Christmas in Middleburg November 5, 2026 Picture the scene: dozens of scarlet-jacketed riders, packs of pure-bred foxhounds, vintage horse-drawn carriages, a 1.5-mile-long procession of floats, firetrucks, drummers, bagpipers, bikers on Harleys… An hour west of Washington, D.C., historic Middleburg, America’s horse and hunt capital, is gorgeous all year round but it comes into its own in December with the traditional Christmas in Middleburg parade and festivities on the first weekend of the month. Friday: Tree Lighting Ceremony and Carols Celebrations actually start on the Friday before with the Oh Holy Night! Tree Lighting Ceremony and Carols in the garden of the Middleburg Museum in the heart of town. Nearby restaurants and bars are buzzing while kids sip hot chocolate from local shops. Before the lighting, get dinner or browse the boutiques on and around Washington Street. Saturday: Hunt Review and Christmas Parade On Saturday, the fun kicks off at 8 a.m. when the Middleburg Charter School PTO hosts its annual Breakfast with Santa. Little ones get to meet and take photos with Santa and Mrs. Claus while parents and older siblings enjoy a hearty family-style breakfast. Soon it’s time for the parades! Eleven a.m. sees the start of the Middleburg Hunt & Hounds Review where hounds and dazzling mounted foxhunt riders of the Middleburg Hunt parade down two-lane Washington Street. The pavement is packed with a festive crowd so come early for a good view or book a streetside table at lively King Street Oyster Bar, where you can toast it all with a champagne glass in hand. The Christmas Parade follows at 2 p.m. where half the town’s residents participate while the other half cheers them on. After that it’s time to get into the spirit of it all at one of the many wineries, breweries, restaurants and bars in and around town. Sunday: Christmas Pageant at Foxcroft School But the weekend is not over. To come full circle, the following day – Sunday 2 p.m. – the new girls of the aforementioned Foxcroft School host their traditional Christmas Pageant, a dazzling rendition of the Nativity featuring live animals, music and a manger. Share on FacebookTweetFollow usSave