The Kekaulike High School Foundation is bringing back its Upcountry Winter Fest on Nov. 28, with free admission and parking at the King Kekaulike High School campus in Pukalani from 3 to 8 p.m. The afternoon-into-evening event is shaping up as a one-stop holiday outing for Upcountry families, mixing a craft fair and farmers market with food trucks, live music and games built around student volunteers.
According to Maui Now, the fest will feature a holiday craft fair, farmers market, food trucks and booths staffed by school organizations. Live entertainment is set to include the Nā Aliʻi Big Band, Zenshin Daiko and V.I.V. & Band, giving the campus a full lineup of music to go along with the shopping and snacking. The Kekaulike High School Foundation describes the gathering on its event page as including food, entertainment, a craft fair, a business tent, a farmers market and a holiday display built for photos.
Kendama Tournament, Santa Visits and a Letter to the North Pole
Kids and teens will have plenty to do beyond the vendor tables. The festival includes a student kendama tournament, and school organizations will run keiki games with prizes, the same report notes. Children can also take photos with Santa and Mrs. Claus, and there will be a mailbox on-site for letters addressed to the North Pole.
King Kekaulike Avid Club student volunteers are set to portray holiday characters in a walkable display, adding a homegrown touch to the seasonal scene. Local nonprofits and businesses will staff information booths throughout the grounds, rounding out a lineup meant to spotlight both student talent and Upcountry community groups.
Auction Items Include Goat Yoga and a Guided Hike
The festival also doubles as the pickup location for the foundation's online silent auction, which runs through Nov. 21. Proceeds from the auction go toward scholarships for King Kekaulike High School students, per the foundation. Items up for bid include restaurant gift certificates, a guided hiking tour, private music lessons and goat yoga, offering a quirky range of options for Upcountry bidders.
The foundation says it has facilitated more than $34,500 in scholarships since 2022 and directly funded an additional $14,500 for students pursuing higher education. It has also awarded more than $8,000 in grants to more than 30 staff members across the Kekaulike school complex, underscoring the fundraiser's reach beyond just the student body.
Free Parking Through the Kula Highway Gate
Organizers say the event is made possible with support from the County of Maui, its Office of Economic Development, and the Nuestro Futuro Foundation. The foundation's event page states the festival aims to provide participants with an economic opportunity and to highlight Upcountry businesses, services and products, and organizers are still seeking craft fair, farmers market, keiki games and food truck vendors to join the lineup.
Last year's Upcountry Winter Fest followed a similar formula, running Nov. 29, 2025, from 3 to 8 p.m. with free admission and parking available through the campus's Kula Highway gate. That 2025 edition also paired a craft fair and farmers market with food trucks, live entertainment, Santa visits and a holiday display, and listed sponsors including Valley Isle Fencing, Ace Hardware Pukalani, Pukalani Superette, Service Rentals, Pacific Media Group, Goodfellow Bros., Kula Botanical Gardens and Maui Optix. This year's event is expected to follow that same free, family-friendly format on the King Kekaulike campus.
