October on Maui opens with the smell of fair food drifting over Wailuku and closes with keiki in costume on the MACC lawn. In between, the island fills with hula, rodeo, world-class windsurfing at Hoʻokipa, and Festivals of Aloha gatherings stretching from Lānaʻi to Hāna. Here's what's happening this month.
99th Maui County Fair
Thursday, October 1 – Sunday, October 4
War Memorial Special Events Complex, Wailuku
The fair is back for its 99th year, and it remains one of the few weekends when the whole island seems to show up in one place. Expect rides, ʻono food booths, live music, and livestock and horticulture exhibits, plus contests that pull in everyone from keiki to kūpuna. Before you head over, check the Maui County Fair site for entry details: clear bags are required, and reusable water bottles need to be empty at the gate. Go early in the evening, grab something fried, and settle in for a night under the lights.
Kula Country Farms Pumpkin Patch
Open through the month of October
Kula Country Farms, 6240 Kula Highway, Kula
Upcountry has its own version of fall, and it lives at the family-run Kula Country Farms. The pumpkin patch is open all month, with a children's garden, farm animals, and a sunflower patch set against sweeping views down to the ocean. Keiki can hunt for the perfect pumpkin while parents take in the view from the slopes of Haleakalā. Weekdays tend to be quieter if you'd rather skip the weekend crowds.
ʻAinakea at the Historic ʻĪao Theater
October 2–18 · Fridays 7:30 p.m., Saturdays and Sundays 3 p.m.
Historic ʻĪao Theater, Wailuku
A new Maui story takes the stage in the island's oldest theater. ʻAinakea, a world premiere by Maui playwright James Nevius and directed by Francis Tauʻa, is set on the west side in 1953. It follows a family and their failing sugar plantation, adapted from Chekhov. Tickets through Maui OnStage run $10–$45, so this is an easy way to support local theater and a local playwright in one evening.
Kapalua Concert Series featuring HAPA
Friday, October 2 · 6–9 p.m.
Alaloa Lounge, The Ritz-Carlton Maui, Kapalua
Few sounds say Maui like HAPA, and hearing the award-winning duo in the Alaloa Lounge as evening settles over Kapalua is a real treat. The Kapalua Concert Series is first-come seating with no reservations, so arrive early for a good spot. Food and drink are available for purchase and valet is complimentary, with full details on the HAPA concert page. It makes an easy pau hana plan for West Side ʻohana and friends.
Festivals of Aloha
Saturday, October 3 – Sunday, October 25
- Sat, Oct. 3 — Lānaʻi: Lānaʻi Hoʻolauleʻa at Four Seasons Resort Lānaʻi, 10 a.m.–5 p.m.
- Fri, Oct. 9 — Molokaʻi: Molokaʻi Hoʻolauleʻa at the Community Health Center, 5:30–9:30 p.m.
- Oct. 17–24 — Hāna: Hāna Parade and Hoʻolauleʻa at Hāna Ballpark Oct. 17 (11 a.m.), then a week of craft fairs at Helene Hall, a floral lei contest and Hawaiiana Night Oct. 22, and Hōʻike Night Oct. 24
- Fri, Oct. 23 — Makawao: Oskie Rice Arena during Rodeo Weekend
- Oct. 23–25 — Wailea: Four Seasons Resort Maui — Carmen Hulu Lindsey Leo Haʻihaʻi Falsetto Contest (Fri, doors 5:30 p.m.), Hula Is the Heartbeat (Sat, 6 p.m.), and Sounds of the Sea with Kūikawā (Sun, 7 p.m.), plus a daytime Live Aloha Market and cultural practitioners; off-site parking with free shuttle
This year's theme, Ea Mai Ke Kai Mai (Rise Up from the Sea), carries Hawaiian music, hula, cultural demonstrations, local food, and artisans across Maui County all month long. Each gathering takes on the character of its community. Lānaʻi and Molokaʻi host intimate island celebrations, and Hāna fills a whole week with parades, contests, and Hōʻike Night. In Wailea, three evenings bring leo haʻihaʻi falsetto, hula, and oceanside mele. The full Festivals of Aloha 2026 schedule has every detail, so pick a stop, or two, and go share in the pilina.
Matt Fraser
Wednesday, October 7 · 7:30 p.m.
Maui Arts & Cultural Center, Kahului
Psychic medium Matt Fraser brings his live show to Kahului for one night. Fans of his television work know the format: audience readings, personal stories, and plenty of emotional moments along the way. Tickets are available through Matt Fraser at the MACC. Go with a friend and plan on talking about it the whole drive home.
Reggae month at the MACC: SOJA, The Green, and Steel Pulse
October 9, 23, and 24
- Friday, Oct. 9 — SOJA, 7 p.m.
- Friday, Oct. 23 — The Green, 7 p.m.
- Saturday, Oct. 24 — Steel Pulse, 6 p.m.
Reggae fans, clear your calendars. Three headliners land at the MACC this month, starting with SOJA and building to back-to-back nights with Hawaiʻi's own The Green and UK roots legends Steel Pulse. The Green have long been a fixture of island reggae, and Steel Pulse carry decades of roots history onto the stage. Check the MACC events calendar for tickets, and consider making a full weekend of the final two nights.
The Toxic Avenger (the musical)
October 16–31 · Thurs–Sat 7:30 p.m., Sundays 2 p.m., Halloween 4 and 8 p.m.
ProArts Playhouse, Kīhei
For a Halloween season with a sense of humor, ProArts has you covered. This Outer Critics Circle Award-winning rock musical is campy, loud, and gleefully over the top, and it runs right through Halloween night with two shows on the 31st. Tickets for The Toxic Avenger at ProArts range from $26.50 to $47.70. The Kīhei playhouse is intimate enough that every seat feels close to the action.
Mōhala Mai: A 30th Anniversary Celebration
Saturday, October 17 · 7 p.m.
Castle Theater, Maui Arts & Cultural Center, Kahului
Hālau Nā Lei Kaumaka o Uka began in a garage in Upcountry Maui and went on to become a Merrie Monarch overall champion. Under Kumu Hula Nāpua Silva, the hālau marks 30 years with more than 200 dancers from Maui, Japan, and Mexico, honoring three decades of hula and mele along with the next generation who will carry them forward. Tickets for Mōhala Mai 2026 are $50, $55, and $65. Bring non-perishable items for the Maui Food Bank.
Aloha Classic
October 19–30 (waiting period) · opening blessing Monday, Oct. 19, 9 a.m.
Hoʻokipa Beach Park, near Pāʻia
The world's best return to Hoʻokipa for the Aloha Classic, a PWA 5-star stop on the world tour. The event runs on a waiting period, so heats go only on days with enough wind and swell. It pays to check conditions before heading out the Hāna Highway. When it's on, the cliffside lookout above the reef is free and puts you close to the action. The opening blessing on October 19 sets the tone for the whole contest.
Oskie Rice Memorial Rodeo
Friday, October 23 – Sunday, October 25
- Fri, Oct. 23 — Bull Bash, 6 p.m.
- Sat, Oct. 24 — Saturday Night Rodeo, 6 p.m.
- Sun, Oct. 25 — Championship Rodeo, 1 p.m.
Makawao's paniolo roots come to life at the Oskie Rice Event Center on Olinda Road. The weekend opens with a Friday night Bull Bash and builds to Sunday's Championship Rodeo, when competitors ride for buckles. It also overlaps with Festivals of Aloha in Makawao, so you can pair rodeo action with music and hula at the arena. Tickets for the Oskie Rice Memorial Rodeo are on sale now.
Hawaiʻi Food & Wine Festival: Kāʻanapali
Friday, October 23 – Sunday, October 25
- Fri, Oct. 23 — 28th Annual Roy Yamaguchi Golf Classic, Kāʻanapali Golf Course and Roy's Kāʻanapali
- Sat, Oct. 24 — Caviar, Pearls & Aphrodisiacs, Sheraton Maui, 6–9 p.m.
- Sun, Oct. 25 — No EGGScuses, Let's Brunch!, Royal Lahaina Resort, 11 a.m.–1 p.m.
Maui's weekend of the statewide Hawaiʻi Food & Wine Festival settles into Kāʻanapali with three ticketed events. They bring together chefs, winemakers, and the local farmers and fishermen whose work fills the plate. Saturday night at the Sheraton is the headline, and Sunday brunch at Royal Lahaina offers a slower way to close the weekend. Tickets are already on sale, so book early if one of these is on your list.
Broadway on Maui: A Night at the Masquerade
Saturday, October 24 · 7 p.m.
Historic ʻĪao Theater, Wailuku
Tony Award winner Lauren Patten, star of Jagged Little Pill, headlines a Broadway on Maui concert at the ʻĪao Theater alongside some of the island's finest singers. It's a rare chance to hear Broadway-caliber vocals in a nearly century-old Wailuku landmark, with a touch of masquerade flair. Tickets through Maui OnStage run $25–$55, with $10 off for kūpuna and students.
Imua Family Services Keiki Halloween Festival and Starry Night Cinema
Friday, October 30 · gates 5 p.m.
A&B Amphitheater, Maui Arts & Cultural Center, Kahului
This free evening has become a highlight of the season for Maui families. Keiki can make their way through dozens of trick-or-treat stations hosted by nonprofits and local businesses, meet some friendly critters, and enjoy live music and food trucks. As the sun goes down, spread a blanket on the lawn for an outdoor screening of Monsters, Inc. The Keiki Halloween Festival doesn't allow coolers or outside food, so come hungry and support the vendors.
From fair nights in Wailuku to hula in Wailea and bull riding in Makawao, October gives every corner of the island a reason to gather. Pick a few, bring your ʻohana, and enjoy the season on Maui.