Big Island Events in September 2026

Events & Festivals on the Big Island of Hawaii

06-06-2026

Tori C. Derrick

President & certified Hawaii travel expert with 15+ years of experience in Hawaii tourism.

2026 Events and Festivities

September on the Big Island has two big planning anchors. Labor Day weekend belongs to the Queen Liliʻuokalani Canoe Race in Kailua-Kona. Mid-September belongs to Waimea for Paniolo Festival Week. Both now have official 2026 dates posted, so check lodging and rental-car availability before you finalize flights.

A cultural festival on the Big Island of Hawaii

Queen Liliʻuokalani Canoe Race

Held over Labor Day weekend, this is billed by organizers as the world's largest outrigger canoe race — several days of paddling in Kailua-Kona honoring Hawaiʻi's last reigning monarch. If you're staying Kona-side, treat the race as a real travel factor. Waterfront rooms, restaurant tables, and rental cars all get tight once crews and families arrive. Our Queen Liliʻuokalani Canoe Race visitor guide covers the spectator side in more detail.

When: September 3-7, 2026 (Labor Day weekend)

Where: Kailua-Kona (Kona side)

More Info: qlcanoerace.com

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Paniolo Festival Week & Waimea Paniolo Parade

The Big Island's flagship Aloha Festivals event runs a full week in Waimea in September. The Saturday parade brings pāʻū riders, floats, equestrian units, and community groups through town before the day continues with a hoʻolauleʻa at Kalani Schutte Waimea District Park. The official 2026 festival page lists Paniolo Festival Week for September 14-19, with the parade on Saturday, September 19. If the parade weekend matters to you, this is the reason to plan a Waimea day into your itinerary.

When: September 14-19, 2026; parade on Saturday, September 19

Where: Waimea (Kamuela)

More Info: Aloha Festivals Island of Hawaiʻi

Hawaiʻi Kūpuna Hula Festival

One of the island's quieter cultural events. Kūpuna (elders) perform hula at the Outrigger Kona Resort & Spa in Kailua-Kona, often paired with a daytime craft fair. Hawaiʻi County Parks & Recreation now lists the 2026 festival for September 9-10, so this is a midweek cultural option if you are already staying on the Kona side after Labor Day weekend.

When: September 9-10, 2026

Where: Kailua-Kona

More Info: Hawaiʻi County Parks & Recreation

Anaehoʻomalu Bay on the Big Island's Kohala Coast

Labor Day (Federal Holiday)

Labor Day falls on Monday, September 7 in 2026, and the long weekend is the busiest stretch of the Big Island's September calendar. Expect heavy demand around Kailua-Kona for the canoe race, and check Waimea road and parking conditions if the rodeo schedule overlaps your plans.

When: Monday, September 7, 2026

Where: Statewide

Pick your anchor first. Kona over Labor Day if you want paddling energy and waterfront crowds. Waimea for the Paniolo parade if the cultural celebration is the point of the trip. A couple of things readers ask about that aren't September options: the Hawaiʻi County Fair in Hilo hasn't been held since 2019, and the Kona Coffee Cultural Festival is a November event, not a September one.

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