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‘Iole is home to breathtaking hiking and walking trails, as well as relaxing picnic areas, accessible by permission 8am-4pm daily. Check in with ‘Iole staff upon your arrival to sign in and receive a trail map as well as information about trail conditions and closures.
Trails include:
Waianaia Gulch Trail
2+ miles
Head toward the Waianaia Gulch trail by traveling eastward across Hawai’i's largest organic macadamia nut orchard. When you reach the gulch, arrows will point north or makai (toward the ocean) as the trail descends on an old grassy road, parallel to the gulch. At the bottom of the hill, the trail crosses Waianaia’s seasonal streambed and ascends mauka (uphill) through the lush and wild ravine. Finally the trail emerges from the gulch and heads north or makai (downhill) again for a short distance before returning west through the mac nut trees and toward the Bond Homestead.
Bond Forest Trail
Approximately 1 mile
THIS TRAIL IS CLOSED EACH SUNDAY
At top of the Upland Loop Trail, the Bond Forest trail commences, running through the whispering ironwood and fragrant eucalyptus trees of the Bond Forest. Along the pine-needle covered forest pathway, hear the call of the ‘Io (Hawaiian Hawk) as it soars through the sky or perches watchfully in tree branches. Follow the trail-marker ribbons through the forest and then, finally, back into the macadamia nut orchard. The Bond Forrest trail concludes by returning to top of the Upland Loop.
Upland Loop Trail
3 miles
THIS TRAIL IS CLOSED EACH SUNDAY
The Upland Loop trail follows old sugar cane roads up the steady elevation of ‘Iole ahupua’a. Pass through the pedestrian gate at the top of ‘Iole Road and follow trail markers, bearing east for a hundred yards, then south along a row of Norfolk Island Pines. Continue mauka (uphill) through the organic orchards, taking in views of Maui and the Kohala coastline. Pass the trees of Bond Forest and follow Upland Loop trail markers, heading west over the road and through ironwood trees. Finally, turn north or makai (toward the ocean), and follow the road back to top of ‘Iole Road.
Pali Akamoa Gulch Trail
1.2 miles
A short “wilderness” hike with brief steep elevations as it enters and exits the Pali Akamoa Gulch, this trail starts out under a canopy of banyan trees, heading mauka (uphill) toward Kalahikiola Church, originally built with stone by Father Elias Bond in 1855. From the church, the trail turns west and then descends into the gulch and meanders downhill through dense vegetation along a dry streambed area. Finally, the trail emerges from the gulch near the Historic Bond Homestead, where buildings and gardens date back to 1841.
Portuguese Oven Loop
Approximately 1 mile
Near the end of the Pali Akamoa trail, an additional loop travels north or makai (toward the sea) and back, allowing for a glimpse of old Portuguese bread-baking ovens, which are now cracked by the roots of fast-growing banyan trees. The Portuguese arrived in the islands during the later part of the 1870s as workers for Hawai’i's sugar cane plantations, bringing with them the method of baking bread in wood-burning ovens.




