When you buy a wreath, a jar of honey or a plate lunch at an Upcountry holiday fair this year, where does the money go? At every fair from November 21 to December 13, it goes to a specific local cause. One fair funds classroom programs, one funds tuition assistance, one raises scholarship money for high school students through its auction, and one funds a children's advocacy nonprofit. The organizers' own pages say so.
The four events don't overlap on the calendar. Three fall on consecutive Saturdays, and the fourth, at ʻUlupalakua Ranch, is on a Sunday the following weekend. With no two fairs on the same day, you can go to all four, and the order you go in decides where your holiday budget ends up.
| Date | Event | Where | Hours | Proceeds go to |
|---|---|---|---|---|
| Sat., Nov. 21 | Kula School Harvest Festival | Kula Elementary, 5000 Kula Hwy | 9 a.m. to 3 p.m. | Kula School academic and enrichment programs |
| Sat., Nov. 28 | Upcountry Winter Fest | King Kekaulike High School, Pukalani | 3 to 8 p.m. | Online auction funds King Kekaulike student scholarships |
| Sat., Dec. 5 | Haleakalā Waldorf School Holiday Faire | 4160 Lower Kula Rd. | 9 a.m. to 4 p.m. | Tuition Assistance Program |
| Sun., Dec. 13 | Christmas in the Country | ʻUlupalakua Ranch | 10 a.m. to 3 p.m. | Friends of the Children's Justice Center of Maui |
The two oldest fairs were built by school families
Two of these fairs have run for decades, and both started as school fundraisers staffed by parents.
The Haleakalā Waldorf School Holiday Faire started in 1985. According to the school's fundraising page, it is the school's top fundraiser and usually falls on the first Saturday of December. The same page says that "100% of the funds raised go towards our Tuition Assistance Program" and that "All parents are required to volunteer at this event." This year's date, December 5, appears on the school's 2026 to 2027 calendar.
The Kula School Harvest Festival is almost as old. Maui Now called the 2018 edition the 31st annual festival and described music, a restaurant row, a country store, vendors, games, bouncy castles, hay and pony rides and a petting zoo. The organizers' 2026 page keeps the same shape and says all proceeds "go directly back to Kula School students through academic and enrichment programs."
Because families run these fairs, families also show up in the attractions. On the Harvest Festival's attractions page, Pre-K families care for the petting farm's turkeys, mini horses, ducks and sheep. The country store sells farm-grown produce, plants and baked goods, and the silent auction offers themed baskets put together by each classroom. At last year's festival, Kula Elementary students performed alongside Hula Hālau Wehiwehi O Leilehua, Kaina Kountry, Nuff Sedd, Sione Liti and Kalama Ukulele.
Saturday, Nov. 21: Start on Kula Highway
The Harvest Festival is the first of the four, and it is the most farm-focused. Beyond the petting farm and country store, the organizers list pony rides, face painting, games, local artisan stalls and a "Restaurant Row" of food trucks. The festival runs 9 a.m. to 3 p.m. at 5000 Kula Hwy.
If you want a second stop on the way home, Kula Lodge's food truck and marketplace are open daily from 7 a.m. to 7 p.m. The lodge restaurant is closed indefinitely while it rebuilds.
Saturday, Nov. 28: An evening fair in Pukalani
The second weekend changes the schedule. Upcountry Winter Fest, run by the Kekaulike High School Foundation, starts at 3 p.m. and runs until 8 p.m. at King Kekaulike High School. Admission and parking are free, and Maui Now reports that parking is through the Kula Highway gate.
This is the only fair of the four that runs into the evening. The music lineup is the Nā Aliʻi Big Band, Zenshin Daiko and V.I.V. & Band. There will also be a student kendama tournament, a holiday craft fair, a farmers market, food trucks, food booths run by school groups, and photos with Santa and Mrs. Claus.
The fest's silent auction starts before the fest does, and its proceeds go toward scholarships for King Kekaulike students. Bidding runs online through Nov. 21, the same day as the Kula Harvest Festival, and you pick up items at the fest itself. Items include restaurant gift certificates, a guided hike, private music lessons and goat yoga.
Because the fest starts late, you can fit a morning in first. The Upcountry Farmers & Crafters Market runs Saturdays from 7 to 11 a.m. at Kulamalu Town Center in Pukalani, with Kula-grown produce, honey, protea and tropical flowers, baked goods and crafts, according to KHON2's market guide.
Saturday, Dec. 5: The faire built around making things
The Waldorf Holiday Faire is the hands-on fair. According to the school, the day opens with a morning elf parade, and every child in an elf costume gets a free gift. Families can make wreaths, dip beeswax candles and make ornaments. There is also a petting zoo, a puppet show, an obstacle course, a bake shop, fresh-squeezed lemonade and juices, local and international craft vendors, a farmers market, live music, hula and class performances.
When Maui Now listed the 2022 faire, its 37th, it counted more than 75 artisans, along with candle dipping, gnome-garden making and a puppet theatre. This year's faire runs 9 a.m. to 4 p.m. at 4160 Lower Kula Rd.
If you are planning to make a wreath, this is the weekend for it. December 5 is early enough that a wreath made at the faire will be up for most of the season.
Sunday, Dec. 13: The newest fair, on a working ranch
Christmas in the Country at ʻUlupalakua Ranch is the youngest of the four. Maui Now reported in October 2025 that the first event, in 2024, raised more than $10,000 for Maui charities. The ranch's events page says last year's event raised more than $7,500 in charitable contributions.
The ranch fair is the only one of the four that doesn't fund a school. For 2026, the ranch has named Friends of the Children's Justice Center of Maui as its nonprofit partner, returning from last year. This year's fair is on Sunday, December 13, from 10 a.m. to 3 p.m. Last year it fell on Saturday, December 13.
Maui Now's coverage of the 2025 event gives a sense of the day. Last year it had more than 45 local craft, food and retail vendors, photos with Santa, hayrides, live music, a petting zoo, keiki activities, a silent auction and paniolo sheep-herding demonstrations. Proceeds went to Maui Food Bank and Friends of the Children's Justice Center of Maui, and the ranch asked guests to bring canned goods for an onsite food drive. Parking was free, and families who arrived before 11 a.m. got free premium parking.
The ranch says the 2026 details will be posted on its events page and Instagram. On regular days, the Ulupalakua Ranch Store is open 10 a.m. to 5 p.m. Tuesday through Sunday, the grill serves from 11 a.m. to 4 p.m. with last call at 3:30, and both are closed Mondays.
Planning the run
You can plan the four weekends around which cause you want to support and what kind of day you want:
- Nov. 21, Kula School Harvest Festival. Go for the country store's produce and plants and the classroom auction baskets. If you are bidding on Winter Fest items online, Nov. 21 is the auction's last day.
- Nov. 28, Upcountry Winter Fest. Start with the Kulamalu market in the morning, then go to King Kekaulike in the afternoon for the big band, taiko and the kendama tournament. Park through the Kula Highway gate.
- Dec. 5, Waldorf Holiday Faire. Arrive early for the elf parade, and plan time for wreath-making and candle dipping before the faire closes at 4 p.m.
- Dec. 13, Christmas in the Country. This one is on a Sunday. Last year, families who arrived before 11 a.m. got free premium parking, and the food drive took canned goods, so watch the ranch's page for this year's details.
Over four weekends, you'll have supported Kula School's enrichment programs, King Kekaulike student scholarships, Waldorf tuition assistance and Friends of the Children's Justice Center of Maui.
Riette has followed Upcountry life since 1988, and it would be her pleasure to talk with you about Kula, its traditions and the land around it over the holidays. Riette Jenkins of Coldwell Banker Global Luxury is available whenever you'd like to talk. Contact Riette for a private consultation.
