The first confirmed holiday sale in Upcountry this year starts at 7 a.m. on a Saturday in mid-November. It's run by a preschool on Makawao Avenue. The last one-day event ends at 3 p.m. on a Sunday in mid-December, at a ranch store on the slopes of Ulupalakua, and its proceeds go to a children's advocacy nonprofit. Between those two dates, and through an arts center's gift shop that stays open until Christmas Eve, every confirmed event on the Upcountry calendar is hosted by a school, an arts nonprofit or a ranch partnering with a nonprofit.
In Makawao, Kula and Ulupalakua, the holiday shopping season runs on fundraisers, and each weekend is tied to the organization hosting it. Once you know which weekend belongs to which group, you can plan December around them.
November opens on Makawao Avenue
The St. Joseph Early Learning Center Christmas Craft Fair is on Saturday, November 14, from 7 a.m. to 2 p.m. at 1294 Makawao Ave. Maui Family Magazine's 2026 winter events guide lists a bake sale, food, crafts, vendors, a keiki zone, Santa and music. The magazine files it as a fundraiser.
The early start matters on this street. The County of Maui's Makawao Avenue reconstruction covers about 1.8 miles from Apana Road to Ai Street. In its most recent advisory, posted July 29 and updated August 5, the county said weekday single-lane closures in active work zones would run from 8:30 a.m. to 3 p.m., with the project due to finish in February 2027. A Saturday fair falls outside that weekday window. The county's traffic advisory is the place to check for newer closure notices before you drive.
If the morning carries on into town, Casanova's café at 1188 Makawao Avenue serves breakfast and lunch Monday through Saturday, 8 a.m. to 2 p.m.
The weekend of November 20 and 21 has two anchors
The following weekend is the busiest stretch of the season, with two big draws on back-to-back days.
On Friday, November 20, Hui Holidays opens at the Hui No‘eau Visual Arts Center, 2841 Baldwin Avenue. It runs through Thursday, December 24, Monday through Saturday, 9 a.m. to 4 p.m. For the season the Hui moves its gift shop into the much larger gallery and fills it with Maui artists and makers: ceramics, textiles, jewelry, keiki gifts, ornaments, bath and body goods. The Hui says it aims to add more local vendors every year, and the event has support from the County of Maui Office of Economic Development.
Purchases there support two groups at once, the makers whose work is on the shelves and the Hui as an organization. The same idea drives the trade day at the Made in Maui County Festival, where the point is keeping Maui-made products selling after the event is over. In Makawao, that shelf stays open for five weeks.
The next morning, Saturday, November 21, is the Kula School Harvest Festival, 9 a.m. to 3 p.m. at 5000 Kula Highway. The school's flyer lists free admission, live entertainment, craft vendors, a keiki fun zone, a petting farm, Restaurant Row, a silent auction, a Country Store and community partners. The festival's own site says all proceeds go to Kula School students through academic and enrichment programs. The Country Store sells farm-grown fruit and vegetables, plants and baked goods. Restaurant Row is made up of local food trucks.
The festival has been around for a while. The Maui News 2018 holiday craft fair guide listed it on the Lower Kula School field, sponsored by the Kula School PTA, on the Saturday before Thanksgiving that year too.
That Saturday also overlaps with Kula's regular weekly market. The Upcountry Farmers Market runs Saturdays from 7 to 11 a.m. at Kulamalu Town Center with more than 100 local vendors, and its page shows no schedule change. On November 21, the market's last two hours line up with the festival's first two, both in Kula.
December packs four dates into eleven days
In November the events are a week apart. In December they come almost back to back.
Thursday, December 3, 5 to 8 p.m. The Hui's Kaluanui Holiday Night Market, which the center also calls Hui Holidays First Night, takes over the Kaluanui Estate with sips, bites, the expanded gift shop and vendors who are there for that night only. It's ticketed, and the Hui says ticket details will be announced soon. Of all the Upcountry holiday events, this is the only evening one and the only ticketed one.
Saturday, December 5, 9 a.m. to 3 p.m. The Haleakalā Waldorf School Holiday Faire is at 4160 Lower Kula Road. Maui Family Magazine's event listing lists crafts and vendors, wreaths, a bakery, children's games, a puppet show, entertainment and food. The school's own 2026–27 calendar also has December 5 down as Holiday Faire.
Saturday, December 12, 11 a.m. to 2 p.m. The Hui Holidays Santa Workshop is back in Makawao, with Santa there from 11:30 a.m. to 1:30 p.m. The Hui asks for a suggested donation of $5 per car.
Sunday, December 13, 10 a.m. to 3 p.m. Christmas in the Country at Ulupalakua Ranch wraps up the season. Maui Family Magazine gives the location as 14779 Piilani Hwy in Kula and lists local vendors, food, keiki activities, live music, Santa, hayrides, a petting zoo and paniolo sheep-herding demonstrations.
The ranch is the clearest example of the pattern. Its 2026 nonprofit beneficiary is the Friends of the Children's Justice Center of Maui, which is partnering with the ranch again this year. The ranch says last year's event raised more than $7,500 for charity, and that past events have also filled multiple containers with food donations for families. Christmas in the Country is the only event this season that names both its beneficiary and a dollar figure from last year.
Who each date supports
Put all seven dates side by side and the pattern is easy to see. The hosts are a preschool, a public elementary school, a private school, an arts nonprofit and a working ranch.
| Date | Event | Host | Where the money goes |
|---|---|---|---|
| Sat., Nov. 14 | Christmas Craft Fair | St. Joseph Early Learning Center | Listed as a fundraiser |
| Nov. 20 to Dec. 24 | Hui Holidays | Hui No‘eau Visual Arts Center | Maui makers and the Hui |
| Sat., Nov. 21 | Harvest Festival | Kula School | Kula School student programs |
| Thu., Dec. 3 | Kaluanui Holiday Night Market | Hui No‘eau | The Hui and one-night vendors |
| Sat., Dec. 5 | Holiday Faire | Haleakalā Waldorf School | Hosted by the school |
| Sat., Dec. 12 | Santa Workshop | Hui No‘eau | Suggested $5 per car donation |
| Sun., Dec. 13 | Christmas in the Country | Ulupalakua Ranch | Friends of the Children's Justice Center of Maui |
Geography matters here too. The Hui and St. Joseph are in Makawao. Kula School and the Waldorf school are both on the Kula side. The ranch is the farthest out, and its Sunday date closes the run of one-day events.
A few planning details
- Watch for Night Market tickets. December 3 is the only ticketed date, and the Hui says ticket details will be announced soon.
- Bring small bills for the Santa Workshop. The Hui's December 12 donation is $5 per car, not per person.
- Kula School's festival is free to get into. The money is raised inside, at the silent auction, the Country Store and Restaurant Row.
- Hui Holidays is a weekday option too. It's the only event on the list that runs Monday through Saturday for five weeks, so it's open on days the fairs aren't.
- There's still time for the fall exhibit at the Hui. Mālama Wao Akua closes Friday, November 6, and the Hui's Talk Story Thursday with Koa Plauche is on November 5, from 4 to 5 p.m.
For a look back at the summer side of the same calendar, our August in Upcountry post covered the Hui's summer dates and the Saturday markets. More on the area is in our Upcountry Maui neighborhood guide.
At Maui & Co. Real Estate, we keep this calendar because these fairs fund the places our Upcountry neighbors count on all year. If you'd like to talk about life on the mountain, from Makawao to Ulupalakua, schedule a private consultation and we'll be glad to sit down with you.
