By Michelle Wohl
Mānoa Falls Trail. Photo by Sarah Burchard.
Oʻahu isn’t just about beaches and city lights, it’s also home to some of Hawaiʻi’s most stunning hikes. From easy walks with postcard views to demanding ridge climbs that test your endurance, the island has something for every traveler. Winter is a wonderful time to explore – the air is cooler and because it rains more in the winter, waterfalls often flow stronger. Here are seven of the best hikes for all fitness levels.
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Lēʻahi (Diamond Head Crater) Hike. Photo by Christian Mueller (Shutterstock).
Why go: The most popular hike on Oʻahu, Lēʻahi (also known as Diamond Head) rewards you with sweeping views of Waikīkī, Honolulu and the Pacific.
Trail details: 1.6 miles roundtrip, paved sections with some steep stairs at the end.
Tips: Go early in the morning to avoid crowds and heat. There’s an entrance fee and parking charge. Bring water, it gets hot on the trail.
Located just above the outskirts of Waikīkī.
Mānoa Falls. Photo by Sarah Burchard.
Why go: A lush rainforest hike leading to a 150-foot waterfall, especially impressive in winter when rains are frequent.
Trail details: 1.6 miles roundtrip, relatively flat but can be muddy.
Tips: Wear shoes you don’t mind getting dirty. Swimming at the falls is not allowed for safety reasons, but the scenery alone makes it worth the trip.
Makapuʻu Point Lighthouse Trail
Why go: A paved, family-friendly path with sweeping ocean views and a historic red-roofed lighthouse. In winter, you might even spot humpback whales breaching offshore.
Trail details: 2 miles roundtrip, gradual incline, fully paved.
Tips: No shade, so sunscreen and a hat are musts. Bring binoculars if you’re hoping to see whales.
Located just past Sandy Beach on the east side of the island.
Koko Crater Railway Trail. Photo by Nature's Charm (Shutterstock).
Why go: A challenging stair-master workout on an abandoned railway track, with unbeatable views of Hanauma Bay and east Oʻahu.
Trail details: 1.6 miles roundtrip but feels much longer — more than 1,000 steep “steps.”
Tips: This is short but intense. Bring plenty of water, and avoid the midday sun. Good for travelers who want a cardio challenge without committing to a long hike.
Waimea Falls. Photo by Wirestock Creators (Shutterstock).
Why go: A cultural and natural experience rolled into one — paved paths through a botanical garden lead to a swimmable waterfall.
Trail details: About 1.5 miles roundtrip, well-maintained.
Tips: There’s an entrance fee, but it includes life vests for waterfall swimming. Great for families who want nature without rough terrain.
Located on the North Shore across from Waimea Bay in Waimea Valley.
ʻAiea Loop Trail. Photo by Wirestock Creators (Shutterstock).
Hike this 4.8 miles round trip trail amongst Norfolk Island pine trees and lemon eucalyptus along the Halawa Valley. Expect gradual climbs and steep switchbacks as you make your way 900 feet to the top. This hike takes about three hours to complete, but once you reach the top you’ll be greeted with views of the southern coastline from Pearl Harbor to Le‘ahi (Diamond Head Crater).
Why go: A challenging loop that combines waterfalls, ridgeline views and the unique experience of walking around a crater rim.
Trail details: About 5 miles, muddy and strenuous with rope climbs.
Tips: Start early, bring plenty of water and expect to get dirty. Not for beginners, but incredibly rewarding for those seeking adventure.
Located at the end of Waiomao Road in Honolulu.
Why go: Known for dramatic ridgelines, sweeping ocean views and a sense of remoteness that few other Oʻahu hikes provide.
Trail details: 4 miles, strenuous, exposed ridges with drop-offs.
Tips: Not for the faint of heart. Do not attempt in wet or windy conditions. A GPS app is helpful since the trail can be confusing in parts.
Located near Kahana Bay on the Windsard side.
Check the weather: Winter rains make trails lush but also muddy and slippery. Avoid ridge hikes if heavy rain is forecast.
Start early: Trails are cooler, less crowded and safer before midday sun.
Bring the basics: Water, sunscreen, sturdy shoes and insect repellent are essentials.
Respect the land: Stay on marked trails and avoid trespassing. Many trails run near private property.
Know your limits: If you’re new to hiking, stick with beginner or intermediate hikes. Oʻahu’s ridges are beautiful but unforgiving.
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