Help keep our trails and parks open during COVID-19 by committing to social distancing. Some trails or park services may be closed this weekend so check with local authorities before heading out.
Learn more

Best trails in Kailua

6,330 Reviews
Looking for a great trail near Kailua, Oahu? AllTrails has 12 great hiking trails, trail running trails, views trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Ahupua'a O Kahana State Park or He'eia State Park, we've got you covered. You'll also find some great local park options, like Keaiwa Heiau State Recreation Area or Kailua Beach Park. Ready for some activity? There are 7 moderate trails in Kailua ranging from 1.6 to 6.3 miles and from 49 to 1,515 feet above sea level. Start checking them out and you'll be out on the trail in no time!
Show more
Map of trails in Kailua
Top trails (12)
#1 - Kaiwa Ridge (Lanikai Pillbox) Trail
Kailua Beach Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1865)
Length: 1.8 mi • Est. 1 h 10 m
Great short rocky steep hike along the Ka'iwa Ridge offers great views of Lanikai and Kailua. Near Waimanalo Beach - wonderful white sand and calm water, Lanikai and Kailua Beaches The Kaiwa Ridge Hike is great to go either sunrise or late afternoon short 0.6 mile each way but gains 500 ft so is steep in places with great views along the way - It takes about 30 minutes or less to hike from the trailhead to the top (second) pillbox (elev. 565-ft). Its another 10 minutes to reach the ridge's highest point (elev. 603-ft) marked by a geodetic marker (the small concrete platform with broken surveyor's pole). The "official" trailhead, unmarked, is about 40 feet uphill on a paved, private driveway along Kaelepulu Drive. The driveway is opposite of the Mid Pacific Country Club & Golf Course just before you reach an exclusive, gated community. The first part of the trail is very steep, slippery, and can be confusing. This trail is undeveloped. The trail is rocky, windy and rewards you with a great view on top of the pillboxes. No guardrails so can be dangerous for young children. Also the trail is very poplular and can be crowded.Show more
#2 - Maunawili Falls Trail
Waimanalo Forest Reserve
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(1898)
Length: 2.8 mi • Est. 1 h 39 m
This trail begins in a residential area. Please be mindful of residents, be quiet, and park legally. There are no bathrooms or other facilities at the trailhead. Please use the restroom before you come and pack out all trash. The rainforest in this area sees a lot of visitors, so it is important to minimize your impact in every way you can. A nice hike through the jungle to great view of Kailua, Maunawilli Falls, and a swimming hole. Maunawili Trail contours the base of the Koolau Mountain Range on the windward side. It begins off the Pali Highway and ends in Waimanalo. It offers spectacular views of the windward side of Oahu, Olomana, and the Koolaupoko watershed. Vegetation along the trail includes mountain apple, rose apple, ti, naupaka, mamake, lobelia, koa and ohia. Maunawili Trail is a good family trail. There are three access points for this trail. The Maunawilli Falls Trail is a great hike in Kailua along the river that eventually stops at a beautiful waterfall with a great swimming hole below. Many people like to jump from the waterfall into the pool below, and some with a bit more courage even climb higher to the side of the waterfall to jump further (try at your own risk). The trail is often muddy, especially after rains, and you will cross the river several times along the trail. About half way through the hike you will break out of the trees for some nice views of the surrounding mountains and views towards Kailua in the distance.Show more
#3 - Olomana Trail
Mount Olomana State Monument
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow Star(1377)
Length: 4.4 mi • Est. 2 h 57 m
Please note: There is no parking area at the trailhead - the map shown here will direct you to street parking and you can walk to the trailhead from there. Users have reported that there are towing operations in the area. It is not clear where the legal parking is, so park at your own risk. Located in Kailua, on the windward side of Oahu, Olomana Trail (three peaks) is a strenuous hike with amazing views if you can make it to the top. The trail can be accessed from the intersection of Maunawili Road and Auloa Road off of Pali Highway. The first peak, Mount Olomana, is about 1.5 miles up with steep drop-offs on both sides and takes about an hour and a half to get to. Toward the top there are some rock climbing elements. The top of the first peak offers 360 degree views. It is steep on the downhill slope towards the second peak. The next peak isn't as challenging but still has an excellent view. The last peak should only be tried by experienced hikers in good shape and requires ropes all the way up. To return to your car you must go back the same way you can. This a favorite hike in Oahu, however can be very challenging with all of the up/down.Show more
#4 - Likeke Falls Trail
Nu'uanu Pali State Wayside
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(640)
Length: 0.8 mi • Est. 28 m
#5 - Kayak to Moku Nui from Kailua Beach Park
Kailua Beach Park
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow Star(64)
Length: 4.8 mi
Note: As of August 2020, the island is closed for visitors however you can paddle near/around it. This is a kayaking/canoeing route, not a hiking trail. On Sundays, visitors are not allowed to go to the islands or rent kayaks/canoes. However, on Sundays visitors can rent paddle boards. Pick up kayaks from Kailua Beach Adventures and just walk them to Kailua Beach to start.Show more
#6 - Ohana Trail
Waimanalo Forest Reserve
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(104)
Length: 3.2 mi • Est. 1 h 16 m
Note: As of September 16, 2020, users have reported that the Maunawili Golf Course entrance is CLOSED due to Covid-19, so you will have to enter from the Waimanalo side. Ohana trail was built in 2013 by a dedicated group of mountain bikers seeking permanent access to an area used for many years for recreation. Representing themselves as OMTBO - Oahu Mountain Bike Ohana, they sought and were granted permission from the state land agencies. Through continued dedication and many hours of hard work, volunteers continue to maintain the trail. As it was built by and for mountain bikes, please expect that you will see many of them and give right-of-way accordingly. Mahalo!Show more
#7 - Kawainui Marsh Trail
Kawai Nui Marsh
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(113)
Length: 2.9 mi • Est. 1 h 17 m
A beautiful and relaxing walk. The park is open 7 AM to 7 PM. The trail surface is paved or gravel and typically at least four feet wide. There are sections where grass is growing up through the trail that may make the surface too difficult for wheelchair and stroller users to traverse without assistance. The grade is also moderately steep - with multiple sections between 8% and 12% estimated grade. Show more
#8 - Kailua Bay Beach Walk
Kailua Beach Park
easyYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(59)
Length: 5.1 mi • Est. 2 h 10 m
#9 - Maunawili Falls via Pali Highway
Nu'uanu Pali State Wayside
moderateYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray Star(28)
Length: 6.3 mi • Est. 3 h 32 m
#10 - Maunawili Trail from Waimanalo
Waimanalo Forest Reserve
hardYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarYellow StarGray StarGray Star(42)
Length: 8.8 mi • Est. 6 h 13 m
Showing results 1 - 10 of 12