Just as the chill of October starts to sweep in, pack your shorts, flip-flops, and sunscreen. Maui fall vacation, here you come!
Just because it’s an off season doesn’t mean there isn’t still plenty to do in Maui during October. Here are some great events that will give you a chance to rub elbows with the locals.
October 1-31, 2025
Kula Country Farms Pumpkin Patch
(Kula, Maui) – A month-long, family-friendly fall tradition where visitors pick their own pumpkins, enjoy a children’s garden, farm animals, a sunflower patch and more. If you’re just visiting Maui, and don’t want a pumpkin, it’s still worth visiting (especially with kids.) There’s food, shopping, and amazing photo opportunities.
The patch is open daily throughout October ( 9am–3:454pm.)
October 2-5 2025
98th Maui County Fair
(Wailuku) – Maui’s largest community fair, featuring carnival rides, local food booths, live entertainment, and a parade.The fair is being held at War Memorial Complex. It’s fun for the whole family, but be prepared to spend a lot more than you might at a mainland fairground. Rides are short and costly.
The fair is usually held for 4 days: 5pm-11pm Thursday and Friday, 10am-midnight Saturday, and 10am-11pm on Sunday.
October 4-5, 2025
16th Annual Paddle for Life
(Lahaina → Lāna‘i) – A large-scale outrigger canoe event organized by the Pacific Cancer Foundation, teams of cancer survivors and supporters paddle 18 miles each way across the ʻAuʻau Channel (36-mile roundtrip) from Maui to Lānaʻi and back, raising funds for cancer care.
If you want to participate in paddling, you’ll want to register soon! You’ll build your own page and begin fundraising from your own ‘ohana.
October 18-25, 2025
Festivals of Aloha
(Molokai, Hana, Wailea, Makawao) – Each fall, the Festivals of Aloha bring Hawaiian culture to life across Maui Nui. In October 2025, celebrations include the Moloka‘i Ho‘olaule‘a and a full week of cultural events in Hāna (Oct 18-25). Expect hula competitions, Hawaiian music concerts, crafts, food, and parades that honor traditions while welcoming the community and visitors to join in.
There are even events at the Four Seasons Wailea and in Makawao (Oskie Rice Memorial Rodeo.)
October 20-26, 2025
Maui Jazz & Blues Festival
(Kapalua) – From October 20-26, 2025, the Ritz-Carlton Kapalua will host the 10th annual Maui Jazz & Blues Festival. This week-long event attracts Grammy-winning musicians from Hawaiʻi and around the world, with intimate resort performances leading up to a major outdoor concert. It’s a chance to experience world-class jazz and blues in a breathtaking oceanfront setting.
Tickets go on sale August 22nd.
October 24-26, 2025
15th Hawai‘i Food & Wine Festival
(Kaʻanapali) Maui’s culinary highlight of the year happens October 24-26, 2025, when the Hawai‘i Food & Wine Festival takes over Kaʻanapali. Celebrity chefs, winemakers, and mixologists collaborate on lavish dinners, tastings, and cooking demonstrations that spotlight Hawaiʻi’s homegrown ingredients. It’s a premier food and wine experience with a strong local farm-to-table focus, across Big Island, Oahu, and Maui.
Maui Arts & Cultural Center (MACC)
(Kahului) – October 2025 at the MACC features a diverse lineup: comedian Brad Williams (Oct 8), island reggae favorite Kolohe Kai (Oct 10), Tumua’s comedy tour (Oct 24–25), and the beloved Maui ‘Ukulele Festival wrapping up the month (Oct 26). The MACC continues to serve as Maui’s hub for big-name concerts, comedy, and cultural showcases, drawing both locals and visitors.
Note, Maui is a very relaxed place, and certain event schedules may change. Remember, you’re on vacation. Relax. Take everything in stride! If an event gets canceled, you can always go to the beach!
To learn how you can stay in a gorgeous, spacious vacation condo in South Maui for a surprisingly reasonable price, contact Ali’i Resorts today 808-879-6284.
