Originality and creative concept Workmanship and use of materials and color General presentation Lights and nighttime appeal
Those are the four judging criteria for the 2026 Kailua Kalikimaka Window Decorating Contest. The Kailua Village Business Improvement District runs it and labels it "NEW!" this year. The last line is the one to plan around. The district's guidelines say it directly: "Consider lighting up your windows at night."
This year, shopkeepers will be scored partly on how their windows look once the sun goes down. Judging starts December 1, and the winners will be named at the Christmas parade on December 12. That makes evening the main time for holiday décor in Historic Kailua Village this year, and it gives the first eleven evenings of December a schedule they didn't have before.
How the Contest Works
The district wants to "entice community members to shop small and shop local in Historic Kailua Village." The contest is open to business owners and shopkeepers inside the district, and it costs nothing to enter. This year's theme is "Kailua Kalikimaka."
The prize money is real. A judging panel awards $1,500 for first place, $1,000 for second and $500 for third. The entry deadline is 5 p.m. on Friday, November 13. Windows have to be finished by Monday, November 30, and stay decorated through December 31. Only décor visible from outside counts, so everything being judged can be seen from the sidewalk.
The entry form asks shopkeepers to check off special features. The choices are animated elements, handmade props, LED or fairy lights, and music or sound. Every window also has to carry its own theme title and a short description. Expect windows with moving pieces, handmade props and lights meant to be seen after dark.
You can read the full rules on the district's contest page. The rules point to HistoricKailuaVillage.com for the district's boundaries. The simplest way to think of it is the historic stretch of Aliʻi Drive and the shops around it.
Eleven Evenings Before the Winners Are Named
Judging starts Tuesday, December 1, and the winners will be announced during the Kailua Village Christmas Parade on December 12. Between those dates, the windows are at their freshest, and nobody knows yet who has won. A walk on any of those evenings shows you every entry before the judges' picks are public.
The windows aren't the only lights going on at the start of the season. The district's 2026 events magazine lists the Kailua Kalikimaka Tree Lighting for November 27 at 5 p.m., the Friday after Thanksgiving. That's three days before the windows have to be finished. When Big Island Now covered the 2022 season, the tree stood at Emma's Square, and the lighting included a performance by Kapulanakēhau Tamure and keiki hula from Hālau E Hulali Mai I Ka Lā.
Parking in the village is a challenge on a regular weeknight and gets harder in December. Our earlier post on how the Kona Trolley fits with the free bus and the paid lots lays out your options for getting downtown without circling for a space.
Across the Street, the Palace Has Its Own Trees
Huliheʻe Palace is putting up its own holiday displays this year. The Daughters of Hawaiʻi are running Kulāia: A Season of Celebration from November 1 through December 30 at Huliheʻe and at Hānaiakamalama, their palace in Nuʻuanu on Oʻahu. The program includes Kulāia Holiday Gift Shops, Christmas teas, workshops and special evening tours.
The palace display has a lot in common with the windows across Aliʻi Drive. The Daughters' announcement says the palace will be "adorned with Kulāia Christmas Trees, decorated by invited community organizations, each sharing their own creativity, traditions, and aloha with all who visit." Shopkeepers decorate the storefronts, and community groups decorate the palace trees. Both draw people to the same few blocks, and the palace's evening tours add an after-dark stop of their own.
The Huliheʻe workshop series features Hawaiʻi Island practitioners. Kumu Kawaihili Uyeshiro of Ko Kawai Lei teaches Hawaiian wreath-making, and Loea Lauhala Glenda Freitas leads a lauhala ornament class rooted in Kona's weaving traditions. On Sunday, November 22, from 10 a.m. to 12:30 p.m., Kumu Hula Ipolei Lindsey-Asing of Hālau Nāwehiokaipoaloha teaches Hula for the Holidays. Reservations go through the Daughters of Hawaiʻi's Kulāia page.
December 12 Is Also the Awards Night
The Kailua-Kona Community Parade Association has set the Kailua Village Christmas Parade for Saturday, December 12, 2026, at 5:30 p.m. This year's theme is "Mele Kalikimaka Magic." The district's events magazine says the parade winds "through the heart of Kailua Village from Kona Gym to Coconut Grove Marketplace."
The parade has deep roots. Big Island Now called the 2022 parade the 36th annual, presented by the Rotary Clubs of West Hawaiʻi and the Kailua-Kona Community Parade Association. In 2024, Big Island Now reported that the parade started at the Kekuaokalani Gymnasium parking lot near the Kona Community Aquatic Center. It then went along Kuakini Highway to Palani Street and down Aliʻi Drive through the village, with Hawaiʻi Island Food Basket volunteers collecting food donations along the way.
This year the parade is also when the contest ends. Anyone who has walked the windows over the previous eleven evenings will already have a favorite when the winners are read out. The parade association's site also has an entry form and a donation link for anyone who wants to march or support the event.
Palace fans can make a full day of it. The Huliheʻe Christmas Tea is set for that same Saturday, from 11 a.m. to 2 p.m., and the Daughters of Hawaiʻi say details are coming soon. At their Oʻahu palace tea on December 6, seats start at $100 each. Both teas help pay for the palaces' preservation and daily operations.
The Sunday After
The day after the parade, Aliʻi Drive closes to cars. Kokua Kailua, the district's monthly village stroll, runs Sunday, December 13, from 1 to 6 p.m. The district bills this edition as "Kailua Kalikimaka." The pedestrian zone runs from Kailua Pier through Historic Kailua Village to Hualālai Road. Expect more than 100 vendor booths with local artisans, crafters, musicians and merchants, and leashed dogs are welcome.
The stroll is the one chance to see the decorated windows from the middle of Aliʻi Drive with no traffic. It's also when the shops behind those windows are busiest, which is the point of a contest built around shopping local. The district's events magazine also schedules a Kailua Kalikimaka Concert at 4 p.m. at Emma's Square and a Lighted Boat Parade at 6 p.m. at Kailua Pier as part of Kailua Kalikimaka Sunday. The boat parade is scheduled for the hour the stroll ends, so the pier is the natural last stop of the day.
Here's the season in order, using the dates published by the organizers above:
- November 22, 10 a.m. Hula for the Holidays workshop at Huliheʻe Palace.
- November 27, 5 p.m. Kailua Kalikimaka Tree Lighting, per the district's 2026 magazine.
- November 30. Contest windows must be finished.
- December 1. Judging begins, and the windows stay up through December 31.
- December 12, 11 a.m. Huliheʻe Christmas Tea.
- December 12, 5:30 p.m. Kailua Village Christmas Parade, with window contest winners announced.
- December 13, 1 to 6 p.m. Kokua Kailua stroll on a car-free Aliʻi Drive, with a 4 p.m. concert at Emma's Square and a 6 p.m. Lighted Boat Parade at Kailua Pier on the magazine schedule.
- December 30. Kulāia wraps up at Huliheʻe Palace.
For more of the village beyond December, our Kona shopping guide and Kona neighborhood guide cover the shops and blocks that will have their windows lit this month.
If you're hosting family from the mainland this December and want help planning an evening in the village, from where to start your walk to when to reach the pier for the boats, Kristina Vaughn-Hazard would be glad to share what she knows of Kailua Village. Schedule a personalized Kona consultation, and let's talk about the season over coffee.
