"Christmas windows must remain decorated from December 1 through December 31."
That line comes from the entry rules for the 2026 Kailua Kalikimaka Window Decorating Contest, and it is the most important holiday change in Historic Kailua Village this year. Until now, the village's Christmas came down to a few big nights: a tree lighting, a parade on Saturday and a stroll with a boat parade on Sunday. Those nights are all back in 2026. What's new is a rule that keeps every competing storefront dressed for the whole month, so the quiet Tuesday evenings between events count too.
A contest written around the calendar
The Kailua Village Business Improvement District sponsors the contest and labels it "NEW!" on its own page. The district says the goal is "enticing community members to shop small and shop local in Historic Kailua Village." Entry is free for business owners and shopkeepers inside the district, and the theme is "Kailua Kalikimaka."
The prize money is large enough to get real effort out of shopkeepers. The judges' first-place window wins $1,500, second place wins $1,000 and third place wins $500. Entries close at 5 p.m. on Friday, November 13. Judging starts Tuesday, December 1. Winners will be announced at the Kailua Village Christmas Parade on December 12.
Windows have to be finished by December 1 and stay up for nineteen days after the winners are named. A first-place window will still be in place on New Year's Eve. If you own or manage a shop on Ali'i Drive, you have until that November 13 deadline, and the entry form asks for a theme title, a short description and any lighting or special features.
November: the village warms up
With the contest deadline still ahead, mid-November is mostly about shopping. On Saturday, November 14, the Kona Commons Artisan Market runs from 9:30 a.m. to 3:30 p.m. in the parking lot fronting Jeans Warehouse, with local makers selling gifts, art, crafts and food.
The next afternoon, Sunday, November 15, Kokua Kailua closes Ali'i Drive to cars from 1 to 6 p.m. The pedestrian marketplace runs from Kailua Pier through the village to Hualālai Road. The November listing promises more than 100 vendor booths with local makers, musicians and merchants. Between the market and the stroll, that weekend works well for early gift shopping, and it falls just after shopkeepers have committed their contest entries.
Then the lights go on. The KVBID's 2026 events calendar lists the Kailua Kalikimaka Tree Lighting for Friday, November 27, at 5 p.m., the day after Thanksgiving. The 2026 listing places it in Historic Kailua Village but doesn't name a specific site or program yet. In 2023, the Kona-Kohala Chamber of Commerce described the tree lighting at Emma's Square, across from Hulihe'e Palace, with keiki hula and music. The 2024 event page used the same Emma's Square location. Emma's Square is a good guess for this year, but it's still a guess until the district posts the 2026 details.
December 12 and 13: the judged windows meet the big weekend
Four days after the tree lighting, the contest judging begins, and the village heads toward its two busiest holiday days. Here they are in order:
| When | What | Where |
|---|---|---|
| Sat., Dec. 12, 9:30 a.m. to 3:30 p.m. | Kona Commons Artisan Market | Kona Commons lot fronting Jeans Warehouse |
| Sat., Dec. 12, 5:30 p.m. | Kailua Village Christmas Parade, theme "Mele Kalikimaka Magic," window contest winners announced | Kona Gym to Coconut Grove Marketplace |
| Sun., Dec. 13, 1 to 6 p.m. | Kokua Kailua stroll | Ali'i Drive, Kailua Pier to Hualālai Road |
| Sun., Dec. 13, 4 p.m. | Kailua Kalikimaka Concert | Emma's Square |
| Sun., Dec. 13, 6 p.m. | Lighted Boat Parade | Kailua Pier |
The Saturday parade is run by the Kailua-Kona Community Parade Association. Parades in Kona lists this year's date, time and theme, and groups that want to march must enter by Friday, December 5. According to the KVBID calendar, the route winds through the village from Kona Gym to Coconut Grove Marketplace. Because the winners are announced at the parade, Saturday evening is the first time anyone knows which storefronts won. From that night on, a walk down Ali'i Drive can include a stop at the three winning windows.
Sunday has its own timing quirk. Kokua Kailua usually falls on the third Sunday, October 18 and November 15 this year, but the 2026 dates list puts December's stroll on the 13th. Moving it up a week pairs it with the parade, which is the same Saturday parade, Sunday stroll pattern the village used in 2023. The 2026 calendar calls the day "Kailua Kalikimaka Sunday."
The Sunday schedule follows the route. The stroll runs north to south from Kailua Pier, the 4 p.m. concert is at Emma's Square in the middle of the afternoon, and the Lighted Boat Parade starts at the pier at 6 p.m., right when the stroll closes. If you finish your shopping at the north end around sundown, you're already in place to watch. Historic Kailua Village's 2023 Kailua Mele Kalikimaka page promised "great viewing from Kailua Pier" for that year's boat parade.
After the winners: the second half of December
Most years, the village's holiday events would be over at this point. In 2026 the windows stay up for another eighteen days after Sunday's boat parade, through December 31. That leaves time to walk Ali'i Drive without a crowd, show the winning displays to family arriving for the holidays, or do some last-minute shopping at the stores whose windows you liked.
One more scheduled event falls in that stretch. Kona5K lists the Jingle Bell Beach Run for Sunday, December 20, 2026. Its RunSignup page puts the 5K start at 7:30 a.m. HST in Kailua-Kona. In 2023 the December run started at Coconut Grove Marketplace and included Santa's Keiki Dash for children 6 and under. The 2026 start location hasn't been posted, so check the registration page before race morning.
What's still being finalized
Some details for the season haven't been published yet. For 2026, nobody has posted:
- A specific site or program for the November 27 tree lighting
- The performer for the December 13 concert at Emma's Square
- Registration details for boats in the Lighted Boat Parade, which in 2023 was open to sailboats, powerboats, canoes and kayaks
- Road closures and parking for the December 12 parade. The Parades in Kona road closures page still shows the July 4 parade
- A public list of businesses that entered the window contest
The Historic Kailua Village events page and Parades in Kona are the two places these updates are most likely to appear. The contest is open only to businesses inside the improvement district, and the district's business page links to a boundary map that was last updated in 2018.
At Hawai'i Estates, we love seeing local shopkeepers put this kind of effort into Ali'i Drive, and we'll be walking past the winning windows ourselves after the parade. If December family visits have you wondering what your Kona home is worth these days, get your Instant Home Valuation from Hawaii Estates, LLC.
