Textbooks down, boots laced up. As the school year kicks off and college students flock back to Oʻahu, the island isn’t just about lectures and late-night study sessions; it’s also a playground of over 100 trails waiting to be explored. From sky-high ridgelines to colorful pillbox lookouts and even a legendary staircase with a story of its own, Oʻahu serves up a hike for every mood and every type of adventurer. Here are six trails that should be at the top of your syllabus.
Stairway to Heaven (Haʻikū Stairs)
Stairway to Heaven is a very famous hike on Oʻahu, known for its beautiful views and the 3,922 metal stairs that make up the trail. It runs along the Koʻolau mountain range. There are two main ways to access the stairs. Many people mistakenly think the back route (Moanalua Middle Ridge Trail) is legal. No matter how you get there, once you step onto the stairs, it is illegal. From the back route, it is a 10-mile hike both ways. The front way to get to the stairs involved trespassing through a private neighborhood, but it is significantly shorter, cutting down the miles to just 2 miles round trip. The common misunderstanding is that this route doesn’t involve trespassing through a neighborhood; however, as soon as you set foot onto the stairs, it becomes trespassing. This hike was officially closed in 2002. Trespassing can result in a $5,000 fine, community service, or even jail time. Still, it remains a dream hike for many, and its reputation as a “must-do” (despite the risks) keeps it at the top of many hikers’ lists.
Mt. Olomana (Three Peaks)
Mt. Olomana, but more commonly known as Three Peaks, is located on the windward side near Kailua and Waimānalo. This hike is 4.5 miles out-and-back. The hike features three distinct peaks: Olomana, Pakuʻi, and Ahiki. Peak 1 is the easiest and most popular, but Peak 3 is recommended for more advanced hikers due to its steep drop-offs and exposed ridgelines. Take this hike seriously; between 2011 and 2022, six lives were lost on the hike, according to SFGATE. With an elevation gain of up to 1,856 feet, it is a unique hike because it is between the Koʻolau Mountain Range and the shoreline.
Pink Pillbox
The Pink Pillbox is on the shorter side of hikes compared to the others on the list. This legal hike takes 1–2 hours to complete. Short but sweet, perfect for a sunrise or sunset hike. Located on the Waiʻanae side of the island, it’s about 1.6 miles round trip with an elevation gain of 600–700 feet. The trail is dry and can get hot, which is common for this side of the island. The hike got its name from the pink painted pillbox, which is a World War II-era bunker at the top of the hike.
Pali Puka
This hike is slightly less popular than other iconic hikes listed here. It is located just off the Pali Lookout on the windward side. A very appealing aspect of this hike, especially for those who enjoy a rougher trail that gets straight to the point, is that it’s only 0.8 miles round trip. Some parts of the ridge become narrow and steep, with an elevation gain of 300–400 feet in just 20–45 minutes. I did it before sunrise once, and watching the island wake up from that height was unforgettable. Just use caution; the trail is short but exposed.
Stairway to Hell
Stairway to Hell is illegal and brutally tough as an alternative to Stairway to Heaven, just across the Moanalua Valley. This is a 10-mile trek with an elevation gain of over 2,800 feet. It can take 6–10 hours and includes rope climbs, narrow ridges, and constant elevation gain. It’s not for beginners, but with proper prep, it’s one of the most rewarding hikes on the island. The most important part of this hike is research, preparation, and watching the weather app for the perfect time to complete this hike. What to look for to know when it is the best time to hike here is low wind, clear sky, and no heavy rainfall. I have done this hike once with no intent of doing it again, but I am glad I did it.
Whether you’re in the mood for a quick sunset hike or a full-day adventure, Oʻahu has it all. Just be sure to respect the land, stay safe, and know your limits.