Lei Day Celebration

Lei Day, established in 1927 and officially recognized in 1929, is a cherished Hawaiian tradition dedicated to the art of lei-making and the spirit of aloha. Each island in Hawaii has its unique lei and associated color, symbolizing its distinct identity. Oahu, for instance, is represented by the golden-yellow ʻilima flower. The festivities at Kapiʻolani Park commence at 9:00 AM and extend throughout the day, featuring live music, hula performances, and the prestigious lei-making competition, where artisans showcase intricate and fragrant creations. The event also includes the crowning of the Lei Queen and her court, symbolizing the embodiment of Hawaiian grace and culture. Attendees are encouraged to wear or create leis, immersing themselves in this vibrant cultural expression.

When: May 1, 2026

Where: 3840 Paki Ave, Honolulu, HI 96815 (Kapi’olani Park)

Flores de Mayo & Filipino Fiesta

Flores de Mayo, translating to "Flowers of May," is a traditional Filipino festival honoring the Blessed Virgin Mary. In Hawaii, this celebration has evolved into the Filipino Fiesta, the largest gathering of the Filipino community on Oahu. Held from 10:00 AM to 6:00 PM, the event offers a deep dive into Filipino culture through authentic cuisine, traditional dance and music performances, cultural exhibits, and a marketplace featuring local artisans and businesses. A highlight is the Santacruzan procession, a reenactment of Queen Helena's search for the Holy Cross, showcasing participants in elaborate traditional attire. This annual celebration emphasizes the cultural significance of Filipino heritage in Hawaii through traditional cuisine, performances, and community gatherings.

When: May 2, 2026

Where: Filipino Community Center, Waipahu

More Info: Filipino Fiesta

Ko'olina Artfest

Every Wednesday in May, the picturesque Ko'olina Beach Lagoon transforms into an open-air gallery from 9:00 AM to 5:00 PM. The Ko'olina Artfest features over 40 local artists who are displaying and selling their creations, ranging from paintings and sculptures to handcrafted jewelry and textiles. Accompanied by the soothing sounds of Hawaiian slack-key guitar and ukulele performances, attendees can engage with artists, gain insights into their creative processes, and purchase unique pieces that capture the essence of Hawaiian artistry.

When: May 6, 13, 20, and 27, 2026

Where: Ko'olina Beach Lagoon #3

KCC Farmers Market

A Saturday morning staple for locals and visitors, the KCC Farmers Market operates from 7:30 AM to 11:00 AM. Beyond offering a wide array of fresh, locally grown produce, the market is renowned for its diverse food stalls. Patrons can savor delicacies such as grilled Kona abalone, roasted Kahuku corn, and an assortment of tropical fruits. The market also features stalls selling island flowers, artisanal products, and unique Hawaiian treats like Ono Pops, making it a gastronomic adventure and a celebration of Hawaii's agricultural richness.

When: May 2, 9, 16, 23, and 30, 2026

Where: Kapiʻolani Community College, near Diamond Head

More Info: Farmers Market

Kū Haʻaheo Live Music Series

Every Tuesday afternoon, the Waikīkī Beach Walk hosts the Kū Haʻaheo concert series, a free event that immerses audiences in traditional Hawaiian music and dance. The series features the award-winning duo KAMANAWA, comprising Blaine Kia and Kalei Kahalewai, alongside dancers from Hālau Ka Waikahe Lani Mālie. Attendees are treated to authentic hula performances and mele (songs) that narrate stories of Hawaiian history, legends, and the islands' natural beauty, fostering a deeper appreciation for Hawaii's rich cultural tapestry.

When: May 5, 12, 19, and 26, 2026

Where: Waikiki Beach Walk

Honolulu Triathlon

The Honolulu Triathlon is a premier athletic event that attracts participants worldwide. The race encompasses a 1.5 km swim in the clear waters off Ala Moana Beach, a 40 km bike ride along Oahu's scenic coastal routes, and a 10 km run through Honolulu's urban landscape. The event caters to various age groups and skill levels, including a children's race and relay teams. Spectators can cheer on athletes from designated viewing areas, experiencing the communal spirit and determination that define this challenging competition.

When: May 17, 2026

Where: Ala Moana Beach Park and surrounding areas

More Info: HONTRI

50th State Fair

A beloved annual tradition, the 50th State Fair offers classic carnival attractions infused with a Hawaiian twist. Attendees can enjoy thrilling rides, indulge in various local and traditional fair foods, and partake in games suitable for all ages. Beyond the midway, the fair features live entertainment, including concerts by local musicians, dance troupes, and comedic acts. Agricultural exhibits and educational booths provide insight into Hawaii's farming traditions and sustainability efforts. The fair's lively atmosphere is ideal for families, couples, and groups looking to soak in community spirit while enjoying a festive environment. With its affordable pricing and island-style flair, the 50th State Fair is a nostalgic and joyful kickoff to Oahu’s summer season.

When: Late May through early July 2026 

Where: Aloha Stadium, Honolulu

More Info: State Fair

May on Oahu is a vivid tapestry of celebration, culture, and community. As spring blossoms into early summer, the island offers a dynamic mix of festivals, arts, cuisine, and sporting events—each rooted in local traditions or infused with the rich diversity of its people.