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Shepherd family to pass on Christmas in Shepherdstown torch

By Tabitha Johnston - Chronicle Staff | Nov 26, 2025

Shepherd

SHEPHERDSTOWN — This will be the last Christmas in Shepherdstown overseen by the Shepherd family and its matriarch, Judy Shepherd, after three decades at the reigns.

It will be quite a change for the town, as it will mean that next year will be the first ever in which a Christmas in Shepherdstown will be celebrated without a Shepherd at the helm.

“This year will be our swan song. We have certainly been doing it for a long time,” Judy said. “My family and I have done the whole thing for the past 35 years, with the help of the Shepherdstown Rotary Club — God bless the Rotary for putting up the tree each year and putting the lights on it!”

The idea for Christmas in Shepherdstown and its kickoff celebration was developed by two Shepherdstown business owners, Jan Bender and Jo Ann Cartley. With their two shops being in the same building along German Street — Bender’s was a high-end home decor shop called The Village Green and Cartley’s was a high-end women’s dress shop — the pair regularly chatted together about business and the town.

“They decided that they were going to create a kickoff to the holiday season that would celebrate Shepherdstown and its history,” Judy said. “So they had a play and all of the founding families of the town — of which I am from one — were invited to it.”

That first celebration focused on the town’s English history, by incorporating a number of English traditions, including a stand in front of the Market House with roasted chestnuts, and having appearances from Santa Claus, Mrs. Claus and Ebenezer Scrooge, the main character from the classic novel by Charles Dickens, “A Christmas Carol.” It also featured young children like Judy’s at-the-time five-year-old son Chris, who is now 41-years-old, playing a pickpocket who, instead of taking things from people, would put nice surprises in their pockets.

In the years since, the celebration has adopted various changes, in line with the evolving nature of Christmas traditions.

“We introduced the Grinch several years ago, as he is the modern counterpart to Ebenezer Scrooge. The kids started to gravitate to that character, so we slowly but surely changed it over — although, we have recently brought Scrooge back to the celebration last year,” Judy said, referring to the central character in Dr. Seuss’ children’s book, “How the Grinch Stole Christmas!”

With the inclusion of the Grinch, Judy decided to also add a cohort of the Grinch’s neighbors — the Who’s — to the celebration. And, when she portrays Mrs. Claus at the beginning of the event, sitting in a rocking chair on the lawn of McMurran Hall, she always reads that story, along with a picture book featuring Clement-Clarke Moore’s classic poem, “The Night Before Christmas.”

Other additions to the celebration, which will be held again this year from 5-9 p.m. the day after Thanksgiving, have been: the bonfire and s’mores offered in front of Town Hall by the Shepherdstown Volunteer Fire Department; the Shepherdstown Kiwanis Club’s chili cookoff in the War Memorial Building from 4-7 p.m.; and the driving of Santa Claus in a fire truck down German Street to McMurran Hall. It is followed from 12-3 p.m. the next day, by the Who-liday Celebration in the War Memorial Building, featuring a free magic show, Christmas treats and more children’s activities.

“This has been a gift that my family has always enjoyed giving the town,” Judy said, mentioning her children have all grown up helping with the holiday events. “My kids are all grown now. I have three littles and a 23-year-old grandson. It’s time to pass on the torch.”

The props and costumes used for the kickoff weekend to Christmas in Shepherdstown will be bequeathed to the future organizer of the event, Experience Shepherdstown.