Leesburg, Virginia, is an Idyllic Winter Escape
By: Megan Williams
Imagine it: It’s a few weeks until Christmas and you’re in desperate need of a getaway. Your shopping list is complete, the paper full of crossed off names and gift ideas looking worn since you meticulously crafted it months ago. Your freezer is stocked with sweet potato casserole, sourdough bread, and the turkey you snagged on sale—all ready to be pulled out for the big family dinner. The stockings are hung, the ornaments are perfectly placed, and your social calendar is filling by the minute.
Then, a light bulb moment. What you need most of all is a weekend away, filled with window shopping along cozy, evergreen-lined streets. You need a dim restaurant or two to tuck into with a glass of wine. You need the beauty and stillness of the holiday season without having to orchestrate every detail yourself. You need a trip to Leesburg, Virginia.
A Postcard-Worthy Town in Virginia Wine Country
In the heart of Loudoun County, Leesburg is a charming town that perfectly embodies the spirit of the holiday season. Just about an hour’s drive from Washington, D.C., this picturesque locale is surrounded by the rolling hills of Virginia’s wine country, making it an ideal escape for those seeking both relaxation and festive cheer. With its rich history, vibrant downtown, and stunning countryside, Leesburg invites visitors to slow down and savor the magic of Christmas.
Photo: Katey Jackson
As you stroll through downtown Leesburg, you’ll be enchanted by the historic buildings that line the streets, many of which date back to the 18th and 19th centuries. The town’s aesthetic is a delightful blend of quaint small-town charm and modern vibrancy. Cobblestone sidewalks are adorned with twinkling lights and seasonal decorations, creating a warm and inviting atmosphere. Boutique shops offer unique gifts, artisanal crafts, and local wines—perfect for finding that one-of-a-kind present for your loved ones. The aroma of freshly baked goods wafts from cozy cafes, while the sound of cheerful holiday music fills the air, inviting you to pause and soak in the festive spirit.
What makes Leesburg truly special is its sense of community and celebration. During the Christmas season, the town comes alive with events that highlight its rich heritage and festive spirit. You might find yourself enjoying a classic holiday parade, where local floats and marching bands fill the streets with cheer or attending a seasonal market featuring local artisans and delicious seasonal treats. There’s something undeniably heartwarming about mingling with locals, all while taking in the sights and sounds of the holidays.
Photo courtesy: Town of Leesburg, Photo Credit: Samantha Eisenhower
And do take the time to explore the surrounding Virginia wine country—which is celebrating its 40th anniversary as an acclaimed wine region. The region is renowned for its award-winning wineries and breathtaking landscapes, making it a perfect backdrop for a winter getaway. Spend an afternoon touring vineyards, sipping on rich red wines by the fireplace, and soaking in the beautiful scenery dusted with a hint of winter frost. Many wineries offer special holiday tastings and events, so you can experience the local flavors while getting into the festive spirit. If you prefer not to leave the comfort of Leesburg’s cozy downtown, most restaurants offer local and regional wine by the glass or bottle. Not to mention, Echelon Wine Bar is a downtown tasting room for the award-winning Vineyards and Winery at Lost Creek, which makes 100 percent Loudoun County wine from grapes grown in their Meridian Ridge vineyard.
As the sun sets and the town glimmers with holiday lights, you can settle into one of Leesburg’s inviting restaurants. Whether you’re in the mood for a cozy pub or an elegant dining experience, you’ll find plenty of options that cater to your cravings. Enjoy a hearty meal paired with a glass of local wine and relish the warmth of good company.
For a truly magical evening, visit The Wine Kitchen, which runs right through the heart of downtown Leesburg on King Street. Set in a 1840s-era brick building, The Wine Kitchen boasts a seasonal, Italian-inspired menu that features local, seasonal food through the lens of fresh Italian cuisine. Its small footprint and dimly lit interior offer the perfect respite from winter’s chill. Forty wines by the glass and in tasting flights are also available to give you your first glimpse into what makes Loudoun County wine so magical.
Photo courtesy: Town of Leesburg
In Leesburg, the magic of Christmas is woven into the very fabric of the town, making it a perfect destination for a weekend getaway. Whether you’re shopping for gifts, savoring seasonal treats, or simply enjoying the beauty of the countryside, you’ll find that this charming town captures the essence of the holiday spirit, leaving you refreshed and filled with joy.
As you wrap up your weekend in Leesburg, let the spirit of the town linger long after you’ve packed your bags. Imagine carrying a piece of its charm with you—a handcrafted ornament from a local shop, a bottle of exquisite wine, or even the warmth of a shared laugh with new friends at a festive gathering. This town isn’t just a destination; it’s a reminder that the holiday season is about connection, community, and the simple joys that come from slowing down and savoring the moment. So, as you return to the hustle and bustle of your holiday preparations, take with you the essence of Leesburg: a spirit of warmth and togetherness that invites you to create your own cherished memories, one twinkling light at a time.
Leesburg Holiday Events You Won’t Want to Miss
- December 7: Annual Christmas tree lighting in the Town Square
- December 7 & 8: 34th Annual Leesburg Holiday Fine Arts and Crafts Show with more than 90 local artists, artisans, and crafters
- December 14: Annual Christmas parade down King Street, lined with boutiques and local restaurants, many of which are decorated for the season
- Throughout the season: Harry Potter and the Forbidden Forest at Morven Park, just outside the main historic streets
