5 Best Oahu Running Trails with Views

04/30/2018 | by Courtney Dennis | Local Area Local Tips Oahu Things To Do Vacation Planning Vacation Rentals

What better way to experience the ultimate runner’s high then to explore the trails of Oahu?

Vacationing in Paradise doesn’t mean leaving your running shoes behind. Whether your goal is a comfortable jog or a challenging run, Oahu offers something for all fitness levels. With trails highlighting the natural and breathtaking beauty of the Island, you can experience the ultimate vacation while getting your miles in.

So, what are you waiting for? Grab your running shoes, water, sunscreen, and embrace the tropical beauty of Oahu!



#1 – Diamond Head Loop

Rewarded by the view of Waikiki and Honolulu in the background.

Overview: Ideal for an early morning or late afternoon run, Diamond Head is a great way to take in a view of Waikiki. Part of the Honolulu Marathon Course, it is a favorite local running route. Your run will take you past many local attractions to include Honolulu Zoo, Waikiki Aquarium, Kaimana Beach, and Kapiolani Park.


  • Approximately 4 miles of paved running trail
  • Loop – mixed flat surfaces and hills
  • Peak elevation 198 feet
  • Ocean views – start your day with a beautiful sunrise or end it with a gorgeous sunset
  • Bryan Clay Exercise Park offers open-air fitness equipment for public use
  • Kapiolani Park provides both water fountains and restrooms
  • Park for free at Diamond Head lookout, Kapiolani Community College (KCC) parking lot, or Paki Park on Paki Ave

Difficulty: Moderate

Stay: Vacation rentals in nearby Diamond Head, Aina Haina, and Niu Valley.


“Running the Diamond Head Loop is an adventure everyone should experience. Refreshing with exquisite views and incredible foliage, don’t let this opportunity pass you by!” – Karen (48) Seattle


#2 – Makapuu Point Lighthouse

The lighthouse is not open, but offers plenty of photo opportunities.

Overview: Makapuu Point Lighthouse is located on the hotter and dryer side of the Island making it the ideal choice for an early morning run. Stunning views of the ocean include the possibility of humpback whale sightings. Although the 1909 Lighthouse is not open to the public, several locations along the route provide photo opportunities. Heading back towards Oahu, you can stop at Makapuu Beach Park to enjoy a picnic with tables and bathrooms located at the park. Want to cool off instead? Sandy Beach is ideal for bodyboarding. Another option is snorkeling at Halona Blowhole or Hanauma Bay. Missed out on your early morning cup of java? Head to the Koko Marina and make a stop at the Kona Brewing Company.


  • Approximately 2 miles of paved running trail
  • Uphill trail peaking at 500 feet with stunning views of the windward coast and offshore islets
  • Open daily from 7:00 A.M. – 6:30 P.M. with parking at the site

Difficulty: Moderate

Stay: Vacation rentals in nearby Waimanalo, Lanikai, Kailua, and Kaneohe.


“Traveling to Hawaii to get away from work and recharge the mind and body peaked when I experienced Makapuu Point Lighthouse Trail. From the crystal clear views and the perfect weather, few things compare….stunningly Beautiful!” – John (55) Boston


#3 – Tantalus and Round Top Drive Loop

A tough 1,000 foot elevation gain, but at least there is shade!

Overview: One of the more challenging runs, this trail has an elevation increase of over 1,000 feet. Guaranteed a strenuous workout, you will be especially appreciative of the shade provided by the bamboo forests and eucalyptus groves. Along the route, switchbacks offer panoramic views of Honolulu and Waikiki.


  • Approximately 10 miles of paved surface
  • Run uphill for 5 miles then downhill for 5 miles for an invigorating and breathtaking run
  • Increases over 1,000 feet in elevation topping out at 2,014 feet
  • Entirely paved and almost altogether shady
  • The Nature Center has water and restrooms available
  • Park at the Hawaii Nature Center or Makiki Pumping Station on Makiki Heights Drive

Difficulty: Moderately Hard

Stay: Vacation rentals in nearby Kakaako and Kahala.


#4 – Waikiki Loop

Take in the sites and sounds of Honolulu with views of Waikiki Beach.

Overview: For an urban and yet still beautiful run, Waikiki Loop is a perfect choice. While taking in the sights and sounds of Honolulu, you will have fantastic views of Waikiki Beach and Diamond Head Crater.


  • Approximately 2 miles of paved surface
  • Outdoor exercise equipment to enhance your run is available nearby at Fort DeRussy Park.

Difficulty: Moderate

Stay: Vacation rentals in nearby Waikiki.


“I have been traveling to Hawaii for five years. Hawaii trail running is unmatched. The climate is perfect. The lush, vibrant vegetation is a masterpiece. Hearing the ocean is calming and soothing to the soul. It is an amazing experience.” – Andrea, 35, Tucson AZ


#5 – Kaena Point Trail

Views of the ocean, sea cliffs, tidal pools, and dunes.

Overview: Mixing things up, the Kaena Point Trail is a dirt road that was once a railroad bed. With a slight elevation increase of fewer than 200 feet, this is one of the easier runs on the list. However, don’t leave this Oahu trail off your list! You will feel as if you are part of something magical when you look around to see the incredible views of the ocean, sea cliffs, tidal pools, and dunes. And don’t forget the whales! During the winter months, it is likely you will spot one or more as you cast your eyes over the ocean and take in the beauty of your surroundings.


  • Dirt road spanning 4.5 miles
  • Elevation increase of fewer than 200 feet
  • For a two-mile run to Kaena Point, runners can start at Keawaula Beach and run to the point. For a two-and-a-half-mile run, runners can begin at the end of Route 930 and run to the point.

Difficulty: Easy

Stay: Vacation rentals in nearby Makaha and Koolina.



Challenge – Koko Head hiking trail, Oahu Island, Hawaii

If you are still up for a challenge, Koko Head hiking trail might be just what you are looking for! This run is one for the most dedicated of runners who genuinely want to push their endurance levels to the limit.

Are you ready for the burn? The views from the top are well worth it.

Overview: For running enthusiasts who want to take it to the next level, turning this traditional hiking trail into an uphill run offers the ultimate workout. A staircase created out of the 1,050 railroad ties abandoned by the rail line provides the ultimate fitness challenge. With an elevation gain of 990 feet, this is a strenuous run.


  • 1.8 miles out and back with an elevation gain of 990 feet
  • Parking is available in the lot at Koko Head District Park in Hawaii Kai
  • No shade – ensure you have water and sunscreen

Difficulty: Hard

Stay: Vacation rentals in nearby Hawaii Kai.



3 Ways to Expand your Running Experience

You have checked out the trails, are savoring your time in Oahu, but are still looking to add something to your vacation? Extend your running experience beyond a solo run on the world’s best trails.


#1 – From Marathons, Triathlons, to Iron Man Competitions, Oahu Has It All!

Want to bring it up a notch? Why not join a competition while on vacation? Hawaii is the ideal location for marathons and triathlons. Running in the USA offers the most extensive online directory of races and clubs with a complete listing of all events in Hawaii. Plan your trip around a competition combining your love for competing with a beautiful Island experience.


#2 – Guided Running Is Not Just for Beginners! Let the Experts Show the Way!

Don’t want to compete? Another option is booking a guided running tour. An increasingly popular way for runners to experience a new location, local experts offer a wide variety of running options. You can choose to personalize your run from any destination, selecting the distance you want to run and the difficulty level you want to take on.


#3 – Forgot Your Running Shoes? Not a Problem! Top Running Stores in Oahu Offer Gear and Networking For Runners  

Whether getting ready for a casual jog or a scheduled competition, these stores have all your fitness needs covered. Add that to the opportunity to get the inside scoop on running in Paradise from the locals who live here and share your passion!  

  1. Runner’s Hi: Founded by Raymond Woo, it is in the heart of Oahu. He is a seasoned marathon runner competing in well over 40 marathons and triathlons in his 30 plus year love affair with running
  2. Runners Route: This is the largest running specialty store in Hawaii. While priding themselves on having a wide selection of products and a knowledgeable staff, their goal is to ensure customers receive high-quality service to ensure they have a successful running experience.
  3. Running Room: “A Store For Runner….By Runners” pretty much says it all! Created as a place where runners could come together and socialize, Running Room is a family owned business priding itself on providing customers with the best in style, functionality, and fabric innovations at a reasonable price.


Incorporate your love for running and the top trails in the world and come to Oahu. We’re here to help you book a vacation rental that will be perfect for your Oahu running vacation.


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