Special Events on Maui

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Maui's newest and most talked-about music event returns to South Maui for its third year, and the 2026 lineup is its strongest yet: Riley Green, Randy Houser, Lukas Nelson, Margo Price, and Liz Rose join host Storme Warren for intimate songwriter-in-the-round sessions across Wailea and Kīhei. The signature 'Songwriters Under the Stars' night lands at the Molokini Garden at Grand Wailea, while the free bar crawl strings together Kīhei's best live-music rooms. Nashville polish, aloha soul.

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The legendary folk-rock trio behind 'A Horse with No Name' and 'Ventura Highway' brings five decades of sun-drenched harmonies to the Castle Theater. A warm, nostalgia-soaked evening with one of the most enduring voices of the 1970s California sound.

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Kumu hula Nāpua Greig and the award-winning Hālau Nā Lei Kaumaka O Uka present their annual hula hōʻike and fundraiser at the Castle Theater. A moving evening of traditional and contemporary hula, oli, and Hawaiian song with guest artists and a silent auction. Mohala Mai means to bloom, and this is island artistry at full flower.

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A voyage, not a race: cancer survivors and supporters paddle six-person outrigger canoes from Lahaina across the ʻAuʻau Channel to Lānaʻi, camp overnight beneath the island's stars, and paddle home, a roughly 36-mile round trip and one of Maui's most moving community traditions. The 17th annual crossing raises critical funds for PCF's free patient programs across Maui County.

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Imua Family Services turns the Maui Arts & Cultural Center into a safe, family-friendly Halloween wonderland for children eight and under. A path of trick-or-treat stations from community partners, a critter encounter zone, and hands-on play areas make this the sweetest, most wholesome way on island to celebrate the holiday.

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Magician David Kuraya brings his acclaimed close-up and stage magic to the intimate ProArts Playhouse in Kīhei for two Sunday evenings. A slick, charming night of sleight of hand that leaves audiences genuinely baffled, in one of Maui's coziest live venues.

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Grammy-nominated musician Henry Kapono curates an evening celebrating the soundtrack of growing up in Hawaiʻi, joined by Jerry Santos, Keola Beamer, and more at the Castle Theater. A heartfelt mix of beloved classics and rising island talent that feels like a warm homecoming. VIP and general seating available at MauiArts.org.

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The Hawaiʻi supergroup of seven artists, including Justin Kawika Young and Shawn Kekoa Pimental, brings a show the MACC bills as"with a dance floor" to the Castle Theater. Expect an unmissable celebration of love, unity, and peace through song on an already stacked island music night.

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The 41st annual Upcountry tradition at St. John's Episcopal Church in Keokea. This beloved community fair features local crafts, live Hawaiian and contemporary music, plant and bake sales, a silent auction, and some of the best malasadas on the island. A quintessential Maui small-town experience.

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Stand-up comedian Morgan Jay brings his Goofy Guy Tour to the Maui Arts & Cultural Center for a single night at the Castle Theater. Known for his high-energy stage presence, improvised musical comedy, and viral social-media following, Jay delivers a show that blends stand-up and song into something entirely his own.

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The celebrated Hawaiian slack-key guitarist and vocalist Justin Kawika Young performs an intimate evening at the Castle Theater. A Na Hoku Hanohano Award winner, Young's music weaves traditional Hawaiian melodies with contemporary acoustic influences, creating a soulful, island-soaked concert experience.

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Hawaii's oldest cultural celebration returns for its 80th year under the theme “Ea Mai Ke Kai Mai – Rise Up from the Sea.” On Maui, the Aloha Festivals weave a Royal Court investiture ceremony, ho'olaule'a street parties, the Makawao Rodeo Weekend, and Hawaiian music and hula performances across the island through late October.

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The 99th Maui County Fair at the War Memorial Special Events Complex in Wailuku. Carnival rides, local food booths, livestock exhibits, and live entertainment. A beloved island tradition that brings together every corner of the community.

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The world premiere of James Nevius's 'Ainakea, a compelling new play presented by Maui OnStage at the Historic 'Iao Theater in Wailuku. This original work explores themes of Hawaiian identity and belonging, with a three-weekend run. An important addition to Maui's arts scene.

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Comedian and actor Matt Fraser brings his stand-up tour to the Castle Theater at the Maui Arts & Cultural Center. Fraser, a headliner known for his sharp storytelling and relatable observational humor, has been selling out venues nationwide. A welcome dose of laughter under the island stars.

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The legendary nine-time Grammy Award-winning band brings their timeless catalog to the Castle Theater at the Maui Arts & Cultural Center. Expect an electrifying night of funk, soul, and R&B from one of the best-selling bands of all time. A bucket-list Maui concert.

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Grammy-winning reggae band SOJA performs live at the Maui Arts & Cultural Center's A&B Amphitheater. The Virginia-bred, globally-minded group brings their signature blend of roots reggae and conscious lyrics for an evening of island-vibe music under the stars.

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The Festivals of Aloha land in East Maui for the beloved Hāna Parade and Hoʻolauleʻa, a week-long celebration that brings together the tight-knit Hāna community and visitors alike. The parade winds through town with horseback riders, paʻu riders, and marching bands, followed by an afternoon of live music, hula, and local food under the Hāna sun. The week also brings a keiki and wahine shoreline fishing tournament on October 18 and a crafters fair.

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The world's premier professional windsurfing competition returns to Hoʻokipa Beach Park on Maui's North Shore. Watch the world's best athletes ride some of the most powerful waves on the planet in this free, family-friendly event. Prime spectating from the bluffs above Hoʻokipa.

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Hawaii's own reggae powerhouse The Green returns to the MACC stage. Known for their lush harmonies and genre-blending sound, the multi-platinum island band delivers a high-energy performance that bridges classic reggae with contemporary Hawaiian music.

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Four Seasons Resort Maui at Wailea hosts an immersive weekend of Hawaiian music, art, and storytelling as part of the statewide Festivals of Aloha. Guests enjoy complimentary cultural activities including lei-making, hula lessons, the Live Aloha Market showcasing island artisans, and the Carmen Hulu Lindsey Leo Ha'iha'i Falsetto Contest.

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The paniolo spirit takes over Upcountry Maui as the Festivals of Aloha celebrate the island’s cowboy heritage in historic Makawao. Expect bronc and barrel racing, roping and ranch-life demonstrations, live music, and plate-lunch lines under the pines. A weekend that honors Maui’s ranching roots with plenty of family fun.

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The legendary Grammy-winning reggae band Steel Pulse performs at the Maui Arts & Cultural Center. With a career spanning five decades, their powerful roots-reggae anthems and electrifying stage presence make this a can't-miss evening for music lovers.

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The island’s premiere Latin and bachata dance event returns to Maui for an evening of music, live performances, and social dancing. Dancers and DJs from across the state converge for a high-energy celebration that has become a fixture on Maui’s cultural calendar. Beginners and seasoned dancers alike are welcome.

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The largest products show in Maui County, featuring more than 140 Maui-made vendors at the Maui Arts & Cultural Center. Artisans, food purveyors, and craft makers showcase what makes Maui's creative economy thrive. Ideal for holiday shopping with a sense of place.

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The 43rd annual Maui Invitational NCAA basketball tournament brings eight top Division I programs to the Lahaina Civic Center. This prestigious early-season tournament is a fixture on Maui's sports calendar, with an electric atmosphere and intense competition.

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Hawaiian Independence Day, known as Lā Kuʻokoʻa, marks the anniversary of the signing of the Anglo-Franco Proclamation recognizing the Kingdom of Hawaiʻi’s sovereignty in 1843. On Maui, the day is observed with cultural ceremonies, hoʻokūpaʻa (protests and celebrations) at key historic sites, and educational events honoring Hawaiian legacy and self-determination.

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Comedian Jo Koy brings his "Koy Meets World" tour to the Maui Arts & Cultural Center's Castle Theater for three nights of stand-up. An intimate theater setting for one of comedy's most bankable headliners.

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A cherished Maui holiday tradition returns to Lahaina's historic Banyan Court. The annual tree lighting features live Hawaiian music, hot chocolate, and the ceremonial lighting of Maui's most iconic banyan tree. A warm, community-centered evening that captures the aloha spirit of the season.

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John Mulaney's "Mister Whatever" tour stops at the Castle Theater for a single night of razor-sharp stand-up. A rare Maui appearance from one of the most celebrated comedians of his generation.

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The comedian, author, and founder of the Butterfly Effect comedy club brings her fast-rising stand-up to the Castle Theater. Summers’ sharp, irreverent observations on family, fame, and the immigrant experience have made her one of the most in-demand comics on the road. A fearless new voice to close out the year.

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Annual marathon along the Ka'anapali coastline. One of Maui's premier sporting events drawing runners from around the world to race through West Maui's most scenic route.

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The Ritz-Carlton Maui, Kapalua hosts its weekly Aloha Friday Market, a vibrant open-air gathering featuring local artisans, live Hawaiian music, and fresh island-grown produce. Browse handcrafted jewelry, traditional woodwork, and locally made art while enjoying the oceanfront setting at the resort’s lobby lawn. A perfect prelude to the weekend.

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One of Maui’s most cherished holiday traditions: Santa Claus arrives not by sleigh but by outrigger canoe, paddling ashore at various beaches across the island. Kāʻanapali Beach, Wailea Beach, and Hāna Bay each host their own landing events, with keiki (children) greeting Santa with Hawaiian songs and leis. Check local resort schedules for exact dates.

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Maui Academy of Performing Arts presents its annual production of The Nutcracker at the Historic ʻIao Theater in Wailuku. This beloved island tradition set to Tchaikovsky’s score features local dancers, vibrant costumes, and a distinctly Hawaiian twist on the classic holiday ballet. Multiple performances throughout December.

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Grand Wailea dresses for the holidays with a nightly tree lighting ceremony, Santa's arrival by outrigger canoe, and the resort's signature Candlelight Concert series, an immersive run of orchestral suites honoring film scores from Hans Zimmer to Coldplay vs. Imagine Dragons inside the Haleakala Ballroom. Festive, polished, and gloriously over the top, it is the definition of a luxury island Christmas.

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Whale Trust's 21st annual celebration of humpback season returns to the Ritz-Carlton Maui, Kapalua for five days of talks with the world's preeminent whale scientists, premieres of breathtaking underwater films, and curated ocean experiences for all ages. Maui is the humpbacks' winter home, and this is the most intimate window into their lives anywhere in the islands.

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Science you can take part in: the Pacific Whale Foundation rallies volunteers along Maui's shorelines to tally humpback sightings in one synchronized afternoon, part of the longest-running whale survey in the islands. Even as a spectator it is a beautiful entry into whale season, and volunteer slots fill quickly each winter.

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Pacific Whale Foundation’s flagship celebration of humpback season returns to Kalama Park in Kihei with live Hawaiian music, hula, a parade, keiki activities, food booths, and whale-science education stations. Exact 2027 dates are announced closer to the season, but mark mid-February and start counting spouts.

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Four-time Grammy winner George Kahumoku Jr. hosts Maui's longest-running live music evening at the open-air Aloha Pavilion of Napili Kai Beach Resort, with Grammy-nominated slack key guitar masters, hula, and storytelling under the stars. An ocean-fringed, moonlit night of true Hawaiian music that belongs on every first-time itinerary; reservations are recommended.

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The traditional Hawaiian season of peace, harvest, and celebration. Cultural events, traditional games, and ceremonies honoring the god Lono take place across Maui. A meaningful time to experience authentic Hawaiian traditions.