On the last Sunday of September, thousands of cyclists roll out of Kapiʻolani Park before sunrise, point their handlebars toward the windward coast, and spend the morning riding past Diamond Head, Hanauma Bay, Makapuʻu, and the Koʻolau cliffs. The Honolulu Century Ride is the Hawaii Bicycling League’s biggest fundraiser and, per HBL, Hawaiʻi’s largest cycling event. If you’re booking a trip three months out, here’s what’s actually involved — whether you’re riding, spectating, or just trying to avoid the road closures.

The 2026 event is scheduled for Sunday, September 27. HBL has registration open from its official ride page, with pricing tiers and event-weekend options posted there. If you’re thinking about riding, this is the window to commit before late-summer demand tightens bike rentals, hotel blocks, and flight choices.

The Honolulu Century Ride is not a race. It’s an untimed, supported ride with multiple distance options that share the same start, the same first stretch of coast, and the same finish-line atmosphere back at Kapiʻolani Park. Riders pick a distance based on fitness and ambition, ride at their own pace, and turn around at one of several aid stations along the route.

HBL uses the ride to fund advocacy and education work, including its BikeEd Hawaiʻi program for fourth graders on Oʻahu. So the entry fee is doing two jobs: putting you on a supported ride with aid stations and course help, and funding the people pushing for safer streets across Hawaiʻi.

HBL’s 2026 ride page lists four distance options that all start at Kapiʻolani Park and head east. The out-and-back course runs from Waikīkī through the south shore and windward side toward Swanzy Beach Park in Kaʻaʻawa, with official RideWithGPS maps linked from the course information tab. Use HBL’s current route files for exact turnarounds before you train or book support.

• 25-mile out-and-back — turns around at Sandy Beach Park, the first aid station and the best visitor option if you want the Kaiwi Coast scenery without a full-day ride.
• 50-mile — pushes deeper into the windward side before turning back toward town.
• 75-mile — adds more windward riding and has earlier course cutoffs than the shorter options.
• 100-mile option — continues toward Swanzy Beach Park in Kaʻaʻawa before returning to Kapiʻolani Park.

The geography is what makes this ride. You climb out of Waikīkī past Diamond Head, drop into the cliffside section above Hanauma Bay and Halona Blowhole, round Makapuʻu Point with the windward beaches spreading out below you, and then ride the coastal stretch through Waimānalo with the Koʻolau cliffs on your left and the ocean on your right. Per the official HBL course info, the Kaiwi Coast section from Hanauma Bay to Sandy Beach will be car-free from 6 a.m. to 8 a.m. in 2026, and riders need to reach Lunalilo Home Road by 7:45 a.m. to use that closed-road window.

Visitors have two practical options: fly with your own bike, or rent on island. Flying with your own setup is doable, but confirm your airline’s current sports-equipment policy before you buy the ticket — oversized-bag rules change often and can depend on box size, weight, and fare type. HBL’s 2026 ride page points visiting riders toward bike-transport resources including Aloha Air Cargo, BikeFlights, Hawaiian Airlines’ sports-equipment policy, and Roberts Hawaiʻi shuttle service for airport-to-hotel transfers with a bike.

Renting on Oʻahu is simpler, but do not leave it for arrival week. Confirm current rental options before you fly, and reserve well ahead for century weekend — inventory is the obvious bottleneck, especially for performance road bikes in common sizes.

Whichever you pick, build in a shakedown day before the ride. Adjust the saddle, dial in shifting, and ride a quick loop around Kapiʻolani Park or out to Diamond Head so you discover any problems before mile 30 of a strange coastline.

Plan to be in Kapiʻolani Park well before sunrise and confirm the final start schedule on the official ride page before you fly. Riders leave in pace groups rather than all at once, which spreads the field before the route leaves Waikīkī.

Late September on Oʻahu typically runs warm and humid, with steady trade winds and the occasional brief windward shower — check the forecast in the days before you fly. HBL calls the route mostly flat but notes that the prevailing east or northeast wind can be more challenging than the hills. Pace the return from Waimānalo and Kailua accordingly.

The finish is one of the friendlier scenes in Hawaiʻi cycling. Riders stretch on the grass at Kapiʻolani Park, food vendors set up under the trees, and the HBL volunteers — who built the whole thing — actually look like they’re enjoying themselves.

You don’t need to ride to enjoy the day. Kapiʻolani Park is open during the event — bring coffee and watch the start, then come back midday to cheer riders into the finish. Halona Blowhole Lookout, Makapuʻu Lookout, and the Lānikaʻi/Waimanalo overlooks are good roadside vantage points for the longer distances rolling past.

Two practical notes if you’re driving on Oʻahu that morning: expect delays on Diamond Head Road, Kalanianaʻole Highway between Hawaiʻi Kai and Waimānalo, and stretches of Kamehameha Highway up the windward coast. HBL says Kalanianaʻole Highway will close from Hanauma Bay to the entrance of Sandy Beach Park from 6 a.m. to 8 a.m. for the outbound Kaiwi Coast segment; other roads on the course remain open to vehicles. If your itinerary includes Hanauma Bay or the windward beaches that morning, build in extra time or shift to the afternoon.

Late September is a solid window for visiting Hawaiʻi. Summer crowds have thinned, school is back in session on the mainland, and hotel rates often ease up after the Labor Day cutoff — see our post-Labor Day Hawaii hotel rates guide for the pattern we typically see. HBL also lists 2026 participant hotel offers near Waikīkī, but confirm current codes and terms on the official ride page before booking around them.

Pair the ride with a few easy add-ons: a Diamond Head sunrise hike on a non-ride day, a snorkel session at Hanauma Bay (book through the City and County of Honolulu’s reservation system, which opens reservations two days in advance starting at 7 a.m. HST), or an Aloha Festivals event — the month-long celebration runs through September and frequently has Waikīkī events landing on the ride weekend.

For rental cars, Discount Hawaii Car Rental is a practical way to compare quotes if you need a vehicle for bike transport or for non-ride days. And browse Oʻahu hotels if you haven’t booked yet — Waikīkī puts you within riding distance of the start line, which beats driving across town in the pre-dawn dark.

The Honolulu Century Ride isn’t the flashiest event on Hawaiʻi’s calendar, and that’s the appeal. It’s a local fundraiser that happens to put you on the Kaiwi Coast and the windward shoreline alongside a few thousand other people who showed up for the same reason. If your idea of a Hawaiʻi vacation includes earning the malasada at mile 60, this is the trip.