While hiking on O‘ahu’s windward side is limited, the few options available cover the range from a workout to a moderate hike to a simple stroll; you’ll find the scenery for each hike is fairly unique, too. Biking is equally limited, with cyclists confined mostly to roadways and a few trails, but since Kailua is a very bike-friendly town, that won’t be a problem for most.
For a great cardio workout and 360-degree views of the southeast shore, the Koko Crater Trail is a daunting 1,048 steps up the south side of Koko Crater. The stairs, actually railroad ties, follow the track of an old World War II military tramway that took supplies to the top of Koko Crater more than 1,000 feet to the summit. At the top you’ll find several cement military installations and amazing views all around. From Kalanianaole Highway, turn mauka onto Koko Head Park Road and park in the Koko Head District Park parking lot. It’s about a 0.25-mile walk to the base of the stairs.
There is a popular walking trail along Kawainui Marsh, one of the few wetland ecosystems on O‘ahu and home to several species of native waterbirds like the Hawaiian coot, Hawaiian moorhen, and the Hawaiian stilt along with a host of other feathered inhabitants. The mile-long path is a raised, paved trail that crosses the marsh from Kailua Road to Kaha Street, off Oneawa Street on the north end of the Kailua neighborhood known as Coconut Grove.
Maunawili Falls is a short hike in the shadow of Olomana that follows Maunawili Stream and terminates at the falls. From Kalanianaole Highway, turn into A‘uola Road in the Maunawili neighborhood. Immediately fork left onto Maunawili Road and follow it through the subdivision and a forested area to the end at Kelewina Street. Park near the intersection and continue on foot on the one-lane private road. A sign indicates the way to the falls, which in part is on private land, so stay on the trail. Along the stream look for ‘ape, a plant with huge, elephant-ear-shaped leaves. A ridgeline section offers views of Ko‘olau Range, Olomana and Kane‘ohe Bay. Regain the stream and follow it to a large, deep pool and Maunawili Falls. On the hike you’ll cross the stream several times and the trail can be quite muddy. It is also very popular and heavily used on the weekends. There is a second smaller pool at the top of the falls and the trail continues back from there if you wish to continue exploring the forest.
Kailua is the most bike-friendly town on O‘ahu. The beaches and neighborhoods are in relatively close proximity to the town center, where all the dining, shopping, and services are located. The town is flat, the weather is exceptional, and the traffic is usually so congested that it’s faster to get around on two wheels. In addition to riding around town, bikes are allowed on the trail that crosses the Kawainui Marsh.
Because of these factors, Kailua is home to the first bike share program in the state. There are two Hawaii B-cycle kiosks in the town center: 767 Hamakua Drive (near the intersection of Hamakua Dr. and Kailua Rd.), and 515 Kailua Road (near the intersection of Hahani St. and Kailua Rd.). Simply swipe your credit card at the kiosk, grab a bike, and go. When you park the bike at either location, your card is charged for the time you used it. The cruisers come equipped with a lock, comfy seat, and baskets.
Or you can rent a bike the traditional way, from an outfitter. The Bike Shop (270 Kuulei Rd., 808/261-1553, 10am-7pm Mon.-Fri., 9am-5pm Sat., 10am-5pm Sun.) is a full-service bicycle shop. They rent 21-speed cruisers for $20 per day and road bikes for $40 per day. Kailua Sailboards & Kayaks (130 Kailua Rd., Ste. 101B, 808/262-2555 or 888/457-5737, 8:30am-5pm daily) rents bikes for $25 a full day and $85 for seven days.