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

South Maui is often experienced through its beaches, sunshine, and easygoing coastal lifestyle…but there’s another side to being here that’s just as meaningful. Across Kihei and Wailea, there are countless ways to connect more deeply with the island through mālama, caring for the land, the ocean, and the community that makes this place home.

For residents and visitors alike, giving back isn’t separate from the Maui experience; it’s part of it. Whether you’re here for a week or a lifetime, there are meaningful ways to step in, connect, and contribute. Below are a few ways to get involved across Kihei and Wailea, with exactly how to start.

Aloha Backpack Buddies (Maui Food Bank)

Supporting local families often begins with something simple: