Upcountry Winter Fest brings seasonal magic to Upcountry Maui

The Upcountry Winter Fest presented by the Kekaulike High School Foundation is returning this year, bringing a sparkling array of winter activities, live entertainment, and seasonal delights to Upcountry, Maui.

“Whether you’re a holiday enthusiast or simply looking to embrace the cozy charm of the season, the Upcountry Winter Fest promises to be a magical event for all ages,” organizers said.

Taking place on Saturday, Nov. 29, 2025 from 3 to 8 p.m., this year’s festival will transform the King Kekaulike High School campus into a winter wonderland, offering a festive atmosphere, family-friendly activities, and plenty of opportunities to make memories with friends and loved ones.

Highlights of the Upcountry Winter Fest include:

• Holiday Craft Fair hosted by Nā Aliʻi Football: Stroll through a charming market of local artisans and holiday vendors offering unique gifts.
• Farmers Market: The community’s greenest thumbs will have locally grown produce and plants available for purchase.
• Food Trucks and Booths: Fuel your holiday walk through campus with offerings from multiple food trucks and booths manned by the many school organizations participating in this event.
• Live Music & Entertainment: Enjoy live performances from local musicians and entertainers, including the Nā Aliʻi Big Band, Zenshin Daiko, V.I.V. & Band, and Nuff Sedd
• Visit with Santa: Children (and adults) can meet Santa Claus and Mrs. Claus for photos and to share their holiday wishes. A mailbox with express service to the North Pole will also be available to those that want to make extra sure that the elves get their wish lists.
• Holiday Display: Delight in a walkable holiday display featuring beloved holiday characters expertly portrayed by student volunteers from the King Kekaulike Drama and AVID Clubs.
• Keiki Games: Keep the keiki engaged with games and prizes operated by participating school organizations.
• Non-Profit & Business Booths: Get to know local nonprofit organizations and businesses that help make the community thrive.

In addition to the wide range of events and activities, Upcountry Winter Fest will serve as a silent auction pick up spot, with the online auction live until Nov. 22, 2025.  Auction items can be found at bit.ly/khsf2025auction. Proceeds go towards scholarships for King Kekaulike High School students and includes many gift certificates featuring local family restaurants to fine dining experiences; opportunities for adventures such as a guided hiking tour and a sunset and celestial cruise; a hotel accommodation and cabana rental; and featuring beautiful pieces from the Rachael Ray Art Collection.

“We are so excited to bring this festival back for another year,” said the Kekaulike High School Foundation, the festival’s host organization. “The Upcountry Winter Fest is about more than just celebrating the season. It’s about bringing people together in a way that’s accessible, fun, and family-oriented. We look forward to seeing everyone, from long-time residents to first-time visitors, come together to enjoy the magic of the holidays.”

With help and support of our community, admission and parking at the Upcountry Winter Fest are free. Parking is available through the Kula Highway gate of the school campus.

This event is supported by the County of Maui, the Office of Economic Development, and the Nuestro Futuro Foundation. The KHSF is grateful to all the generous sponsors who have helped make the event possible: Valley Isle Fencing, Ace Hardware Pukalani, Pukalani Superette, Service Rentals, Pacific Media Group, Goodfellow Bros, Kula Botanical Gardens, and Maui Optix.

For more information on the Upcountry Winter Fest, including the full schedule of events and participants, follow them on Instagram at @upcountrywinterfest and @kekaulikehighschoolfoundation or Facebook at Upcountry Winter Fest and Kekaulike High School Foundation.