Story and photo by Kerry Phelps Dale

Jim Herbert figures he puts about 500 hours into planning and executing the signature event of Christmas in Middleburg—the Christmas Parade, an annual occurrence since 1979. 

Since 2001, Jim has volunteered to help put the festive parade on. In 2010, he took over the management as parade organizer. It’s an all-volunteer event, but Jim plans to shift some duties to a paid part-time staff as the parade has grown to be too much to ask of volunteers. 

What started as about 40 floats parading before 2,500-3,000 spectators has grown to include approximately 80 elements stretching 1.5 miles long and lasting around 75 minutes start to finish. Crowd estimates have soared to 17,500 or more.

It’s a big day in Middleburg and the parade is the culmination of family friendly events starting with The Hunt Review and children activities running up to the 2 p.m. parade. Christmas in Middleburg consists of several events and activities starting with the Friday-Oh Holy Night tree lighting and ending with Foxcroft School’s live animal Nativity Pageant. 

There are food trucks to help with the restaurants’ overflow and the retail shops welcome the surge of business. One year one of the shops had the smell of fresh baked cookies wafting out into the streets through their open doors. It took one whiff and the entire pack of hounds bolted the parade and filed into the shop as one, following their noses to the only scent they had. “It took a while for the huntsman to get control of his hounds,” he recalls.

Organizing the parade is right in Jim’s wheelhouse. The Fauquier County native spent much of his career in international event management and marketing of trade shows. His goals for the parade and Christmas in Middleburg speak of his experience and interest in economic development. The parade’s impact reaches past the Christmas season and beyond the day’s attendance and revenues.

“It’s the biggest retail day of the year,” says Jim. But that’s just the beginning.  Jim figures that if you put Middleburg’s heart and soul out there for all to see—the horses, the schools, the library, the corgi’s, the super popular local Charros and high school bands—the visitors will come back. And they’ll tell others of the small town with a big heart. 

When Santa, the star of the parade, flies back to the North Pole and all of the evidence of the town’s biggest show is cleaned up and Middleburg’s quiet charm is restored, Jim settles into the Christmas spirit with his wife, Stewart, their two adult children and two grandchildren. ML

This article first appeared in the December 2019 issue of Middleburg Life.