Maui Events May 2024


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!

maui event calendar

What’s Happening on Maui for May 2024?

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 2024

May 1 


Lei Day Heritage Festival: 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. (This event has yet to be locked in for 2024, but it takes place every year, so we have a good feeling it will happen this year, too!)

Lei Po'o Making

May 3 

A Tribute to 90s R&B: Get ready to transport back in time to the golden era of R&B at da Playground, featuring the dynamic duo of Tanama Colibri and the eclectic sounds of Suede. Your ticket also includes admission to the POP! That After Party, where the festivities continue with beats by Joe Cortez and DJ LX. 7:30 pm, 21+. 

May 4 

Led Zepplica the Led Zeppelin Experience: What’s the next best thing to seeing Led Zeppelin live in the 1970s? Seeing Led Zepplica at da Playground Maui! This Zeppelin tribute band has been performing since1989, and has a reputation for being the best Led Zeppelin tribute band in the United States. 8 pm, 21+.

Junie B Jones the Musical JR: Maui OnStage presents a musical adaptation of Barbara Park’s best-selling children’s novel, Junie B Jones. You and your keiki won’t want to miss this at the historic Iao Theater, May 4-12. 

May 5 

James Taylor: Music legend James Taylor returns to Maui with his all-star band for a special concert outdoors under the stars. His songs have had a profound influence on music lovers from all walks of life, from Fire and Rain to Sweet Baby James and many more. Don’t miss him at the Maui Arts and Cultural Center. 5 pm

May 10 

The Mayjah Rayjah Music Festival: Night one of the Mayjah Rayjah Music Festival kicks off with SUBLIME with Rome, featuring special guests Likkle Jordie and Ten Feet. Gates open at 5:00 pm. Maui Arts and Cultural Center.


May 11


48th Annual Seabury Hall Craft Fair: This family-friendly event takes place on the beautiful Seabury Hall Campus in Upcountry Maui and is packed with fun activities for all ages. You’ll find talented crafters, a Keiki zone for the kids, live entertainment, delicious food booths, and more. Plus, it’s always the day before Mother’s Day, so you can get a jumpstart on your celebrations (and sneakily grab some presents behind mom’s back). The fair starts at 9am and goes until 3pm, and admission is $10 for adults and free for kids 12 and under. A $20 premium parking option is available. For more info, head to

The Mayjah Rayjah Music Festival: Night two of the Mayjah Rayjah Music Festival features one of the biggest bands in reggae today: SOJA. Also joining them will be special guests Kaikena Scanlan and Malino. Gates open at 5:00 pm. Maui Arts and Cultural Center.

Seabury Hall Craft Fair Event


May 17 

Artist 2 Artist – Henry Kapono and Jerry Santos: Multiple award-winning artist Henry Kapono is back to share the stage with some of Hawaii’s most diverse, talented, and iconic musical legends. This time he’ll be joined by Jerry Santos of Olomanu and Josh Kahula of NuffSedd. Henry will “jam” and “talk story” one-on-one with each artist, allowing the audience to get to know the people behind the music. 

42nd Maui Classical Music Festival: The 42nd Maui Classical Music Festival kicks off at Makawao Union Church on May 17 and tours venues around Maui until May 26, culminating with two nights at the historic Iao Theater. If you love classical music, mark your calendars.

May 18 

Maui Brewer’s Fest: Beer lovers, rejoice! The coveted Maui Brewer’s Fest returns to the Maui Arts and Cultural Center after a three year hiatus. Your general admission ticket gets you 8 (4oz) beer tastings, selections from a variety of food vendors, and all-day live entertainment. This year, over two dozen breweries from around Hawaii and the United States are coming to the MACC to share their inventive brews. Get your tickets in advance!

Maui Events Brewers Festival


May 19 


Justin Kawika Young: Hailing from Hawaii, Justin Kawika Young’s musical journey is a testament to the power of talent and perseverance. Young boasts an impressive 11 number-one hits on Hawaii radio and collaborations with singer-songwriter Colbie Calliat. Don’t miss him at da Playground! 8 pm, 21+.


May 23 


Can’t Even: Can’t Even is a national touring comedy company with a lineup of comics from Austin, Los Angeles, Chicago, and beyond. This comedic showcase includes riotous acts from Caitlin Benson and Uncle Lazer, as well as special guests, Chino LaForge of Maui and Jesse Mumma of Hawaii Island. 


May 24 


Rex Navarette: Rex Navarrete is one of the hardest working, relatively unknown American comedians today, despite performing alongside notable names like Robin Williams, George Lopez, Ali Wong, and more. You may have seen him on “Lopez Tonight,” “Live at Gotham,” or “MTV Philippines.” Catch him at the Maui Arts and Cultural Center!

Weekly Events


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.


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.


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.


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! 

Thursday night jams with Tj Favella


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.


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.

Pukalani Farmers Market


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.

maui top things to do 2019

Mahalo for reading our list of Maui Events May 2024! 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!

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