President & certified Hawaii travel expert with 15+ years of experience in Hawaii tourism.
We may earn a commission when you book or buy through links on this page.
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.
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.
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
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
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.
Mostly dry and breezy across Oʻahu today through Monday, with northeast winds holding steady and only light showers popping up on windward slopes. Leeward and resort areas stay dry.
Late Tuesday the pattern shifts. Winds drop and turn southerly, and tropical moisture moves in Wednesday through Friday—heavy rain will hit the islands, with potential flash flood conditions. Timing and intensity are still uncertain, but plan on wet weather. Ocean conditions will be choppy and elevated through Monday, then gradually ease midweek.
Hit the leeward beaches and snorkel sites Monday and Tuesday. Save indoor plans for Wednesday through Friday.
0:000:56
Voice
Read the transcript
Steady northeast winds and mostly dry skies today through Monday. Light showers may pop up on windward slopes and in the mountains, but leeward and resort areas stay mostly dry.
Late Tuesday the pattern shifts. Winds drop and turn southerly, then deep tropical moisture moves in Wednesday through Friday. Heavy rain is likely statewide from late Wednesday onward, with potential flash flood conditions—timing and intensity are still uncertain. Ocean conditions are rough and choppy through Monday on windward shores due to strong winds, then gradually ease mid-week. A slightly larger northwest swell peaks Wednesday, and a west swell from a distant typhoon may bring moderate surf to west-facing Big Island shores by Thursday.
Leeward beaches and snorkeling work well Monday and Tuesday. Save indoor plans for Wednesday through Friday.
0:000:52
Voice
Read the transcript
Steady northeast winds and mostly dry skies today through Monday, with only light showers scattered across windward slopes and the mountains. Leeward and resort areas stay dry. Ocean conditions are rough and choppy—a Small Craft Advisory is in effect through Monday evening.
Late Tuesday brings a shift. Winds drop and turn southerly, and tropical moisture moves in Wednesday through Friday. Plan for heavy rain and potential flash flooding from late Wednesday onward. Timing and intensity are still uncertain. Surf will ease mid-week, though a northwest swell peaks Wednesday and a distant typhoon may send moderate west swell to west-facing shores by Thursday.
Leeward beaches are your play Monday and Tuesday. Plan indoor activities starting Wednesday when the rain arrives.
0:000:50
Voice
Read the transcript
Steady northeast winds are pushing cool, dry air across Kauaʻi right now. Light showers will pop up mainly on windward slopes and mountains through Monday, but leeward and resort areas stay mostly dry.
A pattern shift arrives late Tuesday. Winds will drop and turn southerly, and deep tropical moisture will move in Wednesday through Friday. Heavy rain is likely statewide from late Wednesday onward, with potential flash flood conditions—timing and intensity details are still uncertain. Surf will be choppy and elevated through Monday due to strong winds, then gradually ease mid-week before a slightly larger northwest swell peaks Wednesday.
Leeward beaches and snorkeling are best Monday and Tuesday. Plan indoor activities for Wednesday through Friday.
Created with AI from the official NWS forecast discussion · verify with NWS before heading out
Created with AI from this HawaiiGuide page and read by a computer-generated voice. Double-check fees, hours, and reservations on the full page before you head out. Hawaiian pronunciation is tricky for synthesized speech and a few words may land slightly off; mahalo for your patience as we keep refining.
Mele and Kani are computer-generated voice options chosen for clarity and warmth.
Get Your Free Hawaii Visitor Guide
Enter your email and we'll send you instant access to our free 2026 Hawaii Starter Guide + Summary Guidesheets.