Lopers Award for Favorite Person of 2010

Jesse Taylor Lana'i

Every day this week I will be highlighting a favorite travel experience from 2010 with something I call the Lopers Awards. Today I want to share with you my favorite person I met while traveling.

It will come as no great shock to anyone that I loved vacationing on the Hawaiian island of Lana’i. What may surprise some is that my pick for the 2010 Most Interesting Person I met while traveling was on this remote island.

We had finished a gorgeous three hour horseback ride through the Lana’i highlands and were back in the Koele stables, cleaning up and guzzling bottles of water. While we were decompressing, a young guy with a slight build and gigantic cowboy hat approached with guitar in hand and asked if we’d like to hear a song. This was Jesse Taylor, one of the two wranglers at Koele and as I would soon learn, a real life singing cowboy.

We all sat on the porch of the stable house and listened as Jesse serenaded the group with a song befitting of any major recording artist, except he had written it himself. I spoke with Jesse afterwards and quickly learned that there was much more to this modern day cowboy than first meets the eye.

Jesse is 23 years old and hails from Arlington, Washington, a small logging/dairy farm town in the western part of the state. His mother was named after a Johnny Cash song and his dad is a songwriter and team roper, so Jesse’s emergence as a singing cowboy may have been a foregone conclusion.

A couple of years ago, he was traveling around the country, playing music and living out of his truck when he had a chance encounter in Montana. He was playing music in a tiny town when a stable manager noticed him and asked Jesse is he wanted to ride horses and play music in Hawaii. He thought it was a joke at first, but two weeks later he found himself on a plane heading towards Hawaii.

Koele Stables

If you ask Jesse if he considers himself to be a cowboy, he would quickly say that he is a rodeo cowboy and not a true paniolo. The western spirit is alive and well in many parts of the country, and Hawaii is no exception. There is a proud history of ranching and riding in Hawaii and while Jesse is a new-comer to the islands, he is immensely proud of their tradition and his role in helping to keep it alive going into the 21st century.

Lana’i draws a lot of people for a variety of reasons. Some want to get away from the world, others want to discover more about it. Jesse definitely isn’t running away from anything and for him Lana’i has been a great experience, but probably not a long term one. His heart is with his music and because of that he will undoubtedly find himself in Nashville, forming a band and selling his music.

He’s not a get-rich-quick kind of guy though, he deeply believes in the power of music and what that power can do for others. Jesse is a true musician that simply loves to play and hopes that his music will give comfort to people as they experience their own tough times.

I wasn’t expecting to meet someone like Jesse Taylor on Lana’i, but I’m glad I did. He showed me a different side of the island I didn’t realize existed and helped me understand that the reasons why tourists love to visit are the same that motivate people to call it their home.

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By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer. Also follow Matt on Twitter, Facebook and

8 Responses

  1. Andi

    I love the idea of giving out awards!!! This guys sounds like such a lovely person. 🙂

    Reply
  2. ayngelina

    Wow you know I would have never suspected there would be cowboys there.

    Reply
  3. Lori Patrick

    Aloha Matt – What a timely post. Found it by googloing Jesse Taylor Koele…
    Was checking for a Jesse Taylor Website…

    We have been on Lanai for the past few days and I had a trail ride with Jesse. We laughed alot and told stories. What a genuine guy. And his voice !!!! I agree – songs and voice befitting of any major recording artist. I asked him if he had ever considered American Idol and he laughed. “Nope, I believe in the old fashioned way – one person at a time. I figure if I keep playing for people the right person will come along” Good Luck Jesse !!

    Reply
    • Matt Long

      Wow really? So glad you found us and that you liked the post. Jesse is a neat guy and I hope he gets that big break one day!

      Reply
  4. Jesica Shattuck

    This is so cool! I know who Jesse is because of my cousin. Her boyfriend is really good friends with him. He has been camping with us a few times and is such a good singer!

    He’s pretty funny tooooo.

    Reply
  5. Christie Pater

    I have known Jesse my whole life, We grew up together as kids and as far back as i can remember he has always wanted to be a country singer and write his own songs. I am so proud of him for going to all the places that he has and writing as many songs as he has. I know you make an impression on people Jess. I love the fact that people are getting to listen to you music and you are traveling. Better than being stuck here in Arlington with the rest of us! I wish you the best of luck and i am so glad to have you as my one of my best friends! You will do great in what ever you do, I cant wait to see you when you come home. Love ya!!

    ~Chrisite

    Reply
    • Justin Donnelson

      Christie Pater, I agree that Jesse is going to be big someday! I know Jesse and saw this many years ago. It’s fun to find him now still following his passion even in Hawaii! That article so describes the Jesse I know.

      Reply
  6. Justin Donnelson

    This is the Jesse Taylor I know from Arlington, WA. It’s fun to find him still chasing his passion! I remember when I worked with him many years ago. He was writing music and playing the guitar every chance he could! What a great article and to the T on what Jesse Taylor is like! Thank you, Justin Donnelson from Arlington, WA.

    Reply

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