May on Maui is a time of renewal, connection, and celebration. From time-honored cultural traditions to lively music festivals and community fundraisers, the island comes alive with events that reflect the aloha spirit and the diversity of our community. Whether you're stringing flowers on Lei Day, enjoying classical music in historic churches, or sipping craft beer under the stars, there's something for everyone to experience.
May 1 – Lei Day Celebrations
Various locations across Maui
All day
Lei Day is a cherished Hawaiian tradition celebrated annually on May 1st. Established in 1929, the day honors the cultural significance of the lei, symbolizing love, friendship, and the aloha spirit. Festivities include lei-making workshops, hula performances, and the selection of Lei Day courts representing each island. Maui's official lei flower is the pink lokelani rose, reflecting the island's unique identity.
Lei Day Heritage Festival at Hale Hōʻikeʻike (Bailey House Museum)
2375A Main Street, Wailuku
May 1, 2025, 10:00 AM – 3:00 PM
Hosted by the Maui Historical Society, this festival offers lei-making workshops, live music, cultural demonstrations, and a lei contest featuring categories such as fresh floral, natural materials, and recyclable leis. Attendees can immerse themselves in the art of lei-making and enjoy local food offerings.
May 10 – Seabury Hall Craft Fair
Seabury Hall, 480 Olinda Rd, Makawao
9:00 AM – 4:00 PM
The Seabury Hall Craft Fair is a beloved Upcountry Maui tradition that draws residents and visitors alike. The fair features over 100 local artisans showcasing handcrafted jewelry, ceramics, textiles, and traditional Hawaiian arts. Guests can enjoy live music, gourmet food vendors, a silent auction, and a variety of keiki-friendly activities. Proceeds support Seabury Hall’s financial aid programs, helping to expand access to quality education for Maui’s youth.
May 10 – 46th Annual Visitor Industry Charity Walk
War Memorial Special Events Arena, Wailuku
7:30 AM Registration & Coffee | 8:00 AM Walk Begins | 8:30 AM Festivities
Organized by the Maui Hotel & Lodging Association, this 2.5-mile walk is Hawai‘i’s largest single-day fundraising event by a nonprofit organization. Since its inception, over $42.8 million has been raised statewide, with Maui County contributing $1.6 million in 2024 alone. The event features live entertainment, breakfast, and prize drawings, all while supporting local charities.
May 11 – Anuhea Live at da Playground Maui
da Playground Maui, 300 Maalaea Road, Wailuku
Doors open at 6:00 PM; Show starts at 7:00 PM
Celebrate Mother’s Day weekend with Hawai‘i’s own songbird, Anuhea, as she performs live at da Playground Maui. Known for her soulful voice and blend of reggae, pop, and R&B, Anuhea will be joined by special guests, The Office Ladies. This 21+ event promises an evening of heartfelt music and island vibes.
May 16–25 – Maui Classical Music Festival
Makawao Union Church, ʻĪao Theater, and other venues
Celebrating its 43rd year, the Maui Classical Music Festival brings together world-class musicians for a series of chamber music concerts in historic venues across the island. The festival offers intimate performances, educational outreach, and community engagement, enriching Maui's cultural landscape with classical artistry.
Program Highlights:
Friday, May 16 – "Baroque to Brilliance"
Makawao Union Church, Makawao – 7:00 PM
Monday, May 19 – "Haunting to Heroic"
Keawalaʻi Congregational Church, Makena – 7:00 PM
Wednesday, May 21 – "Hāna Community Concert"
Wananalua Congregational Church, Hāna – 6:00 PM
Friday, May 23 – "Love Triangle, Beethoven and Schumann"
The Historic ʻĪao Theater, Wailuku – 7:00 PM
Sunday, May 25 – "Festival Finale"
The Historic ʻĪao Theater, Wailuku – 4:00 PM
For more details and ticket information, please visit the official website: Maui Classical Music Festival.
May 17 – Maui Brewers Festival
Maui Arts & Cultural Center, Kahului
3:30 PM – 7:00 PM
The Maui Brewers Festival is a premier event featuring craft beer tastings from local and national breweries, complemented by gourmet food from Maui's top chefs. Live music performances and oceanfront views enhance the festive atmosphere. Proceeds benefit the Maui Arts & Cultural Center's arts education programs, supporting creativity in the community.
May 17-18 – Menehune Mayhem
Ho‘okipa Beach Park, Pā‘ia
All day
Menehune Mayhem is a free, family-friendly surf competition dedicated to Maui's keiki. Beyond the waves, the event promotes Hawaiian values, environmental stewardship, and healthy lifestyles. Participants engage in cultural activities, educational workshops, and community service projects, fostering a sense of responsibility and connection to the ʻāina (land).
May 22 – Artist 2 Artist: Henry Kapono & Hawaiian Style Band
McCoy Studio Theater, Kahului
7:00 PM
Join Grammy-nominated musician Henry Kapono as he hosts an intimate concert featuring the Hawaiian Style Band. The evening includes storytelling, collaborative performances, and insights into the artists' creative journeys, offering a unique glimpse into Hawai‘i's contemporary music scene.
May 24 – Nashville Nights: Love and Theft
Hyatt Regency Maui Resort and Spa, Lahaina
7:00 PM
Experience the sounds of country music duo Love and Theft in an intimate setting at the Hyatt Regency Maui. The Nashville Nights series brings mainland musical talent to the islands, creating cross-cultural connections through shared musical experiences.
May 24 – Sharks After Dark: Reggae Night
Maui Ocean Center, 192 Māʻalaea Road, Wailuku
6:00 PM - 9:00 PM
Experience an island-inspired 21+ evening at the Maui Ocean Center's "Sharks After Dark: Reggae Night." The event features live reggae music, delicious food and drinks, diver presentations, and screenings of the “Humpbacks of Hawai’i” 3D experience.