09-30-2025
Maui Events in October
Events & Festivals on the island of Maui
President & certified Hawaii travel expert with 15+ years of experience in Hawaii tourism.
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Maui in October feels like one of its best-kept secrets: still warm and bright, with fewer crowds, and a richer chance to slow down and live like a local. The valley towns, resort areas, UPcountry regions, and the North Shore host festivals that highlight food, art, culture, and natural beauty. Plus, October is a prime time for certain ocean sports and wind-related events.
2025 Events and Festivities
Annual Hawaii Food and Wine Festival
One of the most anticipated culinary events in the Pacific, the Hawaii Food and Wine Festival brings together a star-studded lineup of world-renowned chefs, winemakers, and mixologists for an unforgettable weekend. Set against the stunning backdrop of Kaanapali, this festival is a paradise for food enthusiasts. Attendees can indulge in gourmet dishes crafted with fresh, local ingredients, savor premium wines, and enjoy creative cocktails crafted by top mixologists. With exclusive tasting menus, cooking demonstrations, and interactive culinary experiences, this festival is a true feast for the senses.
When: October 24th-26th
Where: Kaanapali, Maui Venues
More Info: Food & Wine Festival
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Maui County Fair
The Maui County Fair is a time-honored tradition that brings the local community together for a weekend of fun, entertainment, and family-friendly activities. Held at the War Memorial Complex in Wailuku, the fair offers a variety of attractions, including thrilling carnival rides, game booths, live entertainment, and delicious local food. Special events, such as the chili cook-off and pie contest, add a touch of friendly competition, while the grand parade kicks off the festivities with vibrant floats and performances. For nearly a century, this fair has been a cherished event for both locals and visitors, offering a glimpse into the heart of Maui’s community spirit.
When: October 2nd-October 5th
Where: War Memorial Complex, Wailuku
More Info: Maui County Fair
Aloha Classic
What to Expect: Elite windsurfing competition in big wave conditions, often regarded as a culminating event for wave surfers.
Why Go: For action, athleticism, spectacle, and seeing Maui’s ocean in high gear.
When: October 13th-24th
Where: Ho‘okipa Beach Park, North Shore, Maui
More Info: Aloha Classic
October on Maui offers a smooth balance: fun for families and locals via the County Fair, windsurfing excitement at Aloha Classic, and culinary indulgence with the Food & Wine Festival.
If your stay covers late October, aligning with the Maui Food & Wine events is a treat. And if you're into windsurfing or watching pro wave riders, Ho‘okipa is a must. For more relaxed days, the festivals and fairs offer excellent snapshots of local life.
Published by: Tori C. Derrick
President & certified Hawaii travel expert with 15+ years of experience in Hawaii tourism.
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