Who Actually Puts On Kailua's Holiday Season

"Praise the parking directors for staying out in the hot sun all day directing traffic!"

A vendor wrote that about the 2023 Lanikai Craft Fair, and it's on the Lanikai Association's own page for the event. The praise goes to volunteers, which fits the whole Kailua holiday calendar. Most of the dates between now and the end of December come from a neighborhood association, a business improvement district and community groups, and much of what they raise or promote stays in town.

The Fair That Pays for the Beach Paths

This year's Lanikai Craft Fair is on Saturday, November 21, at Lanikai Park. Volunteers run it, and it hosts about 84 vendors, which the association says suits the community park well.

The money is what sets this fair apart from a typical holiday market. It is the Lanikai Association's primary fundraiser for maintaining Lanikai Park and the Lanikai beach rights of way, the paths between houses that lead down to the sand. The 2024 fair made more than $18,000 in profit, all of which went to the upkeep of the association-owned park. More than 80 volunteers worked the 2023 fair.

The fair began small. The first one was held in December 1988 with about 30 vendors, and a summer fair followed in 1989. Before that, the park's main fundraiser was an annual luau. Preparing it meant gathering luau leaves, decorating a large tent, working the imu and staying overnight at the park to guard the pigs as they baked. The association later dropped the May fair to put its volunteers into one large Christmas fair. 2020 is the only year it has skipped.

So a purchase at a booth in Lanikai Park on the 21st goes partly toward keeping the beach access paths usable in March.

Historic Kailua Village Adds a Contest of Its Own

The town's business district runs the same kind of effort a few blocks inland. The Kailua Village Business Improvement District is sponsoring the 2026 Kailua Kalikimaka Window Decorating Contest, which the district marks as new this year. Its stated goal is to encourage community members to "shop small and shop local in Historic Kailua Village."

The timeline:

1. Business owners and shopkeepers in the district submit entries by 5 p.m. on Friday, November 13.
2. Judging begins Tuesday, December 1, and decorated windows must stay up through December 31.
3. A judging panel names first, second and third place.
4. Winners are announced at the Kailua Village Christmas Parade on December 12.

The rules require windows to stay decorated for all of December, so the contest lasts a month. From December 1 through New Year's Eve, a walk through the village core passes storefronts dressed for judging, with the theme "Kailua Kalikimaka." The parade on the 12th serves as the contest's awards night.

Uluniu Street on a Sunday Morning

The Sunday routine centers on one stretch of Uluniu Street. Lōkahi Kailua Market sets up at 340 Uluniu Street every Sunday from November 8 through December 27, 9 a.m. to 1 p.m. Go Hawaii's event listing describes food, artisans, farm goods, music and activities. That's eight Sundays in a row, and the last one falls two days after Christmas.

Just up the street at 315 Uluniu is Cinnamon's Restaurant, which Puna and Cricket Nam opened in Kailua Square in 1985. Their son Alika Nam now runs it, as the Honolulu Star-Advertiser reported on October 21. Cricket baked wedding cakes from home before the restaurant opened, and she chose the name Cinnamon's. Her recipes are now sold at Cinnamon's SweetShop, which Alika opened across from the restaurant. The same article says a retail shop is in the works for part of the restaurant space.

Together they make a short holiday-season Sunday: the market at 340, then a bakery box from across the way. Both are run by people who live and work in Kailua.

A Second Parade, Inland

The Kailua Village Christmas Parade isn't the only one on the calendar. The Kailua Neighborhood Board's October 1 meeting summary lists the annual Olomana Christmas parade for Sunday, December 20, starting at 2 p.m. at Maunawili Elementary School.

The two parades sit eight days apart, and each covers a different part of town. The December 12 parade is tied to the village shops and their windows. The December 20 parade starts at the elementary school on the Maunawili side. Families on each side of Kailua get a parade close to home.

The Street Work Happening Around the Festivities

The city and private developers are also making changes in the same blocks where the holiday events take place. None of it changes the December calendar, but some of it will be visible on the way to these events.

• Kailua Municipal Parking Lot. The city's Department of Design and Construction ran the last phase of an archaeological survey at the lot from November 2 through 6. The work was originally due to finish in April but was delayed by the March Kona Low. Its purpose is to find out whether culturally or historically significant resources are present before construction. The city's notice says improvements could begin at the end of 2027: new asphalt, upgraded lighting, accessibility improvements, better pay stations and new landscaping. The city named 25 Aulike Street, across the street, as alternate public parking.
• Kuʻulei Road and Aulike Street. The Department of Transportation Services plans "quick-build" pedestrian improvements at this intersection as an interim step before a planned traffic signal. Each crossing gets a pedestrian refuge island and curb extensions, and the school-zone speed limit drops to 20 mph. According to the city's Complete Streets page for Kailua, installation was expected to begin in November and take one to two weeks, weather permitting.
• Hāmākua Drive and Hahani Street. A Chick-fil-A is planned for this corner, and KHON2 reported that construction is planned to begin in 2028. The draft environmental assessment lists the parcels as 164, 170 and 174 Hāmākua Drive and 380 Hahani Street. It calls for demolishing the existing structures and building a restaurant with a two-lane drive-through.

KHON2 also reported on local reaction to the Chick-fil-A plan. Kailua Neighborhood Board chair Bill Hicks described the leased parcels as the Midas parcel, the former Bob's sports bar that is now Lava, and two lots behind them currently used for parking. He told the station, "I'm sure it will be popular. The concern is it will be so popular that it leads to congestion on the adjacent streets." Rep. Lisa Marten pointed out that the site is next to Hamakua Marsh and stressed care with runoff during construction and once the drive-through opens.

The Lanikai Craft Fair and the window contest come from a volunteer association and a business district. The parking lot, the crosswalk and the corner lot are not, and these are the projects that will reshape downtown Kailua after the decorations come down.

The Season on One Page

At Fortune Hawaii Realty, we follow how Kailua's community groups and city projects shape the town between Uluniu Street and Lanikai Park, and we're happy to talk through what those changes mean for your home or your next move. Book an appointment, and we can meet after the market on a Sunday morning.