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One-hundred sixty-five pounds. Not a goal. An ultimatum.

And not easy for a guy who’s 6-foot-3.

“I have to think a lot more about my weight now than when I was younger,” said two-time Maryland Hunt Cup winning rider Chris Gracie. “It’s all about staying busy and getting in the right habits.”

Gracie leans against the tailgate of his truck, zips up his down jacket and stretches a wool cap down over his ears. It’s a 60-degree late winter afternoon. We pick up a slow jog and start off down the driveway of the Middleburg Hunt kennels. Left on Foxcroft Road at the mailboxes.

Running to make weight is different from running for sport or recreation. Bundle up, jog slowly, and, above all, sweat.

“Muscle adds weight,” Gracie says, “So I have to jog slowly and walk up hills.”

The Kennett Square, Pa., native got his start in the horse business working in the stable at Mr. Stewart’s Cheshire Foxhounds kennels. He rode his first race under rules in 2003 while still in high school. The same year he picked up his first Maryland Hunt Cup win aboard Swayo for trainer Ann Stewart and owner Move Up Stables.

The toughest steeplechase on this side of the Atlantic and open only to amateur riders, the Hunt Cup eludes some jockeys for decades. Or even for their entire career. But Gracie walked into the winner’s circle after his first trip over the 22 post and rails and four boards – some towering to 4-foot-9.

“I’ve just been lucky to ride good horses and have good people around me,” he says, “I was in the right place at the right time.”

We settle into our pace, single file, as Foxcroft Road narrows and snakes between stone walls. The usually dry creek bed on the left babbles with last night’s rain. Mr. Goltra’s Red Anguses ruminate and reflect on the hill to the right. Across the pock-marked bridge that spans Goose Creek, the potholes acting like a tire drill at high school track practice. Another left on Snake Hill Road.

The trick, Gracie says, is to change things up. If you get bored, you lose. Or rather, stop losing. He does hot yoga or goes to spinning classes most weeknights and suits up for a run at lunchtime most days. It’s a balancing act that Gracie has had to manage carefully since returning to the sport after a 12-year hiatus.

Gracie’s second Maryland Hunt Cup win came in 2006, when he piloted Bug River – in what became a match race, with five of seven starters falling or pulling up – to edge Rosbrian by a head for trainer Regina Welsh and owner Northwoods Stable. Gracie rode just one more race that season before hanging up his tack to focus on his education at the University of Kentucky.

After several years in Kentucky learning the ropes of the bloodstock business, Gracie moved back to the Mid-Atlantic. Now at the helm of his own business, Gracie Bloodstock, he preps yearlings for sales at his Marshall, Va., base and travels up and down the East Coast to monitor the progress of clients’ horses.

But in 2018 it became clear: he missed the game.

“My first hunter was an old timber horse,” he says. “Two old bows, his legs were a mess, but I still think he’s the best horse I’ve ever ridden. He got me hooked. You don’t forget that feeling.”

Gracie rang up a few old friends and started riding again. He finished fifth in the 2020 Pennsylvania Hunt Cup on Kinross Farm’s Just Wait And See, his best stakes result since returning to the tack. This year, he’ll have the ride for the Richard Valentine trainee’s first Maryland Hunt Cup start April 24.

Snake Hill weaves, wanders and climbs as we trudge along. Past the Goodstone Farm entrance and up the hill. Middleton’s cattle chute looms at the top. Summit and descend, onward toward Benton, where retired hurdler Baltic Shore looks up from his round bale. Startled cyclists and curious horses converge. We break gait to let the traffic clear.

My watch announces the 2-mile mark as we pass Pot House Road. The Huntland cattle bellow and bawl. A stock trailer bounces past. ‘Turn around at Sean’s driveway?’ We agree.

Like amateurs in other sports, amateur jockeys are not paid to ride and cannot accept a share of any prize money. But for Gracie, a love for the game is enough.

“I don’t ride because I have to,” he says. “I do it because I enjoy it.”

Back the way we came. Our steps remembered by the damp gravel-and-stonedust road. Up the kennel driveway, I stop my watch as it ticks just past the 4 1/2-mile mark.

We take a breather in my barn aisle.

“I’ll keep riding for as long as I enjoy it,” Gracie says as he scratches the plain, broad forehead of a Lemon Drop Kid gelding. “That day will come, but I hope to get in a few more Hunt Cups first.”

Gracie leans against a stall door, grips a blanket bar, and thinks for a moment.

“Some really good horsemen passed on a good way of life to me,” he says. “That’s what’s important.”