From Pony Rides to the Maryland Million

By Mackenzie Pfeiffer

There’s a certain kind of Maryland horseman whose story feels stitched into the fabric of the state’s racing history – steady, genuine, and quietly devoted. John E. Williamson III is one of them. His new car has nearly 80,000 miles on it, and he describes the day as one that “smoked” his feet. Still, he rises at any hour to watch his beloved filly train before heading off to work – splitting his time between the racetrack and a funeral home – to support himself and his horses.

When you talk to Williamson, you get the sense that every story begins and ends with a horse. From leading pony rides to breeding Maryland-bred winners, his journey spans decades of change, capturing the enduring spirit of local racing – one built on patience, hard work, and an unshakeable love for the animals at its heart.

Mackenzie Pfeiffer (MP): You’re originally from the area yourself, right? A born and raised Marylander?

John E. Williamson III (JW): Right. I was raised in Pikesville and moved out to Joppa Road in the 1950s when my mother and father bought an old barn and turned it into a house.

MP: Were your parents involved in horses? How did you first get involved?

JW: No, my parents weren’t horse people. I got into horses through Windy Valley Farms, over by Falls and Joppa. They had an ice cream place back then [with] hamburgers and pony rides. They had a ring, and I’d go lead ponies around all day for work.

MP: That sounds like a classic local spot. How did you go from pony rides to thoroughbreds?

JW: A few of us would ride all through Green Spring Valley on the weekends - all the way to Sagamore, before the highway went in. We’d swim our ponies in the stream and everything.

The gentleman who owned Windy Valley had a few racehorses, so I got started with the usual things: rubbing horses, riding a little bit, and going to the races. I went everywhere – Bel Air, Cumberland, Hagerstown, Marlboro, and Timonium racetracks.

As I got older and outgrew my pony, I got a retired racehorse. One thing led to another. I started helping J.C. (Jerry) Meyer from Canada, and even spent my summers up there. I worked at Woodbine, Pimlico, Bowie, and Laurel. All over.

MP: Horses took a brief pause while you served in Vietnam. Did you know you’d return to them after?

JW: Not really. I was in Vietnam in 1967 and 1968. When I came home, I was living with my mother and staying out late. One night, I came home and she was sitting at the kitchen table waiting for me. She said, “I’m not putting up with this. This is my house. You’ve got to find something to do.”

I was 28 years old at the time, so I called J.C. Meyer. Back then, there was always a track running. He gave me a string of horses to train, and we each had our own side of the barn.

MP: How long were you training full-time?

JW: Oh, I still give my input on my horses at the track – so I never really gave it up!

MP: You’ve worn plenty of hats in the horse world, but you also work outside of it. How did your job at the funeral home come about?

JW: Racing was getting tough to make a living about 10 or 15 years ago, and I was getting tired. One day, I walked into a funeral home in Reisterstown and asked if they had any work. They said, “You’re hired. You can start tomorrow.” So, I went and bought a suit.

MP: Do you get to Laurel to see your horses train often? How does your trainer, John E. Salzman, Jr., take to your involvement?

JW: I was there all weekend and Monday. I left her (Stickwiththecolors) alone today (Tuesday) – but I’ll be there tomorrow if it isn’t raining.

John and I have butted heads a couple of times; maybe I’ll say something, and he’ll get ticked off. Then he’ll say, “Too many trainers in this barn.” It’s a good partnership. He’s helped me get five wins each with Stickwiththecolors and Mysisternancy. And he knows if I want a story, I’ll read a book.

I contribute a lot with my way of thinking. The way my horses are raised from birth, and getting a rest while they’re racing. They go outside, drink well water, have hay year-round, and Strategy feed. Nothing but Strategy.

MP: It sounds like they really get to be horses. Tell me about your mare Parade of Colors – quite the broodmare. How did you get her?

JW: That’s another story. Marshall Silverman was the agent for her as a yearling, and we partnered to buy her when she didn’t meet her reserve at the sale. We sold her as a two-year-old, and Tim Keefe trained her early on. I always kept an eye on her.

Jamie Ness claimed her later, and one day at the track, I told him, “If you ever get tired of her or you’re done with her, I’d like to have her.” He talked to the owners, and they gave her to me. I just wanted to give her a good home – I didn’t always plan to breed her, but anyway, that’s what happened.

MP: What drew you to her?

JW: Her eye. She just had a good eye on her. They’re like my kids; I don’t like to sell them. She hasn’t had a foal in three years, but she’s out on the farm covered in dapples.

MP: How about your filly, Stickwiththecolors, in the Maryland Million Distaff this weekend? She is one of several winners Parade of Colors has produced. How do you think the race sets up for her?

JW: She’s got speed – definitely. But she’s got the kiss of death with the one post. I just hope she’s not gassed on the front end. She’s been training great, she’s sound, not a pimple on her. She didn’t like the tight turns at Timonium last year, but she loves Laurel – ran huge all spring.

She runs best when she’s fresh; you can see it in her form. (Jevian) Toledo fits her perfectly. He’s worked her every time since I brought her back – around August 11th or 12th. I hope this is our race. She’ll be with the pace – I just hope she’s not the rabbit for the rest of them. I’ve already been looking at the stud book…dreaming.

MP: Fingers crossed she gets a breather along the way. Looking at her form, she is a true Maryland girl – she’s never run outside the state! Have you always bred to Maryland sires?

JW: Yep, she’s never left the state. I started breeding probably 30 years ago, when the man who owned Windy Valley Farms gave me a broodmare – Legs of Mystery. That was her name. Knowing everyone around here, I always liked to breed to local stallions. I even had some luck with breeding the first winners for a few of them.

When I bred Parade of Colors, I looked to Country Life and Merryland Farm. They had a new stallion, Cal Nation, who was pretty well bred. The first foal was a colt – he ended up being the first winner for Cal Nation.

That was Parade of Nations. I always like to combine the mare and stallion names for the foal; it suits this family well. Although I did name one after my sister, Nancy, that was Mysisternancy.

MP: That’s special – truly homegrown success. I heard a tip that your Maryland racing roots even show up in your home décor. What does your collection look like?

JW: Ha! There isn’t an empty space. I’ve collected things since I started on the racetrack – auction items, programs, posters, hunt scenes – from Woodbine to all over the Mid-Atlantic. It’s a mix.

MP: Is there one piece that stands out?

JW: I have this poster titled Saluting the Sport of Kings from 1974. The U.S. Postal Service had put out a stamp on horse racing. One day, I walked into the post office and asked the postman about it. He gave me the poster—and that started it all.

MP: Little did that postman know what he was starting. Of all the horses you’ve seen, do you have a favorite that isn’t one of your own?

JW: Buckpasser. I was stabled at Belmont Park when I first worked for J.C., and I used to go over to Buckpasser’s barn. They’d show him to me – he was just a nice horse at that time. It was a good outfit from the Phipps breeding program, the real old guard. Maybe we need more of those around today.

MP: A true classic. If you could give one piece of advice to someone who wants to get involved in racing or breeding, what would it be?

JW: Be patient. And have a bit of money – or be willing to work for it.