There are a lot of adorable kids and ponies at Lendon Gray’s annual Youth Dressage Festival, but when we spotted a photo of 10-year-old Owen Sheldon on his pony Macho Man trotting down centerline, seemingly dwarfed by the arena letters, we knew we had to get the story on the pint-sized pair.

This was Sheldon’s fourth year with Gray’s Dressage4Kids program. At the festival, held July 13-15 in Saugerties, New York, he finished 10th in the walk/trot/canter, 12 and under, A division, with an overall score of 73.83 percent. (Riders complete a written test, then perform a dressage test and an equitation test.)

Two determined faces. Photo by Amy Dragoo Photography.

“It was really good for us,” said Sheldon. “We got some really good scores. I’m super proud of him. I’m really happy with what me and Macho have accomplished.”

Sheldon’s mom Angie Sheldon explained that the whole family got involved with horses through her daughter Lucy Sheldon, who asked for lessons four years ago when she was 9.

The family lives in Brooklyn, New York, but has a house in Ancram, New York, and Lucy and Owen, who was initially just along for the ride, started taking lessons from sisters Lisa Herman and Amy von Scholz at Blue Ribbon Farm and Academy. Angie soon followed her children’s interests and started riding two years ago at age 51, and she now has two horses of her own.

Both trainers had been involved with the Youth Dressage Festival and encouraged Owen and Lucy to compete. Owen’s been free leasing 17-year-old Macho Man for three years from his owner Chelsea Miritello after she outgrew him.

This year he was planning on taking a rescue pony, Jersey Girl, to the festival, but she died unexpectedly in April.

Owen Sheldon and Macho Man competing at the Youth Dressage Fesitval. Photo by Amy Dragoo Photography.

“Heartbroken doesn’t even begin to describe it,” said Angie. “She was my daughter’s pony, and Owen had been riding her because Jersey could jump more than Macho Man. He was trying to do some more hunter/jumper things with her.”

Since Owen had competed Macho Man at the festival before, it seemed like a natural choice to bring him again. Angie thinks Owen will outgrow the 10-hand Shetland cross by next year, so this year is their last hurrah.

Macho Man is not an easy ride, but Owen has stuck with it and loves his pony.

“From the very beginning it was a match made in heaven, however Macho Man is a very opinionated pony,” said Angie. “He has a huge personality. A lot of the children are afraid of him. His canter is a bit fast and bumpy, so it’s hard to stay seated in the saddle. He makes it very difficult to steer him, and he’ll drop his shoulder on you. Owen broke his collarbone two years ago because he dumped him.

“Owen loves this pony so much; he wants Macho Man at his wedding, which hopefully won’t be for a number of years!” added Angie with a laugh. “I don’t know if Macho Man will be around. But he has this vision of Macho Man being his best man at the wedding. I kind of knew that he was going to be in our lives for a while, so I had bought an Amish cart. Lisa knows how to drive a cart. When Owen broke his collarbone she taught him how to drive.”

Owen Sheldon with trainer Lisa Herman. Photo courtesy of Angie Sheldon.

A little shaken up, Owen took his time getting his confidence back once he healed.

“Owen is incredibly brave when it comes to these things, and it didn’t take him that long to get back up and running,” said Angie.

Macho Man likes to bite, so you have to be careful around him. “I have been bitten personally by Macho Man on many occasions,” said Angie with a laugh. “When you go to pick his feet he flips his head around and bites you in the butt.”

Owen says that Macho Man lives up to his name at the barn too.

“He’s very fierce,” he said. “He goes in a paddock with four other horses, and he’s the leader of all of them. He’s a very enthusiastic eater. For example on our one-year anniversary my mom got him cupcakes, and he got frosting all over him.”

Macho Man is also a talker. “His whinny is very distinctive,” said Owen. “It’s very loud, and he’s very social, especially during our rides.”

Angie said Owen is often the only boy at horse shows, but he has a passion for dressage even though he’s started jumping more recently.

Owen with his 10th-placed ribbon. Photo courtesy of Angie Sheldon.

“I think the best thing he could say is that he likes bonding with Macho Man and learning how to get him to do all the maneuvers and learn a test and successfully complete a test,” Angie said. “The dream is to someday get a freestyle going to The Village People’s ‘Macho Man.’ ”

Owen got his highest scores ever at the festival, including a 9.5 on his final halt on Saturday.

“It was pretty amazing because the pony does not like to halt where he’s supposed to, but Owen went straight down centerline and did it perfectly,” said Angie. “Plus he went into his corners and had better geometry than he’s ever had and some of the best free walks he’s ever had. It was a really nice show for him.”

Owen said that it was “kind of” scary to warm up among bigger horses at the show and that while Macho Man can be difficult, “after a while it gets pretty easy. You just have to stick with it.”

Whatever Owen does next, Macho Man will be a part of his life. “He’s very firmly a part of our family,” Angie said.

Do you know of a kid who loves dressage or rides an unusual breed? Let us know by emailing Lindsay at lberreth@coth.com.