Maui Events September 2025

What’s Happening on Maui for September 2025?

Summer is coming to an end on Maui — but the fun isn’t! September usually marks the start of Maui’s slow season. Kids go back to school and the island becomes quieter. It’s one of the best times to visit Maui on a budget or to avoid the crowds. We’ve got a ton of fun events happening this September, from magic shows to hula festivals and more!

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 September 2025

September 4 

Country Night: Get ready to two-step, swing, and stomp at Country Night at Da Playground. Whether you’re a tried-and-true paniolo or city slicker, everyone is welcome, ya’ll. Learn to line dance and listen to your favorite country tunes. 21+, 6:00 pm. 

September 5

Wailuku First Friday: This monthly street party features live music, vendors, food, and community spirit. Don’t miss it on Market Street from 6 pm to 9 pm. 

DJ Noiz and Kennyon Brown: With a discography full of feel-good island hits like “Come My Way” and “Island Girl,” DJ Noiz and Kennyon Brown are bringing their high-energy beats and melodies to Da Playground. Get your tickets in advance! 21+, 8:00 pm. 

September 6

Al Di Meola Electric Band: Al Di Meola, one of the most influential guitarists of all time, has spent over five decades blending intricate rhythms and lyrical melodies into award-winning, genre-defying works—earning Grammy and international honors, millions of album sales, and lasting acclaim. Don’t miss this special Maui performance! Maui Arts and Cultural Center, 7:30 pm.

Led Zepplica: Led Zepplica is an internationally acclaimed Led Zeppelin tribute band—and they’re bringing their thunder to Da Playground for a night of old-school rock and roll. 21+, 8:00 pm. 

La Ulu Festival: Celebrate ulu (breadfruit)—a Polynesian staple—at La Ulu Fest! Enjoy live music, cultural activities, and lots of ulu treats! Maui Nui Botanical Gardens, 9:00 am – 2:00 pm. 

September 7

10th Annual Sophie Swim: Join the 1.25 mile open water swim race from Kahekili Beach Park to Puu Kekaa (Black Rock) and back. Rave by age and division with or without fins. Money raised will go to the Sophia DeLoria Foundation Fund. 

White Hawaiian: Broadway’s Eric Gilliom’s hilarious one-man musical extravaganza is back at Pro Arts Playhouse! This show traces Hawaii’s unique history and Eric’s life growing up in Hawaii. White Hawaiian runs every Sunday in September at Pro Arts Playhouse. 

Kula Hospital Hoolaulea: Head to beautiful Keokea for a day of community, live music, food, and vendors and celebrate Kula Hospital’s 115th anniversary! Kula Hospital, 10:00 am to 2:00 pm. 

September 11

Comedian Kitty Pineapple: The hilarious and wildly entertaining comedian Kitty Pineapple returns to Da Playground for a night of laughs. Known for her quick wit and bold humor, Kitty brings the kind of comedy that keeps you laughing after the show ends. 21+, 6:00 pm.

18th Annual Ku Mai Ka Hula: Maui’s only adult hula competition! This year’s competition features award-winning halau from around Hawaii, Japan, and the continental US. Two day event. Maui Arts and Cultural Center. 

September 12 

Kanekoa: Maui’s favorite jam band is back for another epic show. These ukulele masters hit the stage with Hawaiian roots and high energy, creating a sound they call Hawaiian jam rock. Don’t miss this Na Hoku Hanohano Award winning band. Pro Arts Playhouse, 7:30 pm. 

Retro Rewind: Take it back in time at this 70s, 80s, and 90s dance party! Come dressed in your best vintage and be ready to bust a move to three decades of music. 21+, da Playground, 9:00 pm.

Aloha Friday: Enjoy an evening of Hawaiian cultural exhibits, hands-on activities, Hawaiian music, and hula. Listen to the sweet sounds of Kalama School Ukulele Band while enjoying some shopping and food and drink! Queen Kaahumanu Center, 5:00 pm – 8:00 pm. 

September 17

Sammy Obeid: Sammy Obeid turned down a job at Google to be a comedian. Now the host of 100 Humans on Netflix, he’s also appeared on NBC’s Last Comic Standing and America’s Got Talent, and is best known for his world record of performing comedy 1,001 nights in a row. Don’t miss him at the Pro Arts Playhouse. 7:00 pm. 

September 19 

Magic in Paradise: Prepare to be dazzled by world-class entertainer and expert in sleight-of-hand magic, Maui’s own David Kuraya. David performed regularly at Warren and Annabelle’s Magic Nightclub in Lahaina before the fires. At each show, he donates part of his proceeds to local charities. Pro Arts Playhouse, 7:30 pm. 

Decades Party: Take it back to the decade of flip phones, low-rise jeans, and hit music. Dance to all your favorite 2000s anthems and dress in your best 2000s gear. Get ready to party like its 2005. 21+, da Playground, 9:00 pm. 

September 20

Richard Ho‘opi‘i Leo Ki‘eki‘e Falsetto Contest: This annual Hawaiian falsetto contest provides a championship opportunity for amateur falsetto singers and provides a platform for the preservation and perpetuation of Hawaii’s unique falsetto traditions – held annually at the Ritz Carlton Kapalua Resort as part of the Festivals of Aloha. 

September 27 

St. John’s Kula Festival: The 40th annual St. John’s Kula Festival is the biggest day of the year in the small town of Keokea. This popular Maui-style festival features live entertainment, food vendors, a silent auction, bake sale, Maui Quilt Guild display, keiki zone and much more. Entry is just $2 and free for kids under 10. St. John’s Episcopal Church, 9 am to 4 pm. 

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

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.

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.

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.

Thursdays

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, the Shops of Wailea will be hosting a demonstration 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.

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.

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 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.

Time will tell what happens this month!

For more information or to see the best weekly, monthly, and yearly celebrations, check out our calendar of Upcoming Maui Events.