The months of October, November, and December are a fantastic time to visit Maui. The islands tend to be a little less crowded this time of year, with the exception of the holidays of course, as the kids go back to school. In addition to quieter beaches and an easier time making restaurant reservations, there are some great fall Maui events that you may want to plan a vacation around. Take a look below at some of the unique autumn happenings on Maui.
Maui Fair (October 1 - 4):
The Maui Fair is one of Maui’s most anticipated annual community events, bringing together residents and visitors for a celebration of local culture, entertainment, food, and family fun. Held at the War Memorial Complex in Wailuku, the fair features exciting carnival rides, live music, agricultural exhibits, local crafts, games, and a wide variety of island-style foods.
Maui Steel Guitar Festival (October 17):
Hawaiian music is made up of some beautiful-sounding string instruments such as the ukulele, slack key guitar, and steel guitar. This free event for the public celebrates the sounds of the steel guitar. It will feature master steel guitar players from across the Hawaiian Islands. Immerse yourself in the sounds of Hawaii and discover new musicians you may not be familiar with.
Hawaii Food & Wine Festival (October 23 – October 25):
This statewide festival has a collection of over one dozen food and wine themed events happening on the various islands in October and early November. On Maui, there is a golf tournament with famous island chef Roy Yamaguchi, an event called “Caviar, Pearls & Aphrodisiacs” which is a grand tasting that explores the world’s most coveted delicacies, and a "No EGGScuses" brunch.
Kula Pumpkin Patch (October 1 – October 31):
Add some color to your vacation condo by picking up a pumpkin at the seasonal pumpkin patch located at Kula Country Farms. Open for the entire month of October, visitors can select their own pumpkin from a variety sizes, colors, and styles. The farm also has fun wooden cutouts and fall decorations that create the perfect backdrop for a family photo. In between your pumpkin hunting, take a minute or two to admire the stunning views of the Maui valley below you. Drinks, snacks, and food will also be served!
Steel Pulse in Concert (October 24):
This legendary British reggae band brings its signature blend of roots reggae, soulful melodies, and powerful messages of unity and social justice to the stage. With decades of influence and a sound that continues to inspire generations, Steel Pulse promises an evening of infectious rhythms, positive energy, and timeless reggae classics. Watch this perform live under the stars at the Maui Arts.
Stomp Out the Hunger 5K (October 31):
This year the 11th annual fun run that raises funds for Hale Kau Kau (food distribution non-profit) is being held on Halloween Day. Costumes are encouraged and even rewarded with grand prizes! Sign up for this community event that includes a 5K race and a one-mile run along the Kihei coastline.
Made in Maui County Festival (November 6 & 7):
Celebrating its 13th year, this two-day festival is the premier shopping event of the year when it comes to finding unique local crafts and goods. Over 9,000 attendees flock to the Maui Arts & Cultural Center where 130+ vendors sell items made on Maui, Molokai or Lanai. Talk directly to vendors and support local businesses. Some of Maui’s favorite food trucks and top musicians will also be in attendance.
Hui Holidays (November 20 – December 24):
Hui No‘eau Visual Arts Center turns its gift shop into an expanded holiday marketplace featuring work from Maui artists and makers, including ceramics, jewelry, textiles, ornaments, home goods and other locally made gifts.
Kula Harvest Festival (November 21):
Upcountry Maui, made up of Makawao, Pukalani, and Kula is paniolo country or cowboy country. Drive past goat farms, cow pastures, and flower fields on your way to the Kula School Harvest Festival. The full day event features live music, pony rides, petting farm, country store, carnival games, and more island-style fun fit for the cooler fall temperatures.
Southwest Maui Invitational (November 23 – 25):
Sports fans and passionate college alumni make the pilgrimage to Maui each November to attend college basketball’s most prestigious early-season tournament. The Southwest Maui Invitational is celebrating its 43rd anniversary in 2026. This year the tournament field of teams includes Arizona, BYU, Colorado State, Clemson, Ole Miss, Providence, VCU, and Washington.