May on Maui belongs to the kama'āina — the humpbacks have headed back to Alaska, the visitor crowds are still thin, and the island fills its calendar with the kind of events that remind you exactly why you live here. From Lei Day celebrations to surf contests, craft fairs to cultural performances, there's something worth showing up for almost every day, and some weekends you'll have to choose.
Lei Day on Maui
May 1, 2026
Hale Hōʻikeʻike at the Bailey House, Wailuku
May Day is Lei Day in Hawaiʻi, and one of the most beloved celebrations on the island happens right in the heart of historic Wailuku. The Maui Historical Society's Lei Day Heritage Festival transforms the peaceful grounds of the Bailey House into a living celebration of Hawaiian culture — mele Hawaiʻi, hula, hands-on lei making, and cultural demonstrations, all free and open to the whole ʻohana. It's unpretentious, deeply rooted, and the kind of community event that reminds you exactly why you live here. Make a day of it — Maui does Lei Day like nowhere else.
Gary Owen: No Hard Feelings Tour
May 1, 2026 · 7:30 PM
Maui Arts & Cultural Center, Kahului
Cap off Lei Day with a night of laughter on the MACC stage. Gary Owen is one of America's most consistently funny touring comedians — sharp, high-energy, and genuinely hilarious — and this is the kind of show that reminds you how good it feels to just sit back and laugh with a room full of strangers. Grab tickets before they're gone.
HHSAA State High School Surfing Championship
May 1–2, 2026
Ho'okipa Beach Park, North Shore
This one is history in the making. For the first time ever, surfing is an official interscholastic state championship sport in Hawaiʻi — and Maui's own Hoʻokipa Beach Park is hosting the inaugural event. Watch the next generation of Hawaiian surfers compete across shortboard, longboard, and bodyboard divisions, carrying forward a tradition that runs as deep as the ocean itself. Free to attend — check the details at hhsaa.org and make the drive to the North Shore.
CIRCA Humans 2.0
May 3, 2026 · 7:30 PM
Maui Arts & Cultural Center, Kahului
Australia's extraordinary CIRCA company returns to Maui with Humans 2.0 — a breathtaking physical theater experience that uses acrobatics to ask what it really means to be human. Expect gasps, silence, and a standing ovation. This is the kind of live performance that stays with you for weeks, the sort that reminds you why leaving the couch is always, always worth it.
Cinco de Mayo at Lahaina Cannery
May 5, 2026
Lahaina Cannery, West Maui
This one carries extra meaning this year. For the first time since the Lahaina fires, the Cinco de Mayo festivities at Lahaina Cannery are bringing joy, culture, and celebration back to the Front Street area — a neighborhood that has worked so hard to reclaim its spirit. A great excuse to head to West Maui and celebrate.
Starry Night Cinema: The Little Mermaid
May 8, 2026 · 7:30 PM
Maui Arts & Cultural Center, Kahului
There is something especially right about watching The Little Mermaid outdoors on an island surrounded by the Pacific. MACC's Starry Night Cinema series brings movies under the open sky, and this one is perfect for families, date nights, or anyone who wants to sing along with the trade winds blowing through. Bring a blanket, arrive early for a good spot, and enjoy one of those simple, perfect Maui evenings.
Seabury Hall Craft Fair
May 9, 2026 · 9:00 AM–4:00 PM
Seabury Hall, 480 Olinda Rd, Makawao, Upcountry Maui
Fifty years in and still one of the best days on the Upcountry calendar. The Seabury Hall Craft Fair brings together Maui's finest artisans, jewelers, crafters, and floral designers for a vibrant open-air marketplace on the school's beautiful Makawao campus. Proceeds support financial aid programs, so every purchase does double duty — and with live music, local food, and a silent auction, it's an easy way to spend a beautiful May morning. Admission is $10 for adults; keiki under 12 get in free.
Maui Brewers Festival — 15th Anniversary
May 16, 2026 · 2:00 PM
Maui Arts & Cultural Center, Kahului
Fifteen years of great beer, great company, and one of the best afternoons on Maui's event calendar. The Maui Brewers Festival brings together local and national craft breweries for a day of tasting and live music on the MACC grounds. The 15th anniversary edition promises to be the best yet — raise a glass to a decade and a half of this beloved island tradition.
Ian Walsh Menehune Mayhem
May 16–17, 2026
Ho'okipa Beach Park, North Shore
Hoʻokipa hosts another beloved community event — the Ian Walsh Menehune Mayhem youth surf contest, now in its 21st year. This free two-day event is pure Maui: keiki charging waves, families cheering from the sand, and a community rallying around the next generation of surfers. Come for the surfing, stay for the spirit of the whole thing.
Maui Matsuri Japanese Festival
May 23, 2026 · 10:00 AM–9:00 PM
University of Hawai'i Maui College, Kahului
One of Maui's most festive annual cultural celebrations, the Maui Matsuri Japanese Festival fills the UHMC campus with free entertainment, keiki crafts, food booths, eating contests, and traditional Bon dancing as evening falls. It's a joyful, multigenerational event that reflects the deep Japanese cultural roots woven into the fabric of this island — and the food alone is worth showing up for.
Lei Kaulana
May 31, 2026 · 2:00 PM
Maui Arts & Cultural Center, Kahului
Close out the month with something quietly beautiful. Lei Kaulana is a celebration of Hawaiian culture through the sacred art of lei — performance, tradition, and community woven together on the MACC stage. It's a fitting way to end a month that began with Lei Day: a reminder that in Hawaiʻi, the lei is never just a flower. It's a greeting, a farewell, an expression of love, and a thread that connects us all.