Hilo Lei Day Festival

Lei Day, celebrated annually on May 1st, is a heartfelt tribute to the Hawaiian tradition of lei-making, symbolizing love, friendship, and the aloha spirit. The Hilo Lei Day Festival at Kalākaua Park offers attendees an immersive experience into this cherished custom. The festivities commence with an opening ceremony featuring traditional Hawaiian chants and hula performances, setting a reverent tone for the day. Throughout the park, skilled artisans conduct lei-making demonstrations, showcasing techniques passed down through generations. Visitors are encouraged to participate by crafting their leis using a variety of native flowers and materials. The festival also hosts a lei contest, where creations are judged based on craftsmanship, beauty, and authenticity. Complementing the visual and tactile experiences are live musical performances by local artists, offering melodies that resonate with the island's soulful rhythms. This free event celebrates the artistry of lei-making and fosters a deep appreciation for Hawaiian culture and community. 

When: May 1st

Where: Hilo, HI 96720 (Kalakaua Park)

More Info: Lei Day

Kona Orchid Society Mother's Day Show & Sale

For enthusiasts of botany and natural beauty, the Kona Orchid Society's Mother's Day Show & Sale is a must-visit event. Held at the Makaeo County Pavilion, this annual gathering transforms the venue into a mesmerizing display of orchid varieties, each more captivating than the last. Attendees can marvel at rare and exotic species, gaining insights into their cultivation and care from seasoned growers and master gardeners present on-site. The event also emphasizes education, offering workshops on topics such as pest management, including strategies to combat invasive species like the Little Fire Ant. Beyond the visual feast, the show provides an opportunity to purchase unique orchids, making for perfect Mother's Day gifts. Early Bird ticket holders are granted exclusive access an hour before the general public, allowing for a more intimate experience with the exhibits and vendors. 

When: May 2nd

Where: Makaeo County Pavilion, Old Airport Beach Park, Kailua-Kona

More Info: Orchid Society

Hilo Chocolate Festival

Chocolate lovers will find paradise at the 5th Annual Hilo Chocolate Festival. This delectable event celebrates Hawaii's burgeoning cacao industry and the artisans transforming these beans into gourmet chocolates. Hosted at the scenic Hilo Hawaiian Hotel, the festival offers a day filled with indulgence and education. Attendees can take guided farm tours, providing a firsthand look at cacao cultivation and harvesting processes. The festival's highlight is the grand tasting event, where local chocolatiers and pastry chefs present various chocolate-infused creations, from truffles to savory dishes. Live music and hula performances add to the festive atmosphere, making it a sensory delight. The festival also emphasizes sustainability and supports local cacao farmers, with proceeds contributing to the growth and development of the industry. 

When: May 9th

Where: Hilo Hawaiian Hotel, Hilo

Big Island Film Festival

Cinephiles will be drawn to the Big Island Film Festival, an annual celebration of independent filmmaking set against the picturesque backdrop of Waikoloa. This five-day event showcases a curated selection of narrative films from around the globe, emphasizing storytelling that resonates with authenticity and creativity. Screenings are held outdoors, allowing attendees to enjoy movies under the starlit Hawaiian sky. Beyond film viewings, the festival offers workshops and panel discussions led by industry professionals, providing insights into various aspects of filmmaking, from scriptwriting to production. Networking events and social gatherings foster connections among filmmakers, actors, and enthusiasts, creating a collaborative and inspiring environment. The festival culminates with the Golden Honu Awards, honoring standout films and performances and solidifying its reputation as a platform for emerging talent in the cinematic arts.

When: May 22–26, 2026

Where: Waikoloa

Big Island Jazz & Blues Festival

Music aficionados will not want to miss the 13th Annual Big Island Jazz & Blues Festival. This premier event brings together Grammy Award-winning artists, jazz legends, and blues greats for an unforgettable evening of performances. The 2026 festival is confirmed for May 14–17, with the Main Festival Concert on Saturday, May 16th. Set on the oceanfront grounds of the Mauna Kea Beach Hotel, the festival offers a serene and intimate setting where the soothing sounds of jazz and the soulful rhythms of blues harmonize with the gentle lapping of ocean waves. Attendees can expect a lineup of internationally acclaimed musicians, each bringing their unique flair and mastery to the stage. The festival highlights musical excellence and embodies the spirit of aloha, fostering a sense of community and shared appreciation for the arts. With gates opening in the late afternoon, guests can enjoy the sunset as a prelude to the evening's performances, making for a truly enchanting experience.

When: May 16th

Where: Mauna Kea Beach Hotel, Kohala Coast

More Info: Jazz & Blues

May on the Big Island of Hawaii is a month rich with cultural festivities and community gatherings that highlight the island's unique heritage and artistic vibrancy.