There’s a place where Christmas feels like it gallops straight out of a storybook — and that place is Middleburg, Virginia. Each December, this historic town in the heart of Virginia's horse country transforms into a winter postcard filled with jingling sleigh bells, red-coated riders, and small-town warmth. For those who cherish tradition, equestrian charm, and timeless holiday spirit, Middleburg is nothing short of magical.
The Parade That Stops Time
The first weekend in December marks Middleburg’s legendary kickoff to the holiday season. On Saturday morning, the Middleburg Hunt Review takes center stage — dozens of riders dressed in scarlet coats parade through town on horseback, accompanied by a lively pack of hounds. This nod to the region’s foxhunting heritage sets the tone for the day. By afternoon, the main Christmas parade fills Washington Street with floats, marching bands, antique carriages, llamas, and of course, Santa himself arriving in equestrian style. The atmosphere is electric — festive, nostalgic, and deeply rooted in community tradition.
A Town Steeped in History
Founded in 1787, Middleburg is rich in early American history. Its preserved architecture and historical landmarks provide the perfect backdrop for a classic holiday setting. During the Civil War, Middleburg served as a strategic location and witnessed several cavalry skirmishes. In the 20th century, it became a favorite escape for First Lady Jacqueline Kennedy, who found peace and joy horseback riding through its countryside. Today, the town honors its past while celebrating the spirit of the season with candlelight tours, local performances, and centuries-old inns like the Red Fox Inn & Tavern, aglow with pine boughs and lanterns.
Holiday Experiences Beyond the Parade
December weekends in Middleburg are packed with carolers, carriage rides, Christmas markets, and cozy cocoa stands. Many shops stay open late for "Jingle in the Burg" festivities, offering warm drinks and festive discounts under twinkling lights. At nearby Salamander Resort, families can enjoy holiday brunches, cookie decorating, and even tubing when the snow cooperates. Local wineries offer seasonal tastings, and the National Sporting Library & Museum offers a peaceful spot to reflect and enjoy equestrian-themed art.
A Collectible Slice of Middleburg
No Christmas celebration is complete without a keepsake to remember it by — and one of the most enchanting tributes to Middleburg is captured in the beautiful collectible found here at The Christmas Sleigh. This exquisite hand-painted scene features Washington Street during parade day, complete with horses, hounds, and historic buildings cloaked in snow. Whether you're a longtime Middleburg visitor or simply a collector of charming holiday décor, this piece brings the warmth of the season home.
Explore Our Middleburg-Inspired Treasures
At The Christmas Sleigh, we’re proud to offer a curated collection of items that celebrate the spirit and scenery of Middleburg. From ornaments that capture horse-drawn sleighs and downtown shopfronts to hand-carved figurines reminiscent of local traditions, each piece is chosen to reflect the unique blend of elegance and rustic charm that makes Middleburg so beloved. Perfect as gifts or additions to your own décor, these pieces are timeless tributes to one of America’s most picturesque Christmas towns.
Plan Your Visit or Bring It Home
Whether you’re planning a trip to witness the parade in person or simply want to recreate the magic at home, Middleburg offers something truly special. It’s a place where the past and present mingle under garlands and lanterns, where horses and history meet holly and hearth. And even if you can’t stroll its cobbled streets this December, you can still experience its magic through the traditions, stories, and treasures shared at The Christmas Sleigh.
Sources: Middleburg Business & Professional Association, Garden & Gun Magazine, The Christmas Sleigh Collection