4+ Adults-Oriented Must-Dos in Winchester, Virginia

Winchester VA
Discover Winchester-Frederick County in the Shenandoah Valley.

By Hope S. Philbrick

My first impression of Winchester, Virginia: Don’t wait for a conference as an excuse to visit.

You can’t really get to know a place while sitting in a meeting room.

Fortunately, when I visited Winchester, Virginia for a conference, the organizers made certain to schedule time to get out and explore. One look around and I’d wished I’d have made it to the city sooner.

Founded in 1744, Winchester is the oldest city west of the Blue Ridge Mountains. Located at the northern end of the Shenandoah Valley, Winchester today serves as the area’s medical, industrial, commercial and agricultural hub.

The area of Winchester and Frederick County was settled by Pennsylvania Quakers in the 1730s on lands that were once Shawnee Indian camping grounds. In the 18th and 19th centuries The Great Valley Road, which is now known as Route 11, served as a migration trail.

Some famous names stand out among those who have walked Winchester’s streets. The city was the home of General Stonewall Jackson’s Headquarters during the winter of 1861-62. From 1748 to 1758, George Washington’s had an office in Winchester. The city was also home to singing legend Patsy Cline.

There are countless opportunities for adults traveling without children to have fun in Winchester and the surrounding area. Among my favorite discoveries…

Old Town Winchester
Winchester VAWith over 35 restaurants and 60 retail shops, Old Town Winchester is the cultural heart of the city and surrounding area. Along the walkable streets and inside the architectural charms of this historic district, discover breweries, nightlife, street performers, more than 80 days of events (including beer and wine festivals), and more. Historic, quaint and inviting, the neighborhood has a vibe that says, “Come, hang out.”

I strolled through one evening between my hotel and 50/50 Taphouse, a casual restaurant where the menu offers 50 different versions of burgers (plus, if that’s not enough, you can order a custom creation) plus 50 different craft brews on tap.

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Horseback Riding
Winchester VASeveral horseback riding options and opportunities dot the foothills just outside of Winchester, including Magic Mountain Farm where hour-long expert-guided rides weave from the stables up and down scenic trails. Whatever your riding ability and skill-level, the pros at Magic Mountain Farm will pair you with an appropriate, gentle animal. The Farm’s horses are well-trained and clearly loved. Though familiar with the trails, these horses respond well to riders’ cues. In addition to getting some exercise in fresh air, horseback riding is a memorable way to enjoy Shenandoah Valley’s spectacular views!

Museum of the Shenandoah Valley
The Museum presents the art, history, and culture of the Valley. The 50,000-square-foot main building houses a permanent collection of over 11,000 pieces including fine and decorative arts, miniature houses and furniture (think elaborate dollhouses), baskets and ceramics, paintings, silver, textiles, and more. A special exhibition, Under the Appalachian Sky: The Paintings of Barry Vance (a personal favorite, which will be on display through June 3, 2018) depicts life in the Appalachian Mountains of Virginia and West Virginia in soft colors. Beyond the Museum, the surrounding 214 acre landscape is the largest green space in Winchester and includes The Glen Burnie House (circa 1794) and its seven-acre gardens.

Winchester VA

Orchards & Farm Markets
Rumor is that George Washington planted many of the first apple trees in the area; commercial production began after the Civil War. These days, the National Fruit Product Company, which produces the White House apple products sold nationwide, is based in Winchester.

Winchester VAWinchester VA

Many area farmers invite you to pick your own apples (in season), though you can also buy baskets and bushels of fruit alongside pies, jams, cider, doughnuts and other treats. If you drive to the area, you’ll be glad for the chance to easily toting home all the temptations and goodies that beckon from stands along the roadsides. Among them…

  • Marker Miller Orchards & Farm Market offers you-pick opportunities, lots of homemade preserves, and a bakery.
  • Richard’s Fruit Market is the oldest “country classic” open air farm market in the county; in addition to fruit you can stock up on beef, vegetables, fresh baked goods, wine and flowers.
  • Virginia Farm Market is an open-air market that specializes in produce and baked goods.
  • Established in 2016, The Homestead Farm at Fruit Hill Orchard sells organic and non-GMO produce, homemade baked goods, jams and jellies, raw honey, plus household items and gifts. Though the market is new, the farm has been in the family for five generations. You-pick options are available from May through November, with seasonal options ranging from blackberries to apples, raspberries to peaches. Don’t miss Winchester Cider Works, located next door: The flagship Malice hard cider is blended with five different apple varietals from local Shenandoah Valley orchards and it’s serious yum.

Winchester VAWinchester VA

Even more reasons to visit…
Where To Stay…

The George Washington Grand Hotel

More Information…

Winchester VAWinchester-Frederick County CVB
1400 S. Pleasant Valley Road
Winchester, VA 22601

Visit Virginia

– Photo Credits: City aerial, Old Town Winchester, horseback riding and beer tap images courtesy Winchester-Frederick County CVB; remainder © HSP Media LLC. Click on individual images for details.

Featured products, services and/or travel arrangements may have been complimentary in part or in full; this affords the research opportunity but does not sway opinion. Winchester hosted #MATPRA2017.

Hope S. PhilbrickHope S. Philbrick is founder and editor-in-chief of Getaways for Grownups. She became a freelance writer and editor because she believes that work and fun should not be mutually exclusive. Her work has appeared in dozens of publications nationwide. When not writing, she can usually be found on the road or savoring something tasty.

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