Experience a Magical Christmas Getaway in Leesburg, Virginia

This authentic small town in Virginia is known for having plenty of holiday cheer.

Given its proximity to Washington, D.C., and a busy international airport like Dulles, you'd expect Leesburg to feel like a modern suburb on the verge of sprawl, but just the opposite is true. Locals and travelers enjoy an authentic small-town experience as they stroll cobbled sidewalks of the historic district or jostle down dirt roads to an area vineyard. And at Christmastime, the whole town gets into the holiday spirit.

Established in 1758, Leesburg lies in northern Virginia, along the Potomac River and the foothills of the Blue Ridge Mountains, which you can see on its western horizon. Rolling hills welcome visitors into town as farmland and family-owned wineries begin to pepper the landscape. Over time, this once-quiet hamlet has blossomed into a dynamic and desirable area, the seat of the third most populated county in Virginia (Loudoun) as well as a commuter hub for, and weekend escape from, D.C. Today, Leesburg is an eclectic mix of old and new, high tech and rural, as locals fiercely cling to its distinctive historic character and authenticity.

The Old Lucketts Store
Helen Norman

Shop in a Christmas Wonderland

Much of the hometown appeal centers around the Leesburg Arts & Cultural District, including King, Market, and Loudoun Streets. The town encourages residents and visitors to meander around on the first Friday of the month, when many restaurants and shops stay open until 9 p.m. or later to host live music, lectures, special exhibits, and wine tastings.

Drawn to the district's walkability, Nicole Morgenthau wanted to build a center for the maker community, a place where, she says, "They feel connected and gather with a common interest, with people different from themselves." Set in a circa-1790 three-story retail building, Finch Knitting + Sewing Studio on the corner of Wirt and Loudoun Streets provides locally sourced yarns, along with high-end fiber supplies from Quince & Co. and other socially responsible establishments that follow the "farm-to-needle" philosophy. Classrooms on the first floor serve beginner to experienced sewers while knitting groups adopt sofas and cozy nooks on the second level. During the holidays, Morgenthau decorates the exterior of her studio to look like a giant gift box.

Finch Knitting and Sewing Studio in Leesburg VA
Nicole Morgenthau owns Finch Knitting + Sewing Studio, which supports socially responsible,. Helen Norman

A relative newcomer to the historic-district retail scene, 27 South Interiors sets a high bar for providing stylish and comfortable home furnishings. Co-owners Carolyn and Nick McCarter opened their three-story shop after a successful run selling vintage furniture out of local consignment stores. "We intentionally designed it like a home," says Carolyn. "Everything is selected to create a very curated look."

The McCarters celebrate with a tall Christmas tree, along with ornaments showcased on a large branch suspended above the front of the store. The branch has become a town conversation piece and now changes with the seasons, from bare winter limbs to budding flowers in spring. Carolyn tries to create more traditions to encourage the downtown revival. "Historic Leesburg is coming into its own again, and we want to take part," she says. "Our King Street storefront is a great tool to connect with everyone and help it grow."

27 South Interiors in Leesburg, VA
For holiday flair, check out all the festive decor at 27 South Interiors owned by Carolyn and Nick McCarter. Helen Norman

"Christmas in Leesburg really does bring out the best in our community," says Tammi Ketterman, co-owner of Ketterman's Jewelers. Since 1988, this fine-jewelry shop has welcomed shoppers while giving back to associates, customers, and residents. Ketterman does not follow suit with those retailers who start decorating for Christmas in October.

"We feel strongly that Thanksgiving needs to be celebrated, not overshadowed," Ketterman says. "So we wait until the last Saturday before Thanksgiving and gather the staff and their families for a meal. Then, after dinner, we break out the decorations, and the store is transformed into a Christmas wonderland." Slices of her delicious homemade rum cake are served every day from Thanksgiving until New Year's.

People in Leesburg appreciate tradition and continuity. Owner Anita Henry of Rouge Spa & Boutique creates custom perfumes, body sprays, and bath bombs in a variety of seasonal fragrances. Kids are welcome too. During two-plus decades at the same King Street storefront, Henry has helped a generation of youngsters she calls "Rouge babies" find the perfect presents for their parents.

The Old Lucketts Store Owners in Leesburg, VA
Amy Whyte and Suzanne Eblen (from left) bring on the cheer at Lucketts which fills with over-the-top decorating at Christmastime. Helen Norman

The Old Lucketts Store on Lucketts Road is not a place you can breeze through. You'll need time to wander what was originally an 1879 general store and is now a three-story furnishings and decor emporium—along with numerous outbuildings holding everything from architectural salvage to garden goods. Owner Suzanne Eblen opened the store in 1996. She and business partner Amy Whyte have developed a devoted following with their signature style, which includes lots of pieces that are new but look vintage.

For the holidays, the two of them decorate to a degree that even Eblen describes as "level 10 bonkers." The large painted murals on exterior walls make ideal backdrops for taking family photos. Greenery, ornaments, and other holiday swag embellish just about everything from the ground to the gutters. One of the highlights of the Lucketts property is Eblen and Whyte's extraordinarily popular Design House, a 100-year-old home with each of the spaces (including the bathroom) furnished to suit its original intended purpose and designed around its own theme. It has morphed from a pop-in weekend shopping space to a ticketed event during the first 12 days of November. Eblen and Whyte have to shut down the house for two months before the holiday opening to transform the place.

The Wine Kitchen in Leesburg, VA
Executive chef Tim Rowley of The Wine Kitchen changes his menu seasonally. Helen Norman

Eat, Drink, & Be Merry

You probably won't make it through all the shops downtown before you have worked up an appetite. The Wine Kitchen serves inventive meals with an emphasis on both local and organic ingredients and a menu that changes seasonally–and sometimes more frequently, depending on availability. "December is always an interesting time for us," says owner Jason Miller. "The area farmers are getting some much-needed rest after a long fall harvest. We use a lot of root veggies, but instead of being boring, we get creative."

Look for a beet-and-citrus salad or seared duck breasts and confit on their winter menu. There's good wine here, but consider ordering a comforting homemade eggnog that's kicked up with spirits from nearby Catoctin Creek Distilling Company. The Bubble-icious sparkling wine flight stays on their menu year-round. They also have 10 pre-made flights that feature red wines, white wines, or special themes like "The Hills of Italy" or "Working for the Weekend."

Shoe's Cup and Cork in Leesburg, VA
Shoe's Cup & Cork has a hot chocolate flight to warm you up. Helen Norman

Completed circa 1880, the building that currently houses Shoe's Cup & Cork was previously a post office, an auto showroom, and then a shoe-repair store. The small, cozy restaurant has a secret garden and bocce court out back as well as a speakeasy-inspired poker room upstairs. Shoe's offers a hot chocolate flight, perfect for a chilly evening.

At the corner of Loudon and King, Señor Ramon Taqueria's Mexican street food hits the spot. Don't overlook sides like the popular corn nuggets and tasty empanadas. Across the street, Delirium Café features Belgian-style food and all types of local and holiday-themed brews such as Gingerbread Stout. The group of cafes started in Brussels, but Leesburg has the first U.S. location.

On East Market Street, Melt Gourmet Cheeseburgers was voted the state's most delicious burger joint and has an array of toppings for the classic beef patty (not to mention bison, crab, tuna, lamb, and veggie versions).

A few miles north at the intersection on Route 657, Roots 657 looks like one of the modern metal-roofed barns peppering many of the country roads in this part of Virginia. Inside, half the space is dedicated to local crafts, foods, wines, and beer while the other section is a casual, family-style restaurant. (The Maryland Crab and Corn Soup and Signature Brisket Sandwich stay on the menu for good reason.)

Sip Local Wines

Loudoun has more wineries than any other county in Virginia, and the rolling hills surrounding Leesburg provide a stunning setting for 300-acre Stone Tower Winery offering expansive views of Bull Run and the Blue Ridge Mountains. Holidays at work are especially sentimental for Lacey Sautter, vice president of the second-generation, family-owned winery. Garland and swag lights drape over terraces and porches to add a touch of drama, but it's the dozens of trees adorned with ornaments that kindle memories. Wine lovers come here for the Porton, which is available only upon request. The port-style sipper is made from Virginia-native Norton grapes and fortified with locally made Catoctin Creek brandy. A food menu is available at the harvest barn, which is also family and dog friendly.

Re-Experience History

The Loudoun Museum serves as a repository for the county's history, from the early days of the republic to the formation of the local wine industry, and includes an adjacent circa-1760 log cabin. You can see fine 19th-century architecture via tours through a few of Leesburg's restored historic homes, including Dodona Manor, former home of Nobel Peace Prize winner Gen. George C. Marshall, architect of the post-World War II Marshall Plan. Drive a few miles north of downtown to the Davis Mansion at Morven Park, a former Virginia governor's estate with an international equestrian center, and don't miss Christmas at Oatlands, which features self-guided and candlelight tours around Oatlands Historic House & Gardens.

Stay in Luxury

Large families can stay right on the Oatlands property at the six-bedroom historic Inn at Oatlands Hamlet. Landsdowne Resort, a modern, full-service retreat, has everything from upscale rooms to 45 holes of golf, a spa, and several other luxury amenities. For an authentic experience on a Loudoun County farmstead, stay at Stone Gables Bed & Breakfast, a home converted from a circa-1823 stone gable barn, set within 10 acres of verdant countryside.

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