Best Things to Do in Winchester, VA (A Traveler’s Guide to Fun)

Officially becoming a city in 1752, Winchester is an exciting place to visit.

This is the land George Washington surveyed in his youth.

This is land that has deep ties with the history of not only Virginia but the formation of America.

This is the land that treats you to the majestic beauty of the Shenandoah Valley, and all the adventure it holds.

But with so many wonderful things to do, see, and experience here, we want to make sure you don’t miss anything on your visit.

With our decades of new-home building expertise, DRB Homes not only knows what homeowners want but also what they want to live near. And we want to share that knowledge with you!

Here is a small version of some of the best things to do in Winchester, VA. Consider it your traveler’s guide to fun!

DRB Homes in Winchester

Of course, the only thing better than visiting Winchester is living here: So, we had to mention at least one DRB Homes property! Welcome to the townhomes at Lofts at Creekside.

Our exclusive new townhome designs give you super spacious kitchens with tons of room for entertaining and creating a special dining space. Large owner’s bedrooms feature walk-in closets, attached baths, and two optional ceiling treatments. Add in a lower-level rec. room and an optional 4^th-floor loft and deck area, and you have one fantastic home.

And being close to everything that Winchester has to offer, makes Lofts at Creekside even more appealing. Now, let's explore Winchester!

Historical and Cultural Attractions

Like we already mentioned, Winchester is older than our country. As such, of course, it’s gained a rich history and developed a dynamic culture. Here are just three unique places you can visit:

Old Town Winchester

Old Town Winchester brings the past and the future together in one magical location. Historic architecture greets you at every turn. Explore the old-town charm of the Walking Mall: a pedestrian-friendly area surrounded by delicious dining and boutique shops. There’s even a Splash Pad at one end to cool off in during the summer. Old Town Winchester is where you come for museums, live music, and community festivals and celebrations—all year long!

Stonewall Jackson’s Headquarters

This Virginia and National Historic Landmark was used by the Confederate General during the winter of 1861–1862. Now a museum, Stonewall Jackson’s Headquarters has the largest collection of memorabilia from the General’s personal artifacts. Plus, his office has been thoroughly preserved so it’s almost exactly the same as when it was used. Plus, there’s a gift shop!

George Washington’s Office Museum

Used later in his life than when he was surveying Winchester, George Washington relied on this office as his homebase as he oversaw the building of Fort Loudoun (1755–1756) during the French & Indian War. You can, however, see his survey equipment here at the museum, along with some of our first president’s personal effects and a scale model of the town as it looked in 1755!

Outdoor Adventures & Scenic Beauty

You can’t come to Winchester and not explore the outdoors. From the beauty of the Shenandoah Valley, to the many parks and lakes, to the mountains on either side, all of it calls out to you. Here are a few of our favorite outdoor adventures and places of immense natural beauty:

Winchester Green Circle Trail

The Winchester Green Circle Trail is a scenic way to see Winchester. A work in progress, this trail circles the city connected bicyclists and pedestrians to many points of interest, including the Glen Burnie Historic House and Gardens, Jim Barnett Park, Shenandoah University, Old Town Winchester, and the Abrams Wetland Preserve. Spur trails also go into the center of the city, putting even more amazing options just a bike ride or walk away.

Shenandoah National Park

Just a short ride from Winchester is the glorious Shenandoah National Park. Here, over 200,000 acres of protected lands await you. Waterfalls, vistas, wildflowers, wild life, forests, and campgrounds surround you. Over 500 miles of trails take you in every direction. Birdsong and the wind through the trees compose the soundtrack. The only constant is: You’ll always be surrounded by natural beauty and enjoying one of the most pristine locations in Virginia.

State Arboretum of Virginia

Walking through the State Arboretum of Virginia is like walking through another land. Labelled tree and shrub collections date back almost 100 years and are sampled from all over the world. In all, 172 acres of remarkable wooded wonderland stands tall, including a boxwood garden, ginkgo grove, and the largest conifer collection in the Southeast. And even better, the State Arboretum of Virginia welcome families of all shapes and sizes, including kids and dogs!

Cedar Creek and Belle Grove National Historical Park

The Battle of Cedar Creek was a decisive win for Union troops. It resulted in the capture of Confederate artillery, disrupted Confederate production lines, and helped re-elect Lincoln. Now, this battlefield has been preserved as a National Park. Tour the Cedar Creek Battlefield and Mount Carmel Cemetery, explore the park’s many historic buildings, walk on wooden trails in the footsteps of history, and visit Belle Grove Plantation where you’ll learn about the owners and enslaved workers. At the Cedar Creek and Belle Grove National Historical Park, you’ll learn all the many factors that built this area (and, our country) into what we know today.

Wineries & Breweries

Another of the wonderful things about the Shenandoah Valley is the way the land supports all the crops necessary to create a fine wine or flavorful brew. Here are three places we recommend you visit:

James Charles Winery & Vineyard

Established in 2000, James Charles Winery & Vineyard is a family-run vineyard that sits on 10 acres of perfect for growing just the right grape. Their merlot and zinfandel varietals let these wine masters create delicious and vibrant wines that will perfectly pair with any meal. And speaking of meals, when you visit, make sure to sample the selection of gourmet food in their tasting room. Reserve your tasting or tour today!

Escutcheon Brewing Co.

Escutcheon Brewing Co. has a simple philosophy: make great beer and support the community at the same time. Every one of their classic craft beers is made on site, packaged on site, and served on site—and all in a relaxed and friendly atmosphere. This is a brewery where you become part of the family as you toast to another delicious day. Find your new favorite beer at your new favorite brewery: Visit Escutcheon Brewing Co.

Winchester Ciderworks

In 2012, Stephen Schuurman realized he missed the drier ciders of his British homeland. This was the

seed that grew into Winchester Ciderworks. Blending black currants, ginger, elderberries, and more to their aged apple juice, Winchester Ciderworks produces sparkling ciders that aren’t as sweet as American ciders, but they are just as delightful. Tickle your palate with a high-quality, home-brewed cider and satisfy your cider thirst.

A Traveler’s Guide to the Best Things to Do in Winchester, VA

Winchester, VA, is a must-experience destination. With a unique blend of history, culture, outdoor fun, and great local wines and brews, every visit is an adventure. Our best bit of advice is to explore the city’s charm at your own pace. There’s so much to do here, you’ll want to visit again and again.

Or better yet, visit DRB Homes and find your new home in Winchester. Then, you can live the Shenandoah Dream day after day from the comfort and happiness of your own Winchester home!