Every time there’s a holiday in Hawaii I try to take complete advantage of outdoors. This MLK day my friend Courtney and I decided to tackle the Tom Tom trail on the east side of the island. The trail is about 6.6 miles from Makapuu to Waimanalo and about 3-4 to and from the Tom Tom Trail Puka. We decided to do the entire 6.6 mile route.
How to get to Tom Tom Trail
Begin from the ever popular Makapuu Lookout- near the Makapuu Tide Pools hike. From there, cross the street and head up the hill along side of the fence that says ‘No Hiking’ (Sorry, Mom!). The fence will end at the top of the hill and you make a right along the cliff edge for some fantastic costal views of Makapu’u.
DISCLAIMER: If you decide to hike the entire trail you will either need one car at Waimanalo (park at the 7/11) and one car at Makapu’u Lookout. Or you can uber/hitchhike back to the begining–just be careful and be smart!
What to Expect from the Tom Tom Trail
The first 15 minutes or so on the trail is a lot of up-hill climbing but it offers the most fantastic views. There are multiple jetted rocks that make great photo opps–but be careful if you venture out on one as some of the rocks aren’t stable.
About an hour into the hike you’ll come to a set of rock formations where you will find the Tom Tom Puka. This is another picturesque spot with views of Rabbit Island and the Makai Research Pier. You can climb through the puka or on top for a great birds eye view.
At this point you can turn around and go back the way you came, or you can continue on for the next 4-5 hours until you reach Waimanalo. We decided to continue onward.
Past the puka is another mountain with a slightly overgrown path. As long as you stay along the cliff edge you won’t get lost.
After this mountain you will come across an old launching pad for paragliding. This is another opportune spot for pictures. Shortly after the first launching pad you come to The Dead Man’s Cat Walk. This hike is now illegal and prior to the hike I was completely unaware that we were going to end up there.
Now this is sketchy because you are trespassing and there’s usually people working on the mountain so you have to be very careful.
From the second launch pad there’s a path that leads to a paved access road. Go down the access road until you get to a gate that says ‘No Trespassing’. On the right side are concrete stairs. Follow those down the path and follow along the gate. When you get to the gates edge go around it and follow the path up and over the rocks. The trail is extremely overgrown but once you pass the cell phone towers you’ll come to another hill which opens up to a more clear trail opening.
This section of the trail has a steep rock incline and you will find a couple ropes and cables along the descent. The trail becomes narrow and another rock climb led us to a shady pine area with incredible views of Waimanalo. Continue on with this trail and follow the Koolau Summit Trail. There is a junction and you will want to keep to the right. Again, remember to stay on the cliffs edge and you won’t get lost.
At the peak of this trail we found a young woman in a lounge trail reading a book. Apparently her boyfriend was a helicopter pilot who was working on the satellites on the ridge and dropped her off at the top peak to sunbath. Courtney and I found this to be wildly entertaining and a nice break opportunity.
Continue on the trail and follow the pink ribbons (not orange) until you find yourself on a peak with giant electric poles. You will see a path down to the right marked with the pink ribbons. The descent is rocky but nothing too crazy.
Once you enter a wooded area you are about 15 minutes from the end of the trail. You will end up at a dead end of Waiokeola Road. From here just make your way back to your second car in Waimanalo or call an uber to get back to your starting point.
I would recommend this hike to advanced hikers as the trails have overgrown and the rock climbing can be intense at some points. Again, part of this trail is completely illegal so if you’re worried about getting a ticket then look into other hikes or activities in my Oahu Guide.
Hope everyone enjoyed and feel free to comment with any questions! Mahalo