About Us

All About Pony Express Tours

Pony Express Tours has been running rides on Maui since 1983, a family run operation with Doug and Kathryn Smith on the lead horses and followed up by kids Nicole and Allison.

The origins of the Crater rides go back to 1980, when Doug was hiking through the crater on foot one day and had an epiphany about what a great idea it would be to see it by horseback! The horse does the walking and you are truly free to sit back and look at the views. At that time there was not a horseback operation, so after checking with the National Park he started trail rides into the crater.

It took a number of years to bring the operation together with humble beginnings: borrowed trucks, trailers, and leased horses with good friends. Now 30 years later we are proud to report that the popular guidebook, Maui Revealed, rates the crater ride the number one horseback ride in the state!

The shorter Ranch Rides began in the late 80’s when we leased over 100 acres from Haleakala Ranch as a base of our operation and started running rides across the Ranch.

Those rides appeal to people looking for a shorter ride and views of the island and ocean. Most people make an “upcountry day” out of it – do a horseback ride, see the crater, have lunch, view Makawao or Tedeschi Winery…