Hawaii’s beaches are reason enough to plan a trip, but the fall calendar gives travelers another way into the islands. On Oahu and Maui, October and early November bring a mix of performing arts, community celebration and food events. Here are four dates to build a getaway around in 2026.
October 3: Dinner and ballet at Ko Olina, Oahu
At Four Seasons Resort Oahu at Ko Olina, the Italian restaurant Noe will host An Evening of Flavor and Dance on October 3. The five-course dinner pairs each stage of the meal with performances by Ballet Hawaii dancers, bringing the company into the restaurant’s garden setting rather than placing the audience in a theater. Wine pairings are part of the evening, and a portion of the proceeds will support Ballet Hawaii. The event begins at 5 p.m.
For travelers staying in Waikiki, Ko Olina is on Oahu’s leeward coast, making the dinner an occasion to spend more time on the island beyond Honolulu.
October 14–18: Honolulu Pride in Waikiki, Oahu
Honolulu Pride fills several days in October, with its parade and festival scheduled for Saturday, October 17. Waikiki makes a natural base for visitors who want to join the celebration and spend the rest of the trip close to the beach.
Two hotels highlighted in the announcement are ʻAlohilani Resort Waikiki Beach, which plans Pride programming at its SWELL pool deck, and The Twin Fin, a beachfront property along the parade route. ʻAlohilani’s planned LEI Pool Party includes entertainment and themed cocktails; check the resort’s current calendar for the party’s confirmed date and entry details. Beyond the hotel events, the official Pride schedule is the best place to plan around the parade and other community gatherings.
October 25: A beachfront brunch in Kāʻanapali, Maui
The Hawaiʻi Food & Wine Festival comes to Royal Lahaina Resort & Bungalows on October 25 for No EGGScuses, Let’s Brunch! The walk-around event brings six chefs to Kāʻanapali Beach for dishes built around the egg, from familiar brunch preparations to more inventive uses of roe and local ingredients. Cocktails and other drinks round out the afternoon.
The brunch runs from 11 a.m. to 1 p.m. It is an outdoor event for guests ages 21 and older, so families traveling with children will need a different plan for that part of the day.
November 6: Festival cocktails in Waikiki, Oahu
Back on Oahu, ʻAlohilani Resort Waikiki Beach hosts 24K Magic on November 6. The Hawaiʻi Food & Wine Festival’s rooftop cocktail tasting brings together mixologists, chefs and island flavors at the Waikiki resort. It runs from 6 to 9 p.m. and is open to guests ages 21 and older.
The broader festival runs from October 16 through November 8, with events across multiple islands. If your travel dates do not line up with the Maui brunch or Waikiki tasting, check the full festival schedule for another stop that fits your itinerary. Event plans can change, so confirm the latest details with organizers before heading out.
