Things to do on Maui in fall. Halloween pumpkins carved with island designs.

Things To Do On Maui in Fall (September-October-November)

Fall is a truly lovely time on Maui. The hotter weather of summer is behind us as is the busy summer vacation travel period, so the island is less crowded in fall. It’s a great time to visit! Here are some popular things to do on Maui in fall — annual events that you can incorporate into your trip planning.

NOTE: Due to the impacts of COVID-19 on Maui’s tourism, some of the businesses, events, or activities mentioned in this blog may have changed their operations temporarily or permanently. As things change constantly through this transition, please check directly with businesses or event organizers to verify the latest status. Mahalo!




Things to do on Maui in fall: Young hula girl. Aloha Festivals on Maui



Festivals of Aloha: The month-long Festivals of Aloha take place every fall across the state of Hawaii with multiple events that are designed to honor and share Native Hawaiian culture and traditions. Starting in September (and often spilling over into October), you will find a variety of wonderful cultural events taking place in various regions of Maui, as well as on the islands of Lanai and Molokai (which are part of Maui County). Concerts, festivals, parades…all lots of fun! 


Details & Future Dates (as they become available)






Things to do on Maui in fall: Annual ukulele festival on the lawn at Maui Arts & Cultural Center





Maui Ukulele Festival: This annual event occurs in the lovely open-air courtyard of the Maui Arts & Cultural Center in Kahului. Bring a lawn chair, beach mat, or blanket, and relax on the lawn for an afternoon of happy ukulele jamming!

2020 Date: September 27 Maui Arts & Cultural Center, Kahului (Central Maui) THIS EVENT WILL LIKELY BE CANCELLED DUE TO COVID-19 PANDEMIC

Details & Future Dates (as they become available)







Things to do on Maui in fall: shave ice

Maui County Fair: Each year in the fall (September or October), the annual Maui County Fair kicks off on a Thursday afternoon with a parade and continues through Sunday with carnival rides, food, exhibits, entertainment, and fun competitions like the annual Maui Fire Department chili cook off. Taking place at the War Memorial Complex in Wailuku, the County Fair is a great community event for both visitors and locals to enjoy! Stay in Maalaea — just 15 minutes away.

2020 Date: 98th Annual Maui Fair was scheduled for October 1-4  War Memorial Complex, Wailuku (Central Maui) CANCELLED DUE TO COVID-19 PANDEMIC

Details & Future Dates (as they become available)





Things to do on Maui in fall: Marathon runner
Copyright Polinahe Photography


Maui Marathon: The Annual Maui Marathon, a Boston Marathon qualifier event, follows a 26.2-mile course across the island from Kahului to Kaanapali and is considered one of the 10 most scenic marathons in the U.S. If you are on Maui that day and aren’t running in the marathon, you can still join in the fun by cheering on the participants along the route. Stay in Kaanapali at one of these hotels/resorts!

2020 Date:  50th Annual Maui Marathon, usually scheduled for fall, has been postponed to April 25, 2021 due to the COVID-19 pandemic (Ends in Kaanapali, West Maui)

Details & Future Dates (as they become available)








Things to do on Maui in fall: people drinking wineHawaii Food & Wine Festival: This statewide event takes place over three weeks on multiple islands, showcasing Hawaii’s locally grown foods and featuring a roster of internationally known master chefs and culinary personalities. Don’t miss the Hawaii Food & Wine Festival events taking place on Maui each year in the Kaanapali Beach Resort area! Stay nearby at these Kaanapali condos.

2020 Dates: October 16-17  Kaanapali (West Maui) THIS EVENT MAY BE CANCELLED DUE TO COVID-19 PANDEMIC

Details & Future Dates (as they become available)








XTERRA World Championships: The world’s premier off-road triathlon, combining a 1.5 kilometer (1 mile) rough water swim, a 32-kilometer (20 mile) mountain bike race climbing 3,500 feet up the West Maui Mountains, and a 10.5-kilometer (6.5 mile) trail run. Whew! This event draws around 800 athletes from 28 countries including professionals and amateurs. Places to stay in Kapalua.

2020 Date: CANCELLED DUE TO COVID-19 PANDEMIC. The next event date is October 31, 2021. Based at Ritz-Carlton Kapalua (West Maui)

Details & Future Dates (as they become available)




Things to do on Maui in fall: Halloween parade in Lahaina
Copyright Polinahe Photography




Halloween in Lahaina: Dubbed the Mardi Gras of the Pacific, the annual Halloween celebration in Lahaina draws around 25,000 people each year! The celebration starts in late afternoon with a kid-friendly activity—the Keiki (“children”) Halloween Costume Parade—which is completely adorable. The festivities continue until midnight with live music, an adult costume contest (with incredibly elaborate costumes!) and lots more fun. (The later the hour, the more adult-oriented the crowd and the costumes become, so be forewarned if you are traveling with children.) Stay in a Lahaina condo or B&B!

2020 Date: October 31 Front Street, Lahaina (West Maui) THIS EVENT MAY BE CANCELLED DUE TO COVID-19 PANDEMIC

Details (as they become available)





Things to do on Maui in fall: Colorful island-print dishtowels
Copyright Polinahe Photography



“Made in Maui County” Festival: If you are looking for unique locally made products, this is the event for you! This new annual festival has quickly become Maui’s largest venue for local vendors and craftsmen to show their products: food, produce and plants, arts and crafts, jewelry, fashion, gifts, collectibles. A great place to find unusual, one-of-a-kind local products for yourself or for gifts to take home to friends and family. And just in time for Christmas!

2020 Dates: November 6-7  Maui Arts & Cultural Center, Kahului (Central Maui) THIS EVENT MAY BE CANCELLED DUE TO COVID-19 PANDEMIC

Details & Future Dates (as they become available)





Restaurant Week WaileaFoodie alert! November means it’s time once again for Restaurant Week Wailea. Twice a year, in spring and fall, Wailea’s fabulous, world-renowned restaurants celebrate Restaurant Week Wailea with three course, pre-fixe menus for just $29, $39, $49 or $59 per person. This is a wonderful opportunity to experience these acclaimed restaurants at a great value and support a worthwhile cause while you’re munching — a portion of the proceeds is donated to the Maui Food Bank. Stay at these Wailea area resorts or condos


Details & Future Dates (as they become available)





Seasonal Whale Watching Cruises on Maui usually begin in mid-November (continuing through mid-May). 

Last Chance for Parasailing! This activity does not take place in Maui waters from December 15 to May 15 each year due to the presence of the humpback whales. So a fall visit is perfect for parasailing.

Things to do on Maui in fall: Maui Town Party sign on Front Street in LahainaFriday Night Town Parties: If it’s Friday, there’s a party on Maui! The Town Parties (sponsored by Maui County) take place on Friday evenings in different towns across the island. The town parties are great fun for both visitors and residents, with local food, entertainment, and vendors. More Details.

• First Friday of the month — Wailuku Town Party (Central Maui) 

• Second Friday — Lahaina Town Party (West Maui)

• Third Friday — Makawao Town Party (Upcountry); this one takes place every other month, rather than monthly

• Fourth Friday – Kihei Town Party (South Maui)


Free Entertainment: When you are here, make sure you check for entertainment and events at nearby hotels and resorts, as well as island shopping centers, which often offer free hula shows, activities like lei making and ukulele lessons, and live Hawaiian entertainment. And check out my list of 25 Free Things To Do on Maui for other suggestions.

Mana’o Radio: Tune in to a truly local radio station! Mana’o 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. The first Sunday of every month, enjoy a great lineup of live local entertainment from 2 to 5 p.m. at Casanova Italian Restaurant in Makawao (upcountry Maui). $10 donation at the door is a fundraiser for Mana’o Radio.

Grassroots Festivals and Fundraisers: Don’t be shy to buy a ticket and attend local school, church, and charity 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 boat tours, golf, dining, and helicopter rides.

The Maui News: The “Maui Scene” section in the Thursday issue of the daily Maui News is a great resource for what’s happening on the island each week, as well as current special offers from activities and restaurants. Pick up a copy of the Thursday Maui News when you’re here!

Live Webcams: When you are here planning your day on Maui, check out these webcams to view current weather conditions around the island. It’s not unusual for it 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.

Things to do on Maui in fall: Courtyard pavilion at the Maui Arts & Cultural Center


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Happy Travels!

Candy Aluli, Publisher

Questions? Comments? Drop me a line:

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