Holiday Shopping Fun in the Washington, DC Area

For over two decades a group of gal pals and I have gathered in early December for an annual girls shopping weekend. We have shopped until we dropped in cities from coast to coast. This year was our second one in a row in the Washington, D.C. area since one of our friends lives in Haymarket, Virginia. From seeing the National Christmas Tree to the charming historic towns decked out with garlands and wreaths, the Mid-Atlantic Region is magical during the holidays. Here are some festive stops in and near D.C. that are fun any time of the year.     

But First…Wine 

In the hills of Virginia is a wine region that’s feels more like Tuscany or Bordeaux than right outside of Washington, D.C. Growing grapes and making wine has been happening in Virginia since the colonial era starting with the Jamestown settlement in 1607. Loudoun County alone has more than 50 wineries. Stone Tower Winery is about 30 minutes from Dulles International Airport. If you land midday like we did, head there for a wine tasting and delightful lunch atop Hogback Mountain. Stone Tower’s Sauvignon blanc pairs beautifully with their wood-fired margarita pizza. They have two tasting rooms. Both the Harvest Barn and Tower View Tasting Room have panoramic views of the pastoral 300-acre estate. During the holidays you can book Pancakes with Santa for 2-8 people. You can enjoy their lovely terrace in the winter by booking a wine flight tasting in one of several cozy ski gondolas. We hired a driver well in advance of trip, so all 8 of us could participate in holiday merriment and we didn’t have to worry about driving or parking during our shopping weekend. Our next stop was Greenhill Vineyards where they cultivate European varietals like chenin blanc and cabernet franc. It’s been a working farm since 1762 and is one of the oldest vineyards in Northern Virginia. While sipping wine, we enjoyed a stunning sunset from the expansive porch of their tasting room. Following our afternoon of wine tasting, we retreated to our friend’s home in Haymarket for a catered dinner and gift exchange. Doing this shopping trip for over two decades, we’ve found a low-key dinner is best for the first night of our 4 days together. For more about the wine region, read Virginia is for Lovers…and Lovers of Wine in Washington D.C.’s Wine Country.  

Strolling and Shopping in Middleburg 

Donning our holiday sweaters, we headed to Middleburg for a Friday of leisurely shopping. Surrounded by breathtakingly beautiful horse farms, this quaint town established in 1787 is known as the “Nation’s Horse and Hunt Capital.” Washington Street is the prime shopping street. It’s lined with charming shops and restaurants housed in quintessential stone and brick Virginia homes and buildings.  

We started at Lou Lou, a cute boutique with fun and trendy finds. From its signature candles to high-end unique items for the home, we perused Crème de la Crème for a while. If you’re a fan of French and Italian inspired items like this group of savvy travelers, you’ll enjoy the curated collections in this store. Don’t miss the book nook near the register, as it’s filled with thoughtful cards and intriguing books. For clothes, pop into The Lucky Knot, Zest Clothing & Company and Tully Rector. You’ll find an array of European ornaments and items in The Christmas Sleigh.  

Our pick for lunch was the lively King Street Oyster Bar. The blue crab dip, lobster cobb salad and fish and chips must eats. My favorite shop is the one we went to right after lunch. Brick and Mortar Mercantile has fun items with sayings guaranteed to make you laugh to handcrafted feather bowties and earrings. I made my big purchase of the trip and gifted myself a pair of the Brackish statement earrings. From there we headed to the PLAYroom. It’s a fabulous small town toy store overflowing with toys, games, puzzles and more. My friend Christy and I opted to head to happy hour at Tremolo, a lovely coffee and wine bar with a modern vibe. While sipping our Sancerre wine, we noshed on their four onion dip and chips. I tried to get the recipe, but they’re keeping it a secret. While we were sipping, the rest of our crew made a last shopping stop in The Christmas Shop at Emmanuel Episcopal Church built in 1842. The pop-up shopping experience has been an annual tradition at the church since 1948. It’s a great way to pick up some unique artisan finds. It’s shopping for a cause as a portion of proceeds is donated to several local nonprofits. 

Five-Star Dining Experience 

As the first destination resort in the Washington D.C. area, Salamander Middleburg is a 340-acre five-star resort and spa nestled in the heart of Virginia’s horse and wine country. It’s extraordinary when it is decked out for holidays. While a luxurious stay would be spectacular, you can also enjoy a taste of the Salamander’s five-star treatment with dinner at Harrimans Grill. We got to the Salamander in time to have pre-dinner cocktails from the Gold Cup Wine Bar, which we enjoyed by one of the fireplaces and stunning Christmas tree in the expansive lobby. Harrimans Grill is consistently excellent with top-notch service. A fabulous starter is the local greens salad topped with Virginia peanuts. I went for the honeynut squash agnolotti pasta dish topped with feta, sour cherries and pine nuts, and it was divine. Save room for dessert as their offerings are sinfully delicious.   

Holiday Cheer in Alexandria and D.C. 

Walk the historic streets of Old Town Alexandria in December for some festive fun. The nationally designated historic district is along the Potomac River waterfront. King Street Mile is lined with beautiful historic brick buildings filled with mainly independent businesses. Near the waterfront, King Street is a pedestrian zone with plenty of room to eat, drink and be merry while you shop without having to dodge cars. She’s Unique is a tiny shop filled with dainty jewelry pieces at reasonable prices. For a cute boutique with affordable chic, trendy and fun pieces, stop in 3 Sisters. The Market Square Shop is packed with everything from fabric by the yard to cocktail napkins to antique silver. For wrapping necessities, cute cards and stocking stuffers brave the crowds in Paper Source. Our favorite find was Twist Boutique just off King Street on North Fairfax Street across from Market Square. It’s a twist on a consignment shop with high-end designer pieces like Prada and Louis Vuitton, vintage finds and great gifts. After a couple of hours of shopping we enjoyed a leisurely lunch at Mia’s Italian Kitchen. Thankfully we had a reservation because this lively eatery was packed with people devouring their house made pastas and brick oven pan pizzas.   

For the afternoon, we headed to the D.C. Downtown Holiday Market. The annual outdoor shopping village pops up mid-November and runs through right before Christmas. The market covers two blocks in front of the Smithsonian American Art Museum and National Portrait Gallery. The tents are filled with artisan wares and unique gifts. On a Saturday afternoon the artisan stalls were bustling. Migue’s Mini Donuts must be delicious because there was a huge line for those sweet treats. After making the rounds in the market, we wandered into Dirty Habit in Penn Quarter. The courtyard bar was filled with folks in festive attire, which made for fun people watching while sipping cocktails. For dinner we had reservations at Old Ebbitt Grill. Across from the U.S. Treasury and close to the White House, the restaurant was established in 1856 and is dubbed “the oldest saloon in Washington.” They’re known for their seafood, especially oysters. I went for the jumbo lump crab cake with tons of crab and very little filler. I swapped out the coleslaw for the autumn market salad, which was a stellar choice.  

Monuments by Night 

After dinner we went on a private evening tour of the monuments with Continental City Tours. Our guide and owner of the company, Victor was a wealth of knowledge during our tour that started at The White House. At our next stop, we were wowed by twinkling colorful lights of the U.S. Capitol Christmas tree on the West Lawn. We went on to get incredible views of the Washington Monument and Jefferson Memorial. We made poignant stops at the World War II Memorial and Martin Luther King, Jr. Memorial before ending our tour at the Vietnam Veterans Memorial, Korean War Veterans Memorial and Lincoln Memorial. As impressive as the monuments and memorials on the National Mall are during the day, they are even more striking illuminated at night.   

More Holiday Cheer to Put on Your List 

We had planned to spend Sunday in Leesburg, another historic town which puts on quite a show during the holidays. But Mother Nature had other plans with heavy downpours sending us indoors to shop at Tysons Corner. We did shop Leesburg the year before and loved its downtown filled with cafes, boutiques and home décor shops. One shop filled with antique finds not to miss is The Lucketts Holiday House, an over-the-top holiday wonderland. 

 If you have more time in the D.C. area, enjoy Season’s Greenings for free at the U.S. Botanic Garden. It typically runs from Thanksgiving Day to New Year’s Day. Learn about 18th-century holiday traditions at Mount Vernon as you visit George Washington’s estate by candlelight. Tickets are required for the special tour on Friday and Saturday nights between Thanksgiving and Christmas. A big holiday draw for a lot of people is the National Christmas Tree in the President’s Park on the White House Ellipse. The 2023 tree is a 40-foot-tall Norway spruce from the Monongahela National Forest in West Virginia. The 100-year tradition of the National Christmas Tree Lighting Ceremony started with President Calvin Coolidge. On Christmas Eve in 1923, he lit a 48-foot Balsam Fir from Vermont decorated with 2,500 red, green and white electric bulbs. Another interesting tidbit about the National Christmas Tree is it’s surrounded by 58 smaller trees. They represent the 50 states, 5 territories, District of Columbia and two schools managed by the Department of the Interior’s Bureau of Indian Education and the Department of Defense Education Activity and are decorated with handmade ornaments by children in each. The National Christmas Tree is typically lit in late November or early December through January 1st. The lights are turned on around sunset each evening and turned off at 10 pm Sunday-Thursday and 11 pm on Friday and Saturday. 

While the Washington, D.C. area is an unexpected destination for a girls shopping trip, we found it to be filled with festive fun while enjoying bits of history, wine, food and fabulous boutiques, galleries and pop-up artisan stalls. The holidays are a magical time to see our nation’s Capital and explore some of the historic town offerings nearby.  

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