Our trail is experiencing the same problems as many other O‘ahu hiking trails; it is being loved to death. Though located on state land, this trail is not on the managed inventory of DLNR’s Na Ala Hele and Access Program.
The Ka’iwa Ridge Trail, otherwise known as the Pillbox Trail, is located on the ridge overlooking Lanikai and Enchanted Lakes, both suburbs of Kailua on the windward side of Oahu. Lanikai was once an agricultural area with fields of watermelon, but later the area became secluded weekend vacation homesteads for the wealthy to escape from Honolulu. The beauty of Lanikai beach and Lanikai Bay with it’s close proximity to the Mokulua offshore islands has turned Lanikai into a world class destination. The trail has become one of the most popular on the island because of the stunning views of Kailua Bay, the Ko’olau Mountains, ease of accessibility, and length of hike. A recent survey showed 1,500 visitors in one day, second only to Diamond Head.
The “pillbox trail” may be accessed by either of two public easements over private property (even though they are not yet managed for public use. Other accesses are subject to landowner approval, and if used without authorization, you will be trespassing and putting yourself at risk). The entrance originating in Enchanted Lakes is at the end of Kamahele Street, and the most popular one originates on the Lanikai side of the Bluestone property. If you branch off from the main trail you will probably end up on private property.
The entrance to the Lanikai side of the trail is very worn, and ropes are needed to get up the first part because of severe erosion due to the onslaught of hikers in recent years.
Although it may look like fun, the boulders are not always stable and may give way at any time. It may be a good photo op but why take chances?
There are lots of bicycle shops in Kailua where you can rent a bike if you take the bus to Kailua.