Horsing Around on O‘ahu’s North Shore with Happy Trails Hawai‘i

Don’t let the tourists have all the fun. Excellent views of the North Shore, a killer ab workout and learning from a polo player-slash-referee are only a few of the reasons we shouldn’t miss out on such an awesome outdoor activity.


Horse riding

Gif: Katie Kenny


ACTIVITY: Horse riding

COMPANY NAME: Happy Trails Hawai‘i

FOR THE ADVENTURER who loves animals, beautiful vistas and learning random facts and history about Pūpūkea and Waimea. Also, it is a great way to squeeze in a solid core workout outside of gym monotony.

LENGTH: Choice of a one-and-a-half hour or two-hour ride.

FEE: $99—$119 

WHERE: Pūpūkea, North Shore


SEE ALSO: 24 O‘ahu Hikes We Really Like


Off we go

It’s been a long time since I’d ridden but after the lesson and five minutes on the Scenic trail, I could relax and just enjoy the surroundings. Photo: Becca Gomez



Safety first! Each ride starts with a briefing and lesson so that everyone is more comfortable while riding their selected (by the instructors) horse. The animals we saw were sweet and obeyed all of the commands given, as long as the orders were delivered correctly and with confidence.


Lesson time with my guide, Becca.


Yes, the horses have very noticeable personalities. Our guide joked about how shocked some of her guests are when they begin to notice the personal quirks of each horse. Within the herd of 23 horses are seven polo ponies (who are ridden by instructors as guide horses), two retirees, who wander around sometimes bullying the young’uns, and 14 for trail riding. Some of these rascals are not concerned with taking you up to the best viewpoint of Waimea Valley—they are after the tastiest stretch of grass along the trail. This is when your lessons on how to control your horse are useful. When not out on a tour, the horses roam freely within the expansive grounds of the privately-owned ranch.


Tip from guide: “Walk in a single file line because these are polo ponies. They are a little competitive, so pass each other and you might start the Kentucky Derby.”


My lady knew to stay hydrated before her two-hour walk. Photo: Katie Kenny



Learning and listening. It doesn’t take too long to realize the owner and his crew of friendly guides are passionate about the animals, land and history of the area. Throughout the journey, our guide shared little tidbits about the environment, seasonal fruit along the trail (which you can sample), historical sites along the path and stories about events that took place there. This was one of the best parts of the experience: You can quietly take in views and fascinating stories, all while connecting with a beautiful (and constantly hungry) animal.


Photo: Katie Kenny


Photo: Katie Kenny


Photo: Katie Kenny


North Shore views

Gif: Katie Kenny



Whether you live in the city, close to the beach or in a quieter suburb, horse riding in the open fields and jungle forests of Waimea Valley is an easy way to escape for a couple hours. It felt like a mini trip off-island.


Horse Riding uphill

Yes, there are the big photo-op moments when you’re overlooking Waimea Bay but I much preferred trudging along the uphill paths in the thick of it. Photo: Katie Kenny


Oh, and did we mention how many calories you burn riding for two hours? Go on, you earned those tasty shrimp tacos from the food trucks down the road at Shark’s Cove (see, North Shore Tacos).


SEE ALSO: Open for Fitness: CorePower Yoga





  • Wear long pants. It’s best to go with comfortable denim but my active leggings (with breathable mesh strips) did me just fine on the hot and sunny day I went riding.
  • Wear items you don’t mind getting muddy. Leave the fresh white Adidas at home and grab a pair of your best hiking shoes (or boots if you have them). Remember footwear must be closed-toe!
  • Don’t be afraid to ask if you’re doing it right. The guides are very good at instructing all levels of riders but if you’re worried about your technique halfway through the trail, have them check you out. I found this helpful for two reasons: I felt more in control of my horse buddy and our ride together, and I didn’t want a sore back and hips from sitting incorrectly on the saddle.
  • Top it off with a hat. When you’re out in the open field you’ll want to focus on the views, not your overheating forehead.



All riders must be at least 6 years old, under 235 pounds and able to ride their own horse. Reservations are required and the company recommends booking two to three weeks prior to the day you want to ride.



Drive on Kamehameha Highway, past Waimea Bay, and take the right after Three Tables (just before the Foodland) onto Pūpūkea Road. Look out for the Happy Trails sign hanging on an open gate about one mile up the road.


Horse Riding Sign

Photo: Katie Kenny




Open daily, rides available 8 a.m.-5 p.m., 59-231 Pūpūkea Road, Hale‘iwa, (808) 638-RIDE (7433), happytrailshawaii.com