September settles into Maui like a long exhale. The kids are back in school, the visitor crowds thin out just enough to notice, and the island seems to trade its summer hustle for something quieter and more local. It's the kind of month when a Friday night in Kīhei or a Saturday morning in Keokea feels less like an event and more like a homecoming. Here's where to find the aloha this September.
Sunset Tunes ft. Ron Kuala'au
Friday, September 4, 2026 · 6:30–8:00 pm
Kalama Park Bandstand, Kīhei
Maui County's free live music series closes out its short 2026 run with local musician Ron Kuala'au taking the south-end bandstand as the sky over Kīhei fades to pikake pink. Bring your low-back chairs, a blanket, and something cold to sip, and settle in on the lawn while the ocean breeze carries every note. It's the kind of unhurried, kama'āina evening this island does best. Check the 2026 Sunset Tunes schedule.
Maui Jazz & Blues Festival
Sunday, August 31 – Sunday, September 6, 2026 · Main event Sept. 5, 4:30–9:00 pm; Sunday Jazz Brunch Sept. 6, 11 am–2 pm
The Ritz-Carlton Maui, Kapalua
West Maui hums for a full week as the Maui Jazz & Blues Festival returns to Kapalua for its second consecutive year, drawing Grammy winners Steve Turre, Eddie Henderson, Javon Jackson, Joanna Connor and The Iguanas to the resort's oceanfront pavilion. The festival wraps with a Sunday jazz brunch at Ulana Terrace, easy island-style, and organizers are donating more than 200 tickets to Lahaina fire survivors as part of the week's spirit of giving back. Check the Maui Jazz & Blues Festival lineup for the full schedule of shows.
Jewel of the South: A New Orleans Cocktail Takeover
Friday–Saturday, September 4–5, 2026
The Ritz-Carlton Maui, Kapalua
New Orleans' celebrated Jewel of the South, ranked among North America's 50 Best Bars, pops up in Kapalua for a weekend of speakeasy-style craft cocktails, timed perfectly to run alongside the resort's Jazz & Blues Festival lineup. It's a rare taste of the Crescent City set against a Maui sunset. Reserve a spot through the Jewel of the South details before the weekend fills up.
TUMUA — Das' How Tour
Saturday–Sunday, September 5–6, 2026 · 7:30 pm
Maui Arts & Cultural Center, Kahului
Comedy trio TUMUA brings two nights of fast-paced, Pacific Islander sketch and stand-up to the Castle Theater, mixing sharp local humor with the kind of warm, family-rooted storytelling that has audiences laughing and nodding along in the same breath. Grab TUMUA tickets and expect a full house.
Lights for Lahaina — Day of Illumination
- Friday, September 11, 2026 · 4:30–9:00 pm — Our Lahaina Story, Maria Lanakila Catholic Church
- Saturday, September 12, 2026 · 6:00–9:30 pm — Light March, from Puʻunoa Beach to Maria Lanakila Catholic Church
Lahaina town
Two evenings of remembrance and hope unfold in Lahaina as this community gathering continues to honor the town's ongoing healing journey. The first night gathers resource tables, cultural practitioners, keiki hula and live music at Maria Lanakila; the second is a shared, quiet walk through historic Lahaina Town carrying hundreds of lights, ending in kanikapila and ono local food. Shuttles run both evenings from the Lahaina Civic Center, and full Lights for Lahaina event details are worth a look before you plan your evening.
Kapalua Wine & Chef Series ft. Sheldon Simeon
Saturday, September 12, 2026
The Ritz-Carlton Maui, Kapalua
Maui's own James Beard-nominated chef Sheldon Simeon headlines this intimate wine dinner, part of the resort's ongoing series pairing beloved local chefs with premium pours against a Kapalua sunset. It's a night for lingering over every course. Details on the Kapalua Wine & Chef Series are available now.
Perfect Pairings Maui
Friday, September 18, 2026 · 6:00–9:00 pm
Fairmont Kea Lani Hotel, Wailea
Big Brothers Big Sisters Hawai'i's signature Maui fundraiser brings together the island's top chefs with premium wines and spirits for an evening in support of youth mentorship, hosted in the elegant surrounds of the Fairmont Kea Lani. Good food, good cause, good company. Find Perfect Pairings Maui tickets before the event sells out.
Mele for Maui — Hawai'i Symphony Orchestra
Saturday, September 19, 2026 · Mākeke 4:00 pm, concert 6:30–9:00 pm
Royal Lahaina Resort & Bungalows, Kā'anapali
The Hawai'i Symphony Orchestra returns to Maui for the first time in a decade for this free, 64-piece outdoor concert honoring Lahaina's resilience, joined by Amy Hānaiali'i, Raiatea Helm, Keola Beamer, John Cruz, Jeff Peterson and Kalaʻe Camarillo. A local artisan mākeke opens the evening before the orchestra takes the stage under the stars. This is a night worth circling on the calendar — full Mele for Maui event details are online now.
Morgan Jay: Goofy Guy Tour
Friday, September 25, 2026 · 7:00 pm
Maui Arts & Cultural Center, Kahului
Viral comedian and musician Morgan Jay, known for his absurdist song-comedy hybrids, brings his high-energy Goofy Guy Tour to the Castle Theater for a night of genuinely silly, sharply crafted comedy. Come ready to laugh harder than you expect. Grab Morgan Jay tickets while seats remain.
Home in the Islands
Saturday, September 26, 2026 · 7:00 pm
Maui Arts & Cultural Center, Kahului
An evening of contemporary Hawaiian music celebrating the sound and stories of home fills the MACC's intimate McCoy Studio Theater, the kind of night where the music feels close enough to touch. Full Home in the Islands details are available now.
St. John's Kula Festival, 41st annual
Saturday, September 26, 2026 · 9:00 am–4:00 pm
St. John's Episcopal Church, Keokea
Upcountry's biggest tradition returns to Keokea for its 41st year, filling the church grounds with a legendary silent auction, homemade fudge and chow fun, a quilt show, fresh Kula produce and plants, and live entertainment from morning to close. Proceeds support St. John's ministries and each year's partner charities, making this as much a giving-back day as a festival. Plan your visit with the St. John's Kula Festival details — this one draws a crowd.
Justin Kawika Young
Sunday, September 27, 2026 · 5:00 pm
Maui Arts & Cultural Center, Kahului
Local favorite Justin Kawika Young closes out a music-heavy September at the MACC with an evening of Hawaiian and contemporary island sound, the kind of set that sends you home humming. Details and Justin Kawika Young tickets are up now.
Whatever draws you out this September — a symphony under the stars, a wine dinner at sunset, or a slice of fudge in Keokea — Maui's community calendar is full of reasons to gather. We hope to see you out there, kama'āina and visitor alike, celebrating everything that makes this island home.