Kailua is host to all kinds of entertaining and tasty events throughout the year. From summer concerts to block parties and parades, residents and visitors enjoy gathering for entertainment, fun and food in cool, quiet Kailua.
Cool Kailua Nights
Cool Kailua Nights is an annual block party held in October in Kailua Town Center at the Whole Foods Market parking lot. Some 15,000 residents and visitors turn out for the party and health awareness fair, featuring great food, top Hawaii entertainers and a variety of fun events, such as a doggy fashion show. (Proceeds benefit the Boys & Girls Club of Hawaii Windward Clubhouse and Castle Medical Center’s Oncology Unit.) Get more information.
Kanikapila in Kailua
The Harold K.L. Castle Foundation recently launched this popular monthly music series celebrating Hawaiian music and the culture of Windward Oahu. It is held one Saturday each month from 4 to 5:30 p.m. on the second floor of the open-air parking garage near Whole Foods Market in Kailua Town. Attendees are encouraged to bring their own chairs, grab food from their favorite Kailua eatery, and sit back and relax. Get more information.
I Love Hula
The popular “I Love Hula in Kailua” hula series features many of the hula halau and kumu hula with roots in or near Kailua. The Harold K.L. Castle Foundation is sponsoring the free hula series, which will feature 10 hula halau throughout the year. The hula performances take place on most second Sundays from 3 p.m. to 4 p.m. in Kailua Town Center between Macy’s and Pier 1. (Some performances may be held in the parking garage). Get more information.
Kailua July 4th Parade
For more than 60 years, Kailua has been celebrating Independence Day with one of the state’s best parades and fireworks displays. Bands, color guards, churches, scouts, clubs, dance studios, floats, war veterans and politicians parade through Kailua Town during this patriotic celebration. Get more information.
Whether you’re watching or participating in the annual Lanikai Triathlon, Kailua is the place to be in April. The triathlon – a 500 meter (546.81 yards) swim, 20K (12.43 miles) bike and 5K (3.11 miles) run – is fast and fun and tempts athletes of all levels. Get more information.
I Love Kailua Town Party
Sponsored by the Lani-Kailua Outdoor Circle, the annual April “I Love Kailua” Town Party is Kailua’s biggest event of the year. The party features sample cuisine from great Kailua restaurants and vendors, daylong entertainment, arts and crafts, and a plant sale. The event is a celebration to thank residents and visitors for keeping Kailua clean, green and beautiful. (Proceeds from the “I Love Kailua” Town Party pay for major plantings in Kailua and their upkeep.) Get more information.
Kailua Farmers Market
Kailua offers 3 different farmer’s markets that offer a wide variety of local produce and food vendors. The largest is the Thursday evening market with more than 2 dozen vendors selling baked goods, flowers and vegetables.
Times and locations:
Every Thursday from 9:00 to 10:00 a.m.
Kailua District Park at 21 South Kainalu Drive
Every Thursday from 5:00 to 7:30 p.m.
Kailua Town Center Parking Garage at 609 Kailua Road (behind Long’s)
Every Saturday from 4:00 to 8:00 p.m.
Kailua Elementary School at 315 Kuulei Road
Get more information.
Find out more about all Kailua Events here.
Kailua offers residents and visitors some of the best beaches, not only in Hawaii, but in the world! Don’t take just our word for it. Kailua’s two beaches have each been named America’s Best Beach in the annual Top 10 Beach List compiled by coastal expert Dr. Stephen P. Leatherman, aka Dr. Beach. Lanikai Beach was ranked No. 1 in 1996 and Kailua Beach Park in 1998.
Lanikai means “heavenly sea” in Hawaiian and that is exactly what you will find at Lanikai Beach. Warm, turquoise waters brush up against a fine sand beach while gentle trade winds offer cool relief.
Kailua Beach Park
Kailua Beach Park is a favorite of locals and visitors. From sunbathing to kite surfing and kayaking, Kailua Beach offers something for everyone looking to enjoy the sun, sand and sea.
Maunawili Falls Trail
The easy 1.5-mile hike along the Maunawili Falls Trail is a great introduction to Oahu trails. The trail wanders through lush, tropical surroundings – including coffee and mountain apple trees – to a lovely waterfall and swimming hole and offers views into gorgeous gorges. Get more information.
The 10-mile Maunawili Trail runs along the Windward base of the Koolau Mountains, beginning off the Pali Highway and ending in Waimanalo. The terrain varies from wet gulches to forest, and the trail offers spectacular views of the windward side of Oahu, including Mount Olomana and the Koolaupoko Watershed. Get more information.
Kaiwa Ridge (Pillbox) Trail
Kaiwa Ridge Trail climbs up the ridge behind Lanikai. It leads through native and introduced coastal vegetation and ends at a World War II bunker, one of the defensive “pillboxes” built after the bombing of Pearl Harbor. The trail offers 360-degree views of Kailua, Lanikai, the Mokulua Islands and the Koolau Mountains. Get more information.
Kawainui Marsh Trail
Stretching about three miles through Kailua wetlands, the Kawainui Marsh trail is a peaceful oasis right outside the hum of Kailua Town. Consisting of a level gravel access road and a paved sidewalk, this family-friendly trail is great for walking, jogging, biking and strollers. Get more information.
Na Pohaku o Hauwahine Historical Site
Na Pohaku o Hauwahine is also known as the “rock formation of the Hawaiian Mo‘o goddess and guardian of Kawainui Marsh.” The rock itself is found in a gem of a little park set in an unusual and changing landscape of lovely views and native Hawaiian plants that volunteers are reintroducing into the area. Get more information.
With its generally flat topography and quiet beachside-community feel, biking in and around Kailua is a great way to get exercise, commute or just explore the delights of this windward community. Miles of bike paths take riders along beachfront roads, through the town center and around the loop in Lanikai. See the Kailua Bike Map.
Find out more about Hiking & Biking in Kailua here.
Kailua may seem like a quaint and quiet hidden beachside treasure but there are a lot of things going on, especially if you like organized outdoor activities. Canoeing, golfing, volleyball and tennis clubs abound!
Kailua Canoe Club
Novice to expert members of the Kailua Canoe Club take part in a variety of events, races and regattas. The club’s mission is to support paddling and other ocean activities, create a sense of family and community, and teach members to love and respect the ocean and water sports. Membership, activities and race information.
Lanikai Canoe Club
Lanikai Canoe Club’s mission is to maintain and perpetuate Hawaiian culture through the promotion of competitive and recreational outrigger canoe paddling for youth, family and the community. Registration takes place at various times of the year for the different paddling activities offered. Membership, activities and race information.
Kailua Racquet Club
The Kailua Racquet Club bills itself as “the best tennis club this side of the Mississippi.” A member-owned, private tennis club, it is nestled in the heart of a coconut grove in a quiet neighborhood. It includes nine tennis courts, clubhouse, pool and Kaminski’s Café, open to members and their guests. Membership, activities and information.
Mid Pacific Country Club
Located in Lanikai, the private Mid Pacific Country Club has provided members with spectacular views, first-class golf and a retreat from everyday life for over 83 years. The highly acclaimed golf course has hosted some of the finest golfers in the world, and the large clubhouse provides unrivaled entertainment venues. Membership, activities and information.
These are in the Kailua area and open to the general public:
Bay View Golf Park
Koolau Golf Club
Luana Hills Country Club
Olomana Golf Links
Pali Golf Course