026)
Maui Matsuri returns this May with two community-driven events that celebrate culture, connection, and the spirit of friendship. These events highlight the rich cultural ties that continue to shape life on Maui, offering something meaningful for all ages.
The Children’s Festival on May 9 focuses on keiki, with hands-on activities, crafts, and interactive learning experiences. Later in the month, the Japanese Festival on May 23 expands into a larger evening celebration featuring live entertainment, food vendors, cultural exhibits, and community activities, including bon dancing as the sun sets.
- Children’s Festival : Saturday, May 9, 2026 – 10AM to 1PM
- Japanese Festival: Saturday, May 23, 2026 – 3PM to 9:00PM (Obon from 7:30-9PM)
- Where: University of Hawaiʻi Maui College (Central Maui)
- Tickets: Free
- More Info: Maui Matsuri
Ukumehame Beach Cleanup with Surfrider Maui and Mālama Maui Nui (May 16, 2026)
If you’re looking for a way to give back while enjoying a morning by the ocean, this beach cleanup along Ukumehame is a great opportunity to get involved. Hosted by Surfrider Foundation Maui in partnership with Mālama Maui Nui, the focus is on cleaning up debris before it enters the ocean.
Volunteers meet near Mile Marker 13 and can choose which section of beach to mālama. Gear is provided, and the vibe is relaxed and community-driven. It’s a simple, impactful way to support Maui’s coastline while connecting with others who care about the island.
- When: Saturday, May 16, 2026 – 9AM to 11AM
- Where: Ukumehame Beach Park, 615 HI-30, Lahaina, HI 96793
- Registration: Online here
- More Info: Surfrider Foundation Maui
Maui Brewers Festival at the MACC (May 16, 2026)
One of Maui’s most anticipated annual events returns to the Maui Arts & Cultural Center with an afternoon full of craft beverages, local food, and live music. Guests can enjoy tastings from breweries and distilleries alongside complimentary food from over 25 local vendors, with this year’s featured culinary showcase centered around poke.
The “Beer Lover” ticket offers early entry and VIP-style access, while General Admission still delivers a full experience with tastings, entertainment, and plenty of food. With live music and a lively crowd, this is one of the most fun and social events of the month.
- When: Saturday, May 16, 2026 / Beer Lover Entry: 2PM / General Admission: 3:30PM – 7PM
- Where: Maui Arts & Cultural Center, 1 Cameron Way, Kahului, HI 96732
- Tickets: General Admission: $98 / Beer Lover: $163 / Designated Driver options available
- More Info: Maui Arts & Cultural Center
LEI KAULANA: A Hula Presentation (May 31, 2026)
Close out the month with a celebration of Hawaiian culture through music and hula at LEI KAULANA. Led by award-winning Kumu Hula Kamaka Kukona, this performance brings together song, dance, and storytelling in a way that feels both authentic and deeply moving.
Centered around the significance of lei, the show weaves together themes of aloha, connection, and the natural beauty of the islands. Featuring talented musicians and hula practitioners, this is a meaningful way to experience the traditions that continue to define Hawai‘i.
- When: Sunday, May 31, 2026 – 2PM
- Where: Castle Theater, Maui Arts & Cultural Center, 1 Cameron Way, Kahului, HI 96732
- Tickets: General Admission is $56 and available online here
- More Info: Maui Arts & Cultural Center
Contact a Maui Real Estate Specialist
April on Maui is a reminder that you don’t need “one big festival week” for the island to feel alive—sometimes the magic is spread across concerts, community nights, cultural gatherings, and one perfect Sunday brunch. Mark your favorites, leave yourself some breathing room, and enjoy the month the Maui way: show up, talk story, and let the days surprise you.
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