It’s May in the islands of aloha — here’s what not to miss!
Go for a long scenic walk, enjoy chef-made food and entertainment afterwards and help dozens of island nonprofits by doing so: That’s the premise of the Visitor Industry Charity Walk, which takes place May 3 on Oahu and Kauai and May 20 on Maui and Hawaii Island. Since 1978, the walks have helped raise nearly $50 million for local charities, many of whom provide aid and children’s activities along the way. Hotel and tourism employees, meanwhile, spend months fundraising and planning the day’s festivities. New this year to the Oahu walk is the addition of the 1-kilometer, ADA-friendly Laulima Loop, designed for those not up for the standard 4.5-mile route that starts at Ala Moana Beach Park’s Magic Island.
Feature photo courtesy of Honoka’a Western Week on Facebook.
Oahu
The many islands of Micronesia share significant cultural ties with Polynesia as well as distinctive traditions of their own. Immigrants from the Gilbert Islands introduced grass skirts to Hawaii’s hula dancers, who still traditionally wear ti leaves, in the late 19th century, while Micronesian navigator Mau Piailug helped restore the Hawaiian heritage of ocean voyaging by sharing his wayfinding skills in the mid-1970s. The Bishop Museum’s Celebrate Micronesia festival on May 3 is a great place to learn more about the region with weaving, cultural performances, food vendors, art and craft displays/sales and hands-on demonstrations.
Here are highlights of events around Oahu in May:

May 1
May 1 is Lei Day throughout Hawaii, but Oahu observes it with more flair and fragrant flowers, capped by the May Day is Lei Day event that evening at the Tom Moffat Waikiki Shell. In addition to performances by hula schools and musicians including ukulele players and Hawaiian reggae artists, the open-air venue will offer food, family activities and lei-making competitions.
May 26
The annual Shinnyo Floating Lantern Hawaii ceremony at Ala Moana Beach Park provides a poignant opportunity to remember lost loved ones by writing their name on special paper and wood lanterns that are set adrift at sunset, following a short program of Hawaiian chant, music and Shinnyo Buddhist rituals. There’s no charge for the lanterns, which are collected later to prevent ocean pollution, but arrive early to obtain one, or submit a name online to be added to one of the “Collective Remembrance” lanterns.
May 10
A benefit for the Kapiolani Medical Center for Women and Children, the annual Ko Olina Children’s Festival brings five hours of kids’ activities and entertainment to the Great Lawn of Ulua Lagoon — No. 4 of Ko Olina’s protected lagoons with sandy beaches. Vendors will offer food and drink, while the nearby Four Seasons Resort Oahu and Disney’s Aulani resort have special room rates for ticket holders.
Maui
The Maui Nui Visitor Industry Charity Walk on May 10 is pretty short: just 2.5 miles, starting and ending at the War Memorial Special Events Arena in Wailuku. That means you get an early start on enjoying the free breakfast, live entertainment and prize drawings after your walk, while still raising plenty of funds for local nonprofits — $1.4 million went to 64 charities in Maui County (which includes Lanai and Molokai) last year.
Here’s what else to watch or nosh on the Valley Isle this month:

Every Monday and Wednesday afternoon
Take a free, 1-mile walking tour of Kihei every Monday and Wednesday afternoon with Historic Maui Walking Tours, whose guides share stories of the community’s Hawaiian heritage and the modern influence of the U.S. military and tourism. Make a reservation to claim one of 25 spots on the tours, which start at Kihei Public Library and end in time to watch the sun set over the ocean.
May 17
Raise a glass or two to the Maui Arts & Cultural Center in Kahului at its annual fundraiser, the Maui Brewers Festival on May 17. Open to ages 21 and older, the event includes craft beer tasting, complimentary food from island chefs, live music and — for the nondrinkers — local cold brew coffee, kombucha and Maui Brewing Co. root beer.
May 3
The Hyatt Regency Maui Resort & Spa in Kaanapali marks its 45th anniversary with an ‘Aha Mele (concert) May 3 on its Halona Kai Law, featuring acoustic music by local artist Akoni and headliner Anuhea, plus food, drinks and arts and crafts for sale. A portion of the proceeds will benefit Maui’s Visitor Industry Charity Walk.
Hawaii Island
Most of Hawaii’s plantation-era immigrants came from the east, but one large group headed west: the Portuguese, primarily from the Azores and Madeira. They brought sweet bread, sausages and malasadas (doughnuts) that have become staples of island cuisine, part of their legacy that their descendants celebrate at the annual Holy Ghost Festival (June 8 this year). Portuguese Heritage Night at the Honoka’a Heritage Center on May 15 will offer samples of the traditional foods, insights into Holy Ghost Festival traditions and prize drawings.
Here are more highlights for May on Hawaii Island:

May 11
Mother’s Day inspires the music at the annual spring concert of the Kona Choral Society & Orchestra on May 11 at the Kaleiopapa Convention Center at the Outrigger Kona Resort & Spa in Keauhou. The program features maternal-themed selections such as “Garten Mother’s Lullaby” and “The Softness of My Mother’s Hands,” plus “Kona Kai Opua,” “A Little Jazz Mass” and “Hawaii Island Suite.”
May 17–26
Honoka’a Western Week honors the paniolo (cowboy) heritage of the region May 17–26. Festivities begin with a parade, block party, talent show and country dancing May 17 and end with a rodeo May 25–26, with lots of free, family-oriented events in between.
May 31
The Ironman 70.3 Hawaii, better known to veteran triathletes as the Honu Half Ironman, turns 20 this year, with an after-race party to give competitors another reason to cross the finish line on May 31. The race starts and ends at the Fairmont Orchid, including a 1.2-mile ocean swim, a 56-mile bike ride to Hawi and back and a run on pavement and golf greens on the Mauna Lani Resort.
Kauai
May brings drier weather to the North Shore, meaning better but still rugged conditions along the Napali Coast’s renowned Kalalau Trail. Make reservations early to access the trailhead and parking or the shuttle from Hanalei or Princeville. If you plan on going past Hanakapiai Beach, about 2 miles in, you’ll also need to apply for a state camping permit. Only 80 permits are issued per day, available online up to 90 days in advance and by walk-in at the state parks office in Lihue up to 30 days in advance.
Here are other fun events on Kauai this month:

May 3
Cinco de Mayo inspires the Tres de Mayo salsa music dance party May 3 in Kilauea. Kauai’s seven-man Pico de Gallo band serves up salsa, cumbia and other dance music at the Porter Pavilion in Anaina Hou Community Park, with food and drink available. Go early to enjoy Kauai’s only mini golf course or a drink at the Sunset Lanai.
May 10
The descendants of Okinawan immigrants who first arrived in Hawaii in 1900 have maintained their distinctive culture, as you can discover at the Kauai Okinawan Festival, May 10 at Kukui Grove Center. Listen to sanshin music and taiko drums, watch Eisa Bon dancers, participate in a mini-Japanese Bon ring dance and enjoy traditional treats like andagi (doughnuts).
May 25
Cyclists who want to race uphill amid some of Kauai’s most spectacular views should sign up for Pedal to the Meadow on May 25. The nearly 15.75-mile-long climb starts at sea level in Kekaha and winds its way past Waimea Canyon overlooks and through the forest to Kanaloahuluhulu Meadow in Kokee State Park, deliciously cooler at an elevation of 3,835 feet.