May is an excellent time to be on Maui. When you’re not out enjoy Maui’s stunning springtime weather and golden beaches, stop by one of this month’s concerts, cultural festivals, and community events! We’ll be sharing more events as they’re announced, so stay tuned. For now, here are the best Maui events in May!
What’s Happening on Maui for May 2025?
Live music is still happening around the island, with local musicians jamming almost every night at some of the island’s best restaurants. Check out Mana’o Radio’s Music2Nite site for a full lineup of Live Music on Maui.
Maui Events May 2025
May 1
Lei Day at Maui Ocean Center: Celebrate Lei Day at the Maui Ocean Center with a day dedicated to the beauty and meaning of Hawai‘i’s iconic flower lei. Explore the rich history of lei-making, create your own lei, and connect with partnering cultural organizations. This hands-on celebration honors the spirit of aloha through storytelling, tradition, and community. 10 am to 3 pm.
Lei Day at Hale Hoikeike: Celebrate Lei Day and all things Hawaiian at the Maui Historical Society’s annual Heritage Festival. Browse stunning leis at the lei competition and enjoy live music and cultural demonstrations like poi pounding and kapa making. The event takes place at the Bailey House Museum from 10 am to 2 pm.
May 2
Wailuku First Friday: Wailuku First Friday is a lively street party held on the first Friday of each month in historic Wailuku Town. Enjoy live music, food trucks, local vendors, and keiki activities along Market Street. Free and open to all!
Kanekoa: Catch Maui’s own Kanekoa live at ProArts for a night of high-energy Hawaiian jam-rock. Known for their electric ukuleles, soulful originals, and legendary covers, this Nā Hōkū Award-winning band blends island vibes with jam band grooves. Don’t miss the group Billboard calls “Hawaiian trailblazers.”
May 3
Lei Po’o Workshop: Create your own stunning lei poʻo at this hands-on workshop led by Caitlyn Madrid of Lei Maui. You’ll learn the wili-style technique using fresh local flowers and raffia. BYOB and enjoy sweeping views of West Maui while crafting a beautiful floral crown to take home. 2:30 pm to 5:30 pm.
May 10
Seabury Hall Craft Fair: Mark your calendars for the 49th Annual Seabury Hall Craft Fair. This beloved Upcountry tradition features over 100 local artisans, live music, delicious food, keiki activities, a silent auction, and more—all set against the scenic backdrop of Seabury Hall’s campus. Admission is $10 for adults; children under 12 enter free. Proceeds support the school’s financial aid programs.
May 11
Anuhea: Celebrate Mother’s Day weekend with Maui’s own Anuhea! With special guests The Office Ladies kicking off the show, this feel-good night blends island vibes, soulful vocals, and heartfelt lyrics. Doors open early for food, drinks, and good vibes.
May 15
Amy Hanaialii: Enjoy an intimate performance with Amy Hānaiali‘i, Hawai‘i’s top-selling vocalist of all time! With 6 Grammy nominations and 18 Nā Hōkū Hanohano Awards, Amy’s powerful voice and rich storytelling have captivated audiences worldwide. Don’t miss this chance to experience the talent of a true Hawaiian music legend!
May 16
Dueling Pianos: Get ready for the ultimate sing-along party with Felix and Fingers Dueling Pianos at Da Playground Maui! This interactive show combines concert vibes, comedy, and your song requests—from Queen to Cardi B to classic rock and Latin jams. Featuring Maui’s own Jake Carter and Leana Courtney, two ridiculously talented performers, this night promises non-stop fun. Come ready to sing, dance, and laugh.
Maui Classical Music Festival Opening Day: The 43rd Annual Maui Classical Music Festival runs from May 16-25, 2025, featuring world-class chamber music performances at iconic venues across the island, including Makawao Union Church and Iao Theater. Don’t miss this chance to experience exceptional classical music in Maui’s most historic settings. Visit their website for more info.
May 17
Maui Brewers Festival: Maui Brewers Festival is one of Maui’s top festivals! Enjoy beer tastings from local and national craft breweries, tasty bites from local restaurants, and live music from Justin Morris & Company, The Roundabouts, and Three to 5. Not a beer fan? Try cold brew coffee, kombucha, or root beer. Must be 21+ with valid ID.
Menehune Mayhem: Menehune Mayhem is an annual, two-day keiki event hosted by professional surfer Ian Walsh. Menehune Mayhem is Maui’s only free keiki surf competition, but there’s a ton of fun for non-competitors too, including an art booth, live music, games, demonstrations, and much more. Check out the action at Ho’okipa Beach Park on May 17 and 18.
May 22
Artist2Artist – Henry Kapono & Hawaiian Style Band: Join Henry Kapono, Bryan Kessler, Wade Cambern, and Robi Kahakalau for a night of legendary Hawaiian music. Enjoy pre-concert entertainment by Arlie Asiu and food & drinks for purchase and talk story with the artists after the show.
May 24
Sharks After Dark: Experience an island-inspired 21+ night at Maui Ocean Center with live reggae music, delicious food and drinks, diver presentations, and screenings of the “Humpbacks of Hawai’i” 3D experience.
May 31
Israel Vibration: Roots reggae legends Israel Vibration bring their tour to Maui, joined by Duane Stephenson and the iconic Roots Radics. The tour celebrates their new album Reggae Music Never Dies while featuring timeless hits like Same Song and Ball of Fire.
Weekly Events
Mondays
Lei Po’o Making: The Shops of Wailea invites guests to learn how to weave ti leaf leis using ferns and flowers. Lei Po’o can be worn on the head and was typically used as a gift on special occasions by Ali’i (Hawaiian Royalty). This event is open to both keiki and adults and runs from 2:30 to 3:30 pm.
Tuesdays
Polynesian Show at The Shops: This weekly show will highlight Hawaiian hula as well as other dances of Polynesia. The performance will take place at the Shops of Wailea from 5:30 to 6:30 pm.
Coconut Husking at The Shops: From 2:30 to 3:30 pm weekly, the Shops of Wailea will be hosting demonstrations of the traditional and modern methods in husking a coconut. Learn how the Hawaiians would use every part of the coconut from food to crafting eating utensils, jewelry as well as furniture.
Wednesdays
Lei Po’o Making: The Shops of Wailea invites guests to learn how to weave ti leaf leis using ferns and flowers. Lei Po’o can be worn on the head and was typically used as a gift on special occasions by Ali’i (Hawaiian Royalty). This event is open to both keiki and adults and runs from 2:30 to 3:30 pm.
Slack Key Guitar Show: The Masters of Hawaiian Music Slack Key Show is open for live shows once again. The Slack Key Show ohana will perform each week at 6:30 pm at the Napili Kai Beach Resort. Tickets are required for entry, this show is also streamed online.
Thursdays
Coconut Frond Weaving at the Shops: The Shops of Wailea invites guests to try their hand at the highly developed Hawaiian skill of weaving. Coconut frond weaving was used to make baskets, mats, and even toys. This event runs weekly from 4:30 pm to 5:30 pm.
Thursday Night Jams: Come hang at the Plate Lunch Marketplace (you know, the food truck lot across from Costco Gas) and enjoy live music every Thursday night from 6-8 p.m. Don’t forget to pick up an ono smash burger from Haven’s either!
Fridays
Papa Hula at the Shops: Hosted at the Shops of Wailea, Papa Hula is a celebration of the Hawaiian way of life. Enjoy a complimentary dance lesson, complete with costumes and accessories, and the dance movements and their meanings. This interactive performance runs from 4:00 pm to 5:00 pm.
Saturdays
Upcountry Farmers Market: Shop some of the best local souvenirs on the island, indulge in delicious food and support local farmers at one of Maui’s biggest weekly events. Don’t forget to set your morning alarm, as this market favors the early shopper. The Upcountry Farmers Market runs from 7:00 to 11:00 am every Saturday at the Kulamalu Town Center in Pukalani.
Sundays
Maui Gift and Craft Fair: Stop by the Lahaina Gateway Center and browse West Maui’s largest gift and craft fair. This weekly event hosts over 50 vendors, showcasing jewelry, photography, art, crafts, keiki activities, and more. Maui Gift and Craft Fair runs from 9:00 am to 2:00 pm every Sunday.
Maui Sunday Market: Featuring some of Maui’s most renowned food trucks, local vendors, and quality entertainment, the Maui Sunday Market is one of the island’s most popular weekly events. Centrally located at the Kahului Shopping Center, the Maui Sunday Market draws locals and visitors from all corners of the island. The event runs every Sunday from 4:00 pm to 8:00 pm.
For more information or to see the best weekly, monthly, and yearly celebrations, check out our calendar of Upcoming Maui Events.
Mahalo for reading our list of Maui Events May 2025! Have an upcoming event you’d like us to include in the next post? Let us know in the comment section below or contact us directly about how to add your event to our monthly calendar and blog post. Aloha!
Will there be the Maui Jim Shootout the first of June ?