Fall is one of the best times to be on Maui!
The crazy summer crowds slow down. The temperatures dip slightly. And by November, you might even spot some humpback whales!
If you’re planning a trip to Maui in the fall, here are some fun annual events that you can incorporate into your trip planning.
THINGS TO DO ON MAUI IN THE FALL
MAUI EVENTS IN SEPTEMBER
Festivals of Aloha: The Festivals of Aloha celebrates all things Hawaiian through dance, music, fishing, lei-making, food, and more. This Hawaiian cultural showcase runs all autumn with events all around Maui County. This year, the festival kicks off on September 5 with a town party in Wailuku, runs all the way to October with free events all around Maui Nui, from Hana to Molokai. Check out the complete schedule for more info on events.
2025 Dates: September 5 – October 26
Details & Future Dates (as they become available)
St. John’s Kula Festival: This is the biggest and best annual event in Keokea in Upcountry! St. John’s Kula Festival has been around for over four decades. Come enjoy live music, a silent auction, a farmers market, a keiki zone, and a ton of ono local food. It’s a great place to shop and get to know the local Upcountry community. Admission is only $2 and kids under 12 are free.
2025 Date: September 27, 2025.
Details & Future Dates (as they become available)
MAUI EVENTS IN OCTOBER
Maui Fair: GREAT news! The Maui Fair is back after years of not taking place! We’re not sure how this year will differ from past years, but we’re expecting a ton of rides, food, and fun. One of the best parts of the Maui Fair is the food court, so come ready to eat. Besides the rides, you can also check out the 4H and agriculture exhibits, and there’s usually live entertainment, vendors, and art exhibits. We can’t wait!
2025 Dates: October 2-October 5 Wailuku (Central Maui)
Details & Future Dates (as they become available)
Kula Country Farms Pumpkin Patch: Visiting the Kula Pumpkin Patch each October is a treasured tradition for countless Maui families. It’s one of the few places on island where you can have a festive fall experience — despite the endless sunshine and warm weather! This upcountry farm decorates its grounds every year for Halloween, and there are plenty of family photo opportunities. Plus, the bi-coastal views are amazing. If you’re visiting Maui in October with keiki, the Kula Pumpkin Patch is a MUST! Admission is $5, and free for keiki (children) 3 years old or younger.
2025 Dates: October 1-October 31 Kula (Upcountry Maui)
Details & Future Dates (as they become available)
Hawaii Food & Wine Festival: Founded by all-star Hawaii chefs Alan Wong and Roy Yamaguchi, the Hawaii Food and Wine Festival is the biggest (and arguably most iconic) culinary events in Hawaii. The festival takes place every October in locations across the state. The festival’s Maui leg is held in Kaanapali and features a host of awesome culinary events, from wine tastings to dinners prepared by local and international chefs. This year boasts an amazing line-up of chefs, so get your tickets in advance! Stay in the heart of the action at these nearby Kaanapali condos.
2025 Dates: October 13-15, Kaanapali (West Maui)
Details & Future Dates (as they become available)
MAUI EVENTS IN NOVEMBER
Hawaiian Airlines Made in Maui County Festival: The Made in Maui County Festival is the biggest and best product show on Maui! Hundreds of vendors come from all around Maui County (including Hana, Molokai, and Lanai) to sell their Maui County-made goods. You’ll find a range of products here, from jewelry and clothing to plants and art and SO much more. Whether you’re souvenir shopping or finding Christmas gifts for family, this is a great place to look.
2025 Dates: November 7-8, Maui Arts and Cultural Center, Kahului (Central Maui)
Details & Future Dates (as they become available)
MORE TIPS FOR THINGS TO DO ON MAUI IN FALL
Seasonal Whale Watching Cruises on Maui usually begin in mid-November (continuing through mid-May).
Each year, thousands of humpback whales migrate from Alaska to Hawaii. The “official” start of whale season is December 15, but select whale watches start going out around mid-November. Some whales show up as early as September, and you’ll start seeing them here and there near the end of October and into November. Keep your eyes peeled if you’re visiting in fall!
Kihei Fourth Friday Town Parties: Every fourth Friday, Kihei hosts a town party in the Azeka Shopping Center. Come here for ono local food trucks, local vendors, live entertainment, keiki activities, and more!
Free Entertainment: Free entertainment is common at hotels, resorts, and shopping centers around Maui. Centers like Shops of Wailea, Whaler’s Village, and Queen Kaahumanu Center often host free hula shows, ukulele lessons, and cultural activities like lei-making. For other suggestions, check out our list of 25 Free Things To Do on Maui.
Farmers Markets: Support local farmers and vendors at one of Maui’s several amazing farmer’s markets! In addition to vibrant, locally grown produce, most farmers’ markets feature other unique local products like jams and jellies, clothing, jewelry, flowers, and island-themed goodies. Some of our top favorites include the Upcountry Farmers Market, Napili Farmers Market, and South Maui Farmers Market. See our ultimate guide to Maui Farmers Markets.
Live Music on Maui — Mana’o Radio: Live music is still happening around the island, with local musicians jamming almost every night at some of the island’s best restaurants. To find out who’s performing where check out Mana’o Radio’s Music2Nite site for a full lineup of live music on Maui.
Manaʻo Radio (KMNO 91.7 FM) is Maui’s non-commercial all-volunteer radio station. Instead of a canned, pre-programmed song list, you’ll hear local people (volunteer DJs) playing an eclectic selection of the music they love best. Listen while you’re here on Maui, or live stream from their website. Tune in to a truly local radio station! Follow Manaʻo Radio on Facebook for the latest word on their broadcast schedule and live events on Maui.
Grassroots Festivals and Fundraisers: Don’t be shy to buy a ticket and attend local fundraisers, bazaars, and festivals. These events are a great way for visitors to experience an authentic local gathering, and the organizers will love to have you there. There is always plenty of local food (eating is a priority here on Maui!) and entertainment, and often there are fundraising auctions (silent and live) where you can snag great deals on visitor activities like luaus, golf, dining, and boat tours.
Live Webcams: When you are planning your day on Maui, check out these webcams to view current weather conditions around the island. It’s not unusual to be overcast or rainy in one area but clear and sunny just a few minutes away!
Maui Arts & Cultural Center: This is another excellent resource you should check for upcoming events and performances on Maui, from world-famous celebrities and musicians to symphonies and ballet to local Hawaiian cultural programs and festivals. The Maui Arts & Cultural Center (or “the MACC,” as we call it here) is located in Kahului.
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Happy Travels!
Aloha! Tiffany here. I've been blessed to call Maui home since 2011. With a background in the island's finest restaurants and hotels, guiding visitors to create unforgettable Maui memories is more than a skill I've mastered—it's a profound source of joy for me.
