Our 5 Favorite Holoholo Challenge Trails | Hawaiian Airlines

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Our 5 Favorite Holoholo Challenge Trails

With our inaugural Holoholo Challenge racing towards the finish line, our employees share their five favorite local trails to run or hike.


We couldn’t be more proud of the nearly 12,000 participants in our inaugural Hawaiian Airlines Holoholo Challenge. From Magic Island to Billings, Montana, to Boston, Massachusetts, runners across the country are sharing photos, inspiring stories and words of encouragement on our Facebook group page and with the #HoloholoChallenge hashtag. The virtual community you’ve created has inspired all of us to lace up our shoes and hit the trails – not because we have to, but because we can’t wait to.

For those still running and walking their “Mauka to Makai” or “Around Oahu” courses, we thought it would be fun to share some of our favorite island trails, chosen by our own Hawaiian Airlines employees. And for those of you who’ve already broken through the virtual finish line, it’s always a great day to get out of the house, breathe in the fresh, floral air, and get in a good run in the sun.

So double-knot those shoes and let’s go.

Photo courtesy of employee Malia H.

Aiea Loop Trail
5 miles

The Aiea Loop Trail is popular with local families and is great for trail runners. Located in central Oahu, it features views of the southern coastline, the H-3 freeway, Pearl Harbor and even Leahi (Diamond Head) in the distance. About two-thirds of the way through, be on the lookout for the remnants of a B-24 Liberty Bomber airplane that crashed here in 1944. To get to the trailhead, enter Keaiwa Heiau State Recreation Area, where you’ll find plenty of parking and restrooms.

"This is a great trail for the whole family. It’s a fairly easy trail, that’s about 5 miles. As you walk, you can smell the strawberry guava that are found all along the path. You also can get a great view of the H3!" – Malia H.

Photo courtesy of employee Kevin S.

Ala Moana Beach Park
2 miles, 3 miles w/Magic Island Route

Right across the street from Ala Moana Center, Ala Moana Beach Park is a true local’s beach. In the past, you’d find potluckers picnicking, swimmers in the calm waters, and walkers, runners and bike riders cruising along the paved paths every day. Today, while there are fewer gatherings, you can still find many out and exercising with social distancing in mind. It’s only a two-mile run around the park, but add a jog around Magic Island for a full three miles. The Magic Island peninsula treats you to beautiful views of Leahi (Diamond Head) on the east side and the cityscape of Kakaako and Downtown Honolulu on the west.

“Running in the Ala Moana and Kakaako area is great because you’re always near an amazing view of the ocean. Whether in the morning before work or in the evening after a long day, running along the ocean while listening to my favorite music makes the miles melt away.” – Kevin S.

Photo courtesy of employee Nicky T.

Kuliouou Ridge Trail
4.5 miles

While Makapuu gives you views of the makai, or ocean-side of East Oahu, Kuliouou takes you to the mauka side, or mountain-side, and is another great trail that locals love. With a 610-foot elevation gain, this is a challenging trail to run but an enjoyable day hike. You’ll trek through rocky terrain and dense pine forests to get to an amazing, scenic view overlooking the south side of Oahu.

“My family and I love hiking this trail (especially our pup!). There’s a ton of opportunities to stop for scenic views and photos along the way, so don’t forget your phone or camera. The trail is mostly shaded and has a nice incline if you’re looking for a workout. Kuliouou Ridge Trail is a popular hike and located in a residential area, so be mindful of the neighbors and come extra early to find parking (and beat the heat)!” – Nicky T.

Photo courtesy of employee of Karlie S.

Makapuu Lighthouse Trail
2 miles

This popular hike on the eastern tip of Oahu can also make for a challenging run. It’s a 500-foot elevation gain to the top, but you’ll be rewarded with incredible views of the deep-blue Pacific and the historic Makapuu Lighthouse, built in 1909 on a 600-foot sea cliff. Since the trail is paved, this an extremely popular hike, so go early to avoid the crowds and find a parking spot (note that the parking lot opens at 7 a.m., but you’re able to park along the road if you choose to arrive earlier). And bring plenty of water too – this side of the island offers some of the best, elevated ocean views on Oahu, but it can get hot.

“If you’re looking for a breathtaking view of Oahu’s southeastern coastline without a long hike, the Makapuu Point Lighthouse Trail is the hike for you! This trail is especially great for strollers and young children, as it’s paved the entire way up. You may even catch a glimpse of migrating humpback whales in season (November through May).” – Karlie S.

Diamond Head Loop
4.6 miles

While most visitors choose to hike to the top of iconic Leahi (or “Diamond Head,” as it is most commonly known), most locals prefer to run around it. This 4.6-mile run takes you from Kapiolani Park on the edge of Waikiki to the Diamond Head Lookout, where you can enjoy panoramic views of the south shore and spot local surfers catching the afternoon waves. There’s a 200-foot elevation gain during your run, so be prepared for a sweat. And don’t forget to bring quarters for the metered parking around Kapiolani Park.

"This is my go-to run at just over 4 miles. I recommend running at sunset as it’s cooler, and you get great views of the surf from Diamond Head Lookout. I prefer to start at the corner of Paki Ave and Monsarrat and run clockwise. This way, you get the hilliest part over with at the start and can enjoy beautiful ocean views as you run down from Diamond Head Lookout." – Hilary P.

Story By Brian Watanabe

October 22, 2020

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