The 56th Annual Makawao Parade, to be held on June 29th at 9am in Makawao town, is a much-anticipated event each year. The parade kicks off a week of festivities filled with tradition, community spirit, and the vibrant culture of the Upcountry paniolo (cowboy) lifestyle. More than just a show, the parade demonstrates the town’s deep connection to its paniolo roots, blending its rich history with authentic experience for residents and visitors alike. “The parade, a much-treasured tradition, began decades ago as mounted units only,” said Maile J. Masada, the Director of Facility Operations for Oskie Rice Event Center. “Now, it includes floats, walking units, classic cars, marching bands, special tributes, and more.”

Cattle were first introduced to the islands in the 1790s, and ranching began to flourish in the mid-to-late 1800s. Mexican vaqueros (cowboys) helped Hawaiian ranchers as they learned to herd, breed, and slaughter cattle. During this time, a new Hawaiian cowboy or “paniolo” culture (originating from the Hawaiian pronunciation of “Español”) emerged as an integral part of Upcountry life.

The Makawao Parade and Stampede is a continuation of this history. Masada noted, “There is an event every day either in Makawao town or at the Oskie Arena after the parade, closing with the Makawao Stampede on the 4th of July weekend.” With spectators lining the streets, the parade route starts on Baldwin Avenue near the Veterans Cemetery, turns right onto Makawao Avenue, and ends on Makani Road near Kalama School.

This year’s Grand Marshal is paniolo Eugene DeRego. “Born and raised on Maui, DeRego grew up riding horses, competing in roping, motorcross, and drag racing, where he won many titles,” Masada explained. “There will also be a loving commemoration for special honoree Gladys Baisa, a cherished member of the Makawao community whose legacy continues to inspire.”

Following the parade, the Parade in the Country Concert will take place from 12-5pm at the Oskie Rice Event Center. There will be food, craft vendors, and an assortment of live entertainment including Jordan Soon Wai-Knot, Hālau Keʻala Kahinano O Puna, and Te Ohi Nui. Masada added, “Thanks to our many sponsors, we have set the stage for an unforgettable parade and holiday celebration!”