For Hunt-and-Hound Festivities
location_on Middleburg
language Website

Head to this equestrian destination for a Christmas pulled from the preppy pages of a Ralph Lauren catalog. Restaurants and boutiques along Washington Street get dressed up with lights, bows, and garlands, while a slate of programming starts with a tree lighting on December 5. The festivities continue the next day at the Middleburg Hunt Review and Traditional Christmas Parade, where hounds scamper down the street alongside horses and riders, classic cars, and Santa Claus. Throughout December, Middleburg also puts on a series of Dickens-inspired events, with carolers, actors, and musicians bringing his classic holiday story to life.
Distance from DC: One hour.
For a Coastal Christmas
location_on St. Michaels
language Website

The main drag in this nautical Eastern Shore town is decorated with twinkle lights and Christmas motifs throughout December, though the charm gets dialed up from the 12th through the 14th. Activities include a gingerbread-house competition, a merry concert, and breakfast with Santa. On December 13, a procession with vintage cars and llamas moves down Talbot Street in the morning, but it’s a second parade at night that flexes the town’s location on the water: Boats are draped in lights, illuminating the harbor during the promenade. Between events, you can enjoy live music, food vendors, and carriage rides.
Distance from DC: An hour and a half.
For Festive Shopping
location_on Lewisburg, W. Va.
language Website

Stores along Washington Street get a holiday makeover, transforming this West Virginia town into a winter wonderland with glowing snowflakes and lights. Play Santa’s helper and pop into boutiques selling vintage wares, stocking stuffers, clothes, stationery, and more. There are also specials and discounts on select days during the holiday season. Santa visits nearly every weekend in December, but if you miss him, there’s a place to drop letters to the North Pole. The truly holiday-obsessed can book a room at the Greenbrier Resort in neighboring White Sulphur Springs, renowned for its elaborate decorations.
Distance from DC: Four hours.
For Dazzling Displays
location_on Leesburg
language Website

There’s something nostalgic about walking around a neighborhood to gawk at decked-out homes. Less than an hour from DC, Leesburg offers plentiful paths for admiring lights and over-the-top DIY visuals. Homeowners begin as early as mid-November, designing classic, intricate, and Griswold-esque masterpieces in neighborhoods such as Woodlea Hills and Lansdowne. Grab a hot drink and stroll the streets, picking out favorite displays. While waiting for the sun to set, stop at the kitschy Lucketts Holiday House, where every room of the 100-year-old farmhouse is outfitted in whimsical (and often vintage or retro) decor, all for sale November 6 through December 14.
Distance from DC: 45 minutes.
For a Polar Express Journey
location_on Staunton, Va.
language Website

Since its 2004 debut, the film The Polar Express has inspired dreams of a magical Christmas expedition. This quiet Shenandoah Valley town, home to the Virginia Scenic Railway, delivers. Staunton is the origin point for the Santa Express, a holiday train featuring decorations, seasonal treats, jolly music, and, of course, Saint Nick. This year, the railway is debuting “Holiday Spirits,” an adults-only experience with the same trimmings and treats, along with the option to order themed cocktails. Beyond the rails, look for stocking stuffers at the Saturday winter market and stop by Art for Gifts, a craft fair featuring work from more than 70 Virginia artisans.
Distance from DC: Three hours.
For an Old-Fashioned Holiday
location_on Williamsburg
language Website

Cannon fire to celebrate the season? It’s one of many historic traditions preserved in Colonial Williamsburg, where the group Fifes & Drums fills the streets with music and General and Lady Washington star in holiday reenactments. Walking tours provide insight into the era’s yuletide past while you take in the adornments. Mark your calendar for December 6, 13, and 20: On those Saturdays, the Grand Illumination takes place above the Capitol and Palace, filling the sky with fireworks, musket smoke, and, yes, cannon fire, all inspired by the Colonial era.
Distance from DC: Two and a half hours.
For Hallmark Vibes
location_on Berlin, Md.
language Website

The lovely town had its Hollywood moment in the 1999 movie Runaway Bride, but in December it’s like stepping into a Hallmark Channel film. On December 4, the Berlin Christmas Parade—the largest such parade on the Eastern Shore—features 80 floats, dancers, and firetrucks to rev up the crowd in anticipation of Santa’s arrival. Decorations and events continue throughout the month, with meet-and-greets at Kringle Kottage and a wintry farmers market for hot cocoa, crafts, and roasted chestnuts. Free carriage rides complete the rom-com fantasy.
Distance from DC: Two and a half hours.
This article appears in the November 2025 issue of Washingtonian.