Upcountry Winter Fest

The much-anticipated Upcountry Winter Fest presented by the Kekaulike High School Foundation (KHSF) is returning this year, bringing a sparkling array of winter activities, live entertainment, and seasonal delights to the heart of the Upcountry. 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.

Taking place on Saturday, November 29, 2025 from 3:00 pm to 8:00 pm, 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 Na Ali’i Football: Stroll through a charming market of local artisans and holiday vendors offering unique gifts.

Farmers Market: Our 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 Na Ali’i 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 non-profit organizations and businesses that help make our community thrive.

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

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