From left to right, eight-year-old Evie Keys, Santa Claus, nine-year-old Michael Keys and Shepherdstown resident Cara Keys pose together for a photograph on Saturday. Photo by Tabitha Johnston

SHEPHERDSTOWN — Over his 21 years of portraying Santa Claus at Christmas events throughout Shepherdstown, Mark “Jimmy” Crain has never lost his love for the holiday season. Even, in spite of the difficulties that can arise while playing the role.

“There’s this age — maybe two or three — where children know who Santa is, but when they see him for the first time they always start to cry. The answer is always to tell their parents, ‘Don’t worry. Next year they’ll be fine and will have a list,'” Crain said. “And that’s always the case.”

After that, they may no longer be overwhelmed by the presence of Santa Claus, but they can still react strongly to being in his presence again.

“It can be challenging to get some of the children to speak, as well as challenging to try to get some of the children to stop speaking — some of them have the longest lists. They can’t stop speaking,” Crain said, chuckling.

Understanding what they are asking for can also prove a challenge, as new toys come out every year. Crain said he makes a point to familiarize himself with them, to ensure his portrayal remains believable to children.

Left to right, Boonsboro, Md. residents Heidi Bodenheimer, Julie Seabright, Holly Davis and Beth Ridgely take a moment for a photograph with Santa Claus, in the middle of their shopping day in downtown Shepherdstown on Saturday. Photo by Tabitha Johnston

“Trying to stay up with what some of the newer things are is important. I try to pay attention to the ads on TV, just so I understand what they’ll be asking for,” Crain said. “Many of the newer toys have long, long names to them, like a super special plushie or whatever.”

He noted that he is always pleased when children ask for gifts that promote learning.

“There’s always kids who ask for books or LEGOs or craft supplies — I like to encourage those,” he said.

Another thing he has enjoyed over the years has been connecting with people, even after they have stopped believing in Santa Claus.

“There’s usually a group of older kids — high school kids or something, sometimes — who will come in after all of the younger children have had their pictures taken,” Crain said, mentioning this regularly happens at the Christmas tree lighting ceremony in Shepherdstown. “It’s fun, because they just want their picture taken and you can joke with them a little bit more about stuff — all good, Christmas-appropriate stuff like, ‘Behave and get your schoolwork done.'”

Something similar tends to takes place at the free, annual Christmas dinner at the Shepherdstown Volunteer Fire Department, which was held on Sunday afternoon.

“A lot of times at the fire department, a lot of the older ladies come over toward the end of the event and want to sit on Santa’s lap. They come over and ask for a man or ask for a car. I always tell them, ‘I can’t help you with the Escalade — a matchbox car is the best I can do,’ and they laugh and we have a good time,” Crain said.

He gives a similar answer to young children, when asked for gifts that might prove problematic for him to promise.

“You always get the kids that want a puppy or a kitty or something else,” Crain said. “You can tell that the parents are cringing in the background, so I always say, ‘Reindeer don’t like live animals on the sleigh. But what about a stuffed animal? What color cat would you like — a black-and-white cat? If I was to get you a nice stuffed puppy, what kind would you like — a golden retriever or German shepherd?’ It’s quite plausible, to blame it on the reindeer.”

The greatest challenge, for Crain, has been learning how to respond when he is given an impossible request that must be taken seriously.

“There are kids who come up and say, ‘My dad’s sick’ or ‘My mom’s sick’ or ‘My brother’s sick’ and just want them to be better. Those are tough, because you know those are serious issues, in most cases, that you can’t do anything about,” Crain said. “I do my best to handle them with care.”

As he looks back on his long-held volunteer role, Crain said he is thankful for the opportunities he has had to touch the hearts of those he has encountered as Santa Claus and to bring a little Christmas magic to their holiday seasons.

“It has been a rewarding experience, in spite of the challenges,” Crain said, noting this was his final year in the role in Shepherdstown. “It has been enjoyable.”