Pony Express Tours

Express riders take it slow in Upcountry Maui

By: Marty Wentzel

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Pony Express Tours offers horseback
riding with a view.
Pony Express Tours doesn’t cater to clients who want to gallop across the countryside, wind flowing through their hair. Instead, it’s designed for the much larger population of visitors who want a firsthand look at the exceptional geography of Upcountry Maui more specifically, Haleakala, the island’s 10,023-foot dormant volcano without exerting too much effort.

Whether your clients sign up for the firm’s mellow ride across ranchlands or opt for the more rugged ride into the crater, they’re rewarded with breathtaking panoramas across dramatic expanses while their steeds do all the work.

Run by Doug and Kathryn Smith, Pony Express Tours was launched in 1983, and the company leased 100 acres from Haleakala Ranch in the late ’80s as a base of operations. Today, clients check in at its headquarters at a cool, crisp 4,000-foot elevation.

Far from an experienced equestrian, I signed up for the morning Haleakala Ranch Paniolo Ride, perfect for people who want to spend the entire day Upcountry just not on a horse. During two hours in the saddle, clients get terrific views and great information, after which they have time for visits to other area attractions like Surfing Goat Dairy, Alii Kula Lavender and Tedeschi Vineyards.

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Rides take place on the grounds of
the historic Haleakala Ranch.
With names like Amigo, Ozzie, Pegasus, Gigi and Little Man, the horses stood calmly as we took turns climbing onto their backs. Our guide, a cheery spirit named Gayle, shared her goals with the group.

“Number one is safety,” said Gayle. “Next, I hope all of you will learn something about our unique Hawaiian culture and history. Finally, my wish is that everyone on the trip will appreciate the beauty of our amazing surroundings.”

A trail winding through an aromatic eucalyptus forest culminated in a clearing, where we got our first look at historic Haleakala Ranch, Maui’s largest working cattle ranch. At 30,000 acres, it stretches from the ocean up to the border of Haleakala National Park, and it comprises a large portion of the island’s high reaches. As our group marveled at the gigantic pasture, Gayle spun stories of the paniolo (Hawaiian cowboys) who first arrived in Hawaii in the 1830s and continue to work the land today.

Ambling along trails crisscrossing the ranch’s steady slopes, I was astounded by the vastness of the scene. Above us was the summit of Haleakala, 6,000 feet away, yet it felt close enough to touch. In the other direction, the entire central valley of Maui spread out below us in a patchwork of greens, while beaches sparkled to the north and south and the ocean seemed to stretch to infinity. Everyone took turns posing in front of the spectacular backdrop as Gayle took pictures of us with our cameras.

Cows grazed with abandon as if they owned the place, and mothers mooed their warnings while protecting their calves. Gayle pointed out trees and flowers of interest while skillfully guiding our group along the gentlest paths.

Nose-to-tail, the horses kept a steady pace back to headquarters. Juice and water awaited us as we wrapped up the ride, a relaxed and inspiring way to spend a morning in the beauty of Upcountry Maui.


Pony Express Tours

Tours across Haleakala Ranch include the two-hour morning Paniolo Ride for $105 per person and the 1½-hour afternoon Mauka Ride for $90 per person.

Pony Express also offers a four-hour Crater Ride into Haleakala Crater for $175 per person, with a picnic lunch.

Clients should wear long pants, closed-toe shoes, a sweatshirt and sunscreen. Raingear is provided. Participants must be at least 10 years old and weigh no more than 235 pounds.

Commission: 10 percent