One of the beautiful things about Winchester VA is that it is an easy day trip from so many places including Washington DC, Annapolis MD, Fredericksburg VA, Deep Creek MD, West Virginia, heck, even Pittsburgh PA! The perfect location for a girls getaway whether you are celebrating a milestone like an upcoming wedding or just need to catch up with your sisters or favorite college roommates. Winchester is not only centrally located, but it is filled with delightful shops, dining experiences, and outdoor activities. So let’s put together a perfect weekend in Winchester!
Friday Day 1 – Check into the George Washington Hotel, and then take a quick break half a block up at Winchester Brew Works for a tasting or pint. Owners Bonnie and Holly will probably be hanging around and what better way to start a girls weekend than at a female owned brewery!
Your evening arrival will probably leave you wanting to relax to some entertainment while catching a bite to eat. Depending on how energized you feel you can catch a show and meal at Bright Box which hosts comedians, musicians, drag shows, films, and more throughout the weekend while serving light fare and drinks. Or maybe you are looking for a deeper appreciation of the south and more laid back environment? Head to Sweet Nola’s for New Orleans inspired southern food with a twist, alongside sweet jazz or live music. Our favorite? The Gumbo of course, but don’t miss the sweet potato fries sprinkled with confectioner’s sugar, yum!
Saturday Day 2 – Choose from a slow morning start with a quick swim in the GW pool or a massage at Sumaj, or venture out for a hike up Bears Den. Just outside of Winchester it’s a quick easy hike with fantastic views where you can sit on the rocks and enjoy conversation together!
Head back into the city for an afternoon Winchester Food Tour. You’ll get to know more about Winchester’s history and fun stories, while sampling delicious food from 5-6 unique Old Town Winchester restaurants. Finish the day with some shopping at Kimberly’s, Scarpa Alta, Simply Charming and Handworks Gallery.
Still hungry or need a nightcap? Winchester has a fantastic selection of International cuisine restaurants including Indian at Sona, Thai Winchester, La Nicoise Cafe, Awabi Japanese and Sushi, or Sexi Mexi Burritos. Or keep it light and enjoy an evening at Crush Wine Bar where you will fall in love with the intimate conversational seating areas. Browse the tapas menu, you are guaranteed to find something you must have! Our faves? Any of the smoked salmon, the brie and honey, and don’t miss the chocolate truffles with gold leaf as the perfect ending to your day.
Sunday Day 3 – Wind down your girls weekend with a visit to the Museum of the Shenandoah Valley. Yes, there are historical exhibits, but even if you aren’t into history spend some time in the ever changing art exhibits, expansive gardens inspired by Japanese tea houses and bamboo fields, walk through the Glen Burnie house (make sure you don’t miss the ballroom!) and Pink Pavilion (the perfect spot for a group photo!), and explore the upcoming trails that are currently being installed. Check their calendar for other special events as well such as music nights and even theater in the gardens. If you have time before leaving we suggest hitting one of the local vineyards for live music and a tasting. We recommend James Charles for a more modern atmosphere or Valerie Hill if haunted wineries are more your style!