Located in the charming city of Kailua, Hawaii, the Kalaheo Hillside Trail has been gaining traction among both novice and experienced mountain bikers. Offering a versatile singletrack and scenic views of the Mokes and the famed Lanikai Beach, this trail is a delightful mix of ease and excitement. Locally maintained and ever-evolving, this is a cycling spot you wouldn't want to miss.
Once you arrive in Kailua, head toward Kalaheo High School. After climbing a small hill, make a right onto Iliaina St., facing the hillside. Keep going until you encounter a driveway-sized ramp that is chained off. A dirt and gravel path leads the way, and a clearing in the tall grass marks the trail's entrance.
The Kalaheo Hillside Trail is particularly appealing for its flexibility. For those who love straightforward rides, sticking to the main singletrack offers an uncomplicated yet engaging experience. If you're looking for more, the loop that winds up the hill adds some twists and turns to the adventure.
About a quarter of the way into the trail, a side path can quickly take you to the hilltop. It’s a wonderful option for those eager to reach elevated vantage points sooner.
For those up to the challenge, the trail also includes a more complex backside. This section is a step up from the one-mile pump track located at the trailhead, featuring more demanding jumps.
Kudos to the local community for their excellent maintenance of the trail. While riding, you'll notice cans, bottles, and gardening tools neatly placed along the sides of the trailhead, adding a quirky yet functional aspect. This care ensures the trail stays well-groomed while also providing a bumpy, fun terrain.
In a tucked-away corner of the trail network, beginners can find a dedicated pump track to hone their skills. It's a great place to get more comfortable before tackling more challenging terrains.
Don't forget to take in the splendid views of the Mokes and Lanikai Beach, which make the ride even more rewarding.
Kalaheo Hillside Trail offers something for everyone—whether you're a beginner looking to gain experience or a seasoned cyclist seeking a laid-back yet exhilarating ride. With its well-maintained network of paths and the scenic beauty of Kailua, this trail comes highly recommended for anyone looking to explore Hawaii's cycling landscape.
10 mi 
