June on Maui is a sweet spot — the island is lush from spring rains, the ocean has settled into its clearest summer blue, and the trade winds keep things comfortable well into the evening. It is also one of the busiest months on the cultural calendar, with free outdoor films, a royal parade, world-class concerts, and festivals that have been drawing locals and visitors alike for decades. Whatever brings you to the Valley Isle this month, there is something worth showing up for.

Starry Night Cinema: Zootopia 2 & Lilo and Stitch

Fri June 5 & Sat June 6, 2026 · Gates 6:00 pm, Film 7:30 pm each night

A&B Amphitheater Lawn / Castle Theater, MACC, Kahului

The MACC's Starry Night Cinema series kicks off the month with two back-to-back

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

If March had you watching the rain from your lanai, April is your reward. The weather softens, the sun shows up reliably, and Maui's event calendar fills up fast. Whether you're in the mood for a gala, a road race, a cultural festival, or a night of stand-up comedy, there's something happening this month worth getting off the couch for. Here's a look at some of the best events coming up across the island.

Imua Ball: PANDAmonium! The Shanghai Swing Festival

Saturday, April 4, 2026

Hyatt Regency Maui Resort & Spa, Kaʻanapali

5:30 PM – Chinatown Marketplace Cocktail Reception | 6:50 PM – Ballroom Doors Open

Step into the glittering energy of old-school Shanghai at PANDAmonium: Shanghai Swing Festival, Imua Family Services'

March on Maui arrives with momentum — a month where shoreline races, concert halls, fairways, and cultural gardens all find their rhythm. Early mornings begin along the coast with steady footsteps and salt air, while evenings shift indoors to stages alive with music, storytelling, and laughter. Across the island, the calendar fills with experiences that move seamlessly from oceanfront courses to theater seats and open-air cultural spaces. The season carries a natural balance of energy and ease — offering meaningful ways to engage with Maui’s community throughout the month.

Maui 5K Run & Walk

Sunday, March 1, 2026
Māʻalaea / Wailuku

March opens with movement. The Maui 5K is a long-standing community road race offering a 5-kilometer run, a

February arrives on Maui with a layered rhythm of culture, creativity, and seasonal wonder. As humpback whales migrate through warm island waters and winter light softens the landscape, communities across the island gather to mark renewal, heritage, and artistic expression. Lunar New Year celebrations bring color and movement to town centers, while painters, musicians, chefs, scientists, and storytellers offer intimate windows into their craft. From gallery openings and live performances to plein air painting, culinary festivals, and ocean-focused conservation events, this month’s calendar reflects Maui as both a living cultural crossroads and a place deeply shaped by nature.

Gutenberg! The Musical!

January 30-31, February 1, 5–8, and