Things to Do on O‘ahu in September 2023
Treat yourself to an evening of dishes from Hale ‘Aina award-winning restaurants, go to a block party in Waikīkī and sign up for Hawai‘i’s largest cycling event.

Photo: Courtesy of the Ritz-Carlton Residences, Waikīkī Beach
FOOD & DRINK
2023 Hale ‘Aina Awards Celebration
Sept. 9, 6–9 p.m.
Join us for an unforgettable evening at HONOLULU Magazine’s 40th Hale ‘Aina Awards Celebration. Don’t miss your chance to indulge in some of the best food from this year’s winners, all in one place. The theme for 2023 is Whimsical Wonderland, so come dressed to impress. 10% of ticket sales will be donated to the Hawai‘i Community Foundation’s Maui Strong Fund.
$150–$225, Hawai‘i State Art Museum, hnltix.com, @honolulumag
SEE ALSO: HONOLULU’s Biggest Foodie Event is Back

Photo: Asiavision/E+ via Getty Images
FESTIVAL
Festa Italiana
Sept. 15 (VIP) and 16 (street festival)
Hawai‘i’s only Italian festival returns for the first time since 2019, bringing together local vendors to serve up everything from pizza, pasta and wine to cheese, bread and gelato. The festival will also showcase Italian music and art and a selection of luxury Italian cars provided by Velocity Honolulu. This year’s street festival is free, though you can purchase VIP tickets for an additional event at Velocity Honolulu.
Free admission, Kaka‘ako, festaitalianahawaii.com, @festaitaliana
FAST FACT: On Sept. 30, Aloha Festivals will host the 75th Annual Floral Parade in Waikīkī.

Photo: Courtesy of Hawai‘i Bicycling League
SPORTS
40th Annual Honolulu Century Ride
Sept. 24, 5 a.m.–5 p.m.
Bicyclists of all ages and skill levels are welcome at Hawai‘i’s largest cycling event. You can choose your riding distance in 25-mile increments or go the full distance of 100 miles, from town all the way to Ka‘a‘awa on the Windward Side and back. When you’re done, there’ll be food and music waiting for you where you started at Kapi‘olani Park.
$25–$80, Kapi‘olani Park, hbl.org, @hblridealoha

Photo: Courtesy of Maui Ola
CONCERT
Kolohe Kai Summer Tour
Sept. 29, 6:30–10 p.m.
One of Hawai‘i’s most streamed reggae artists of the past decade, Kolohe Kai, will be performing at the Waikīkī Shell, inviting you to “Feel the Sunshine” and “Cool Down.” Joining the lineup will be reggae singer Matisyahu and alternative band Cydeways.
$29.50–$89.50, Waikīkī Shell, blaisdellcenter.com, @kolohekaimusic
SHOPPING
Neiman Marcus Honolulu 25th Anniversary Celebration
Sept. 8–9, 11 a.m.–7 p.m.; Sept. 10, noon–4 p.m.; Sept. 15–18, various times
The luxury retailer celebrates its silver anniversary with various festivities. Take in a Sogetsu ikebana exhibition Sept. 8–10. Then, from Sept. 15–18, enjoy trunk shows, designer appearances and special anniversary products and savor daily treats, including an exclusive Asato Family Shop ice cream flavor.
Neiman Marcus, Ala Moana Center, neimanmarcus.com, @neimanmarcushawaii
FESTIVAL
69th Annual Waikīkī Ho‘olaule‘a
Sept. 23, 6–9:30 p.m.
Get ready for Hawai‘i’s largest block party, a beachfront street event hosted by Aloha Festivals. Kalākaua Avenue will be filled with booths with local foods and crafts. Entertainment on multiple stages will keep the party going, with performances from local artists, hālau hula and more.
Free admission, Waikīkī, alohafestivals.com, @alohafestivals
SEE ALSO: Our Guide: Honolulu Summer Festivals
FILMS
Honolulu Rainbow Film Festival
Sept. 8–10 in person, Sept. 11–18 online
Doris Duke Theatre Founded by the Honolulu Gay & Lesbian Cultural Foundation, the Honolulu Rainbow Film Festival will showcase several films that educate and raise awareness of the gay and lesbian culture, arts, lifestyle and community.
SEE ALSO: Honolulu’s LGBTQ+ Film Festival Returns