Winterfest’s Brightest Light
Ray Shepherd just may be the most photographed man in the history of Ocean City.
For nearly two decades, he’s portrayed Santa Claus at Ocean City’s Winterfest of Lights, posing with countless fans for a treasured holiday portrait. When he first took the gig, people were still using Polaroids. Then the world moved on to digital point-and-shoot devices, and now, everyone captures — and shares — the moment with their smartphones.
“I don’t know how many people I’ve seen,” he said. “We’ve never really counted. People sometimes will come back a couple times a year. Thanksgiving time is the biggest... we’re pretty well swamped. I try to spend as much time with every kid that comes up. I don’t hurry them: ‘What do you want for Christmas?’”
What do you want, indeed. Ray said he doesn’t keep up with which toys are hot, so when the kids come in, “I learn about all the new toys, and I ask a lot of questions. It’s kind of hard to keep up with all the new stuff. I still have kids who want
Many kids are shy and unsure when they meet him, saying, “You’re not real.” “I say, ‘Well, let’s talk about it.’ Santa’s in your heart. I don’t discourage them from believing,” he said.
Santa Ray especially likes when parents grab him before meeting their kids, to share tidbits of personal information. Then, when they meet Santa, he seems to know — magically, — details about their life. “I blow their little minds,” he said with a grin.
It’s not always kids taking a seat in his lap. Four men in 18 years have made marriage proposals. Thankfully, all the ladies said yes. The grooms tend to run it by Ray first.
Back in 1999, Ray Shepherd was a 55-year-old copier salesman, with a side job at Winterfest, helping load visitors onto the holiday-lights tram. When a departing Santa had to be replaced, the town came to him and asked him if he’d take the job.
“It was hard when I started, because it was seven nights a week, six hours a night,” he recalled. “I still worked full-time until I was… I don’t know what year. I was 62 when I retired. I sold copiers and faxes. I worked every day, and I was doing Santa at night.”
Since then, his tenure at Winterfest has spanned four presidents, three popes, and 10 Olympic Games. He’s outlasted the Y2K scare, the rise of the Internet and the financial crisis. Remarkably, town officials report that Ray never missed a day of work or even called in sick.
He tries to keep a Santa image alive all year long, and it’s not always in the traditional red suit. People have him pose for photos with their pets. He visits medical clinics and local churches in character. He does a “Swim With Santa” event twice a year in Ocean Pines, where he puts on red swim trunks and jumps in the Sports Core pool alongside the kids.
Though he’s officially retired, he holds down a summer job mowing lawns at a local golf course (he calls his red tractor “my summer sleigh”), where golfers often recognize him and ask for photos.
Santa Ray grew up in Teaneck, NJ, and as a young man served in Vietnam as a Navy radioman. In 1965, he married a Delmarva girl, and together they raised three children and four grandkids.
Ray lost his wife this year to ovarian cancer. Now, at age 74, he’s fighting his own battle with Stage II colon cancer. Both his beard and his “bowlful of jelly” are thinner than they used to be.
“I don’t have any cancer in my body, but I’m going through chemo,” he said. “I haven’t lost any hair. I don’t think people are going to notice. I’ve always been up-front with the people in Ocean City, to keep them informed about what’s going on with me.
“I know at one point that they’re going to have to replace me,” he added, his voice breaking, “but it is what it is, right?”
Over all these years, what really means the world to Santa Ray is how the young kids he held in his lap for their first photos with Santa are now bringing back their own children to meet him.
“It makes me feel good,” he said. “It’s hard to put into words, because I’ve done this so long; it’s just a part of what I do. Even when I’m out, people tell me, ‘I’ll be good until December 25, and then you gotta visit me.’ This time of year, people start to recognize,” he says in a whisper, “There’s Santa!”
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