The holiday season is upon us in Kailua, and we’ve got a lineup of festive events and special promotions to make it the most wonderful time of year. Whether you’re shopping for gifts, enjoying live music, sipping on something seasonal or taking a photo by the Christmas tree, there’s something for everyone. Mark your calendars!
NOVEMBER
November 22 – 30
Shop Small Kailua Gift with Purchase
Support our local shops and get rewarded: spend a combined total of $150 or more at participating Kailua Town merchants and receive an exclusive Shop Small Kailua microfiber beach towel for FREE*. It’s our way of saying mahalo for shopping local this holiday season.
*Available while supplies last
November 27 – 30
Black Friday & Small Business Saturday Deals
Kick off the holiday season in Kailua Town with unbeatable Black Friday savings and Small Business Saturday specials from your favorite local merchants! Whether you’re grabbing gifts, treating yourself, or supporting local restaurants, this is the perfect weekend to shop small in Kailua.
DECEMBER
All Month Long
Kailua Town Christmas Tree
Lau Hala Shops Lobby
Capture the magic of the holidays with the festive Christmas Tree display inside the Lau Hala Shops lobby! The beautifully decorated tree will be up all month long; perfect for family photos, selfies with friends, or just taking a moment to soak in the holiday spirit.
December 3 | 5 – 9pm
Free Trolley Service for Adventist Health Castle’s Christmas Tree Lighting
Lau Hala Shops Parking Lot
Enjoy a stress-free way to celebrate! Ride the free holiday trolley to Adventist Health Castle’s annual Christmas Tree Lighting event and enjoy a magical night of lights, music, and holiday cheer.
December 5 | 5 – 6pm
Christmas Concert with Windward Choral Society
Kailua Town Center Parking Garage
Get into the holiday spirit with the Windward Choral Society at this festive community sing-a-long! Bring your friends, family, and best singing voice — this free event is all about spreading joy and aloha through music.
December 11 | 4 – 7pm
Holiday Sip + Shop
Lau Hala Shops Lobby
Sip, shop, and celebrate! Our annual Holiday Sip + Shop event invites you to explore local boutiques, enjoy festive refreshments, and find the perfect gifts; all while supporting Kailua’s small businesses.
