A Girlfriends Guide to Leesburg & Middleburg

3 Day Itinerary

Day 1

Start the trip to Loudoun County with a ladies luncheon at a downtown Leesburg institution. Named after a local Loudoun hero, Lightfoot Restaurant, originally built in 1888 as Peoples National Bank, is now a historic landmark and restored to its Romanesque Revival Style grandeur. It offers imaginative and artful cuisine in a beautiful historic atmosphere. It is the perfect stop to start a ladies weekend!

Walk off the calories at Leesburg Corner Premium Outlets, featuring designer stores at cut-rate costs or get in your shopping groove at Dulles Town Center. With over 125 stores, there is a shop to fit every style.

Channel your creative side at a Paint & Sip class at a local winery or studio. Follow an artist through a step-by-step guided class while enjoying your favorite beverages and snacks. Leave with a work of art to show off! 

Enjoy dinner at Tuscarora Mill. Known as "Tuskie’s" to locals, the restaurant has earned its reputation through its "authentically local" experience felt in the ambiance and décor, conveyed by the passionate staff and evident in the quality cuisine.

Leesburg, the county seat, has an ever-evolving downtown. With a seasonally-evolving pop-up bar, a recently-opened downtown rooftop hotspot at Cocina on Market, new nightlife hangouts, restaurants serving local spirits, beers and wines, it is the perfect place to spend the evening while enjoying the company of friends.

Enjoy home-away-from-home comforts at a lovely Loudoun bed & breakfast or resort for a two-night stay and rest up for the rest of your adventure!

Day 2

After breakfast, a morning of relaxation awaits. Get pampered at a local spa. Schedule a massage, get a manicure or pedicure, or try a new hairstyle. With several local spas, resort spas and salons, Loudoun County has plenty of pampering packages to treat yourself.

Nothing pairs with relaxation as well as chocolate. Visit one of Loudoun County’s newest favorites, The Conche. Passionately sourced and tastefully crafted, The Conche is a chocolate-themed restaurant, bar, chocolate boutique and chocolate lab from award-winning Chef/Owner Santosh Tiptur. Enjoy lunch at The Conche followed by a chocolate tasting, which showcases delicious chocolates to help decide which ones to take home!

Savor the view atop Hogback Mountain while enjoying a tasting at Stone Tower Winery. Boasting award-winning wine and breathtaking views, Stone Tower is highly regarded as one of Loudoun’s staples. After a tasting, sip vino on the patio, walk through the vines or visit the different tasting areas on property.

Head to dinner with a twist at Cookology-Recreational Culinary School, where the art of preparing dinner is part of the evening. Learn to make Beef Wellington or take part in an Iron Chef-style competition, where the ingredients are a mystery until you begin the challenge. If dessert is all you’re feeling, Cupcake Wars it is!

Located in this unique community of shopping, dining and culture, One Loudoun has become Loudoun County’s new downtown. Choose from one of several chic restaurants & bars, including Eddie Merlot’s, Sense of Thai, Cooperwood Tavern and many more. Visit a few or find a spot to spend the evening enjoying company.

Day 3

To kick off your last day in Loudoun, try the one-of-a-kind EquiSpective at the Salamander Resort and Spa. Out in the stables, experience this unique self-discovery program that unites horses and humans through a hands-on approach that puts visitors in the ring, communicating with the gentle creatures. Spend time in the nation’s horse and hunt capital, Middleburg. Named for being the halfway point between Winchester and Alexandria, Middleburg boasts a history heavily seated in the Civil War.

Grab lunch and spend some time exploring historic Middleburg, which is home to a plethora of charming shops and restaurants. Locals love Market Salamander, The Upper Crust, King Street Oyster Bar and The Red Fox Inn & Tavern.

Don't forget to hit the vineyards before heading home! Greenhill Winery and Vineyards, located just east of Middleburg, is a boutique destination winery home to a 4th generation Bordeaux winemaker, spectacular views of classic Virginia landscape and award-winning wines-one of which was placed in the 2016 OSCAR gift bags to select nominees! Just a bit further west and offering one of Loudoun County’s most spectacular views from atop the first peak of the Blue Ridge Mountains is Bluemont Vineyard. For dinner, try Bluemont's Chef's Table Tasting Experience — a four-course foodie experience that expertly pairs the freshest produce from the family farm, Great Country Farms, with some favorite wines.