Your Ultimate Guide to Winchester Virginia

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Winchester, Virginia is a small city – or large town – occupying the Shenandoah Valley. The city has become much more than just an homage to “Take Me Home, Country Roads.” Winchester is now a city full of global cuisine, delectable wineries, mountain views everywhere, and a vibrant and lively downtown.

About Winchester Virginia

Like most places in Virginia, Winchester is full of history. A number of pre Revolutionary War structures and houses line the town. Once a training ground for George Washington and the site of his Fort Loudoun during the French and Indian War.

The city then became a major battleground during the Civil War. During the four year war, Winchester would change sides about seventy times with six battles happening within the town limits.

Now the city has become known as the “Apple Capital of Virginia.” The area has become famous through literature and music for the Shenandoah Valley and Shenandoah River and lying along the famous Appalachian Mountains and the scenic stretch of Blue Ridge Mountains.

Winchester is only 70 miles from the nations capital – Washington, D.C. – making it a great place to get away from city life and enjoy some country living.

Stuff to Do in Winchester Virginia

You may be wondering what there is to do in the countryside of Virginia. The answer is everything. Winchester is the mix between country and city, the intersection of wine and beer, the blend of day hikes and night drinking. Winchester is whatever you want it to be.

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Virginia Spirits Trail

Northern Virginia is widely known for its spirits and Virginia even has its own spirits trail. The state has enjoyed their spirits for over 400 years and is the birthplace of American Spirits. Spirit enthusiasts often visit this area to get a taste of the American Spirit. This area is full of wineries, vineyards, cideries, and breweries and no trip is complete without a few drinks!

While Virginia has their spirits trail, there are other trails throughout the state that highlight the best spirits each region has to offer. The Shenandoah Spirits Trail is dedicated to showcasing and highlighting the best the valley has to offer.

Many of the wineries and vineyards are a drive outside of town but Valerie Hill Vineyard and Winery is located in adjacent Stephens City and only a 15 minute drive from downtown Winchester. The winery dates back to 1807 and has a rich history. Now set as a winery and vineyard, the manor house enjoys views of the valley and vineyard and the occasional spiritual entity.

The Shenandoah Spirits Trail boasts close to 50 establishments along the I-81 corridor. Other places within Winchester, Virginia on the Shenandoah Spirits Trail include:

Winchester Brew Works, Broken Window Brewing Company, and Escutcheon make up a large portion of the “beer mile” in downtown Winchester. This beer mile is a favorite among beer aficionados and friends looking for fun in the city.

Old Town Winchester

Old Town Winchester has become synonymous with downtown Winchester. This is the area of Winchester, Virginia that boasts a lively nightlife, food for all, and historic landmarks and buildings.

The most prominent aspect of Old Town Winchester is the pedestrian mall – the center of all things to do in Winchester. The walking mall takes up about two blocks on Loudoun Street but offers a wide variety of restaurants ranging in cuisine with Thai Winchester, Union Jack Pub and Restaurant, and El Centro Mexican Restaurant.

Old Town Winchester also boasts an array of brick and mortar shops that can be explored all day. From Virginia’s largest family owned shoe store – Wilkins Shoe Center – to a speciality oil and vinegar shop – Flavor Pourfection.

The walking mall and all of Old Town is home to 60 shops with apparel, adventure, pet, and book shops to cover all of your needs. The mall even has a spring and summer farmers market on the weekend for people to enjoy the valleys freshest picked fruits and vegetables.

Winchester Brew Works
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Winchester Virginia Nightlife

Old Town is also the epicenter of Winchester nightlife. Friday and Saturday nights are full of college students and locals walking through the streets of Old Town and dancing in the bars.

A typical night starts at Piccadilly’s Public House – a bar with indoor and outdoor seating, a grounded boat featuring bands, and some of the best fried pickle spears the state has to offer. Piccadilly’s is a favorite in town, with a lively and friendly crowd. The bar even has a projector on a neighboring businesses wall to watch sporting events while having a drink with friends.

A common stop after Piccadilly’s and only a short walk away is Brewbakers. Get here early because on Friday nights the bar turns up with a DJ and loads of dancing. The bartenders are efficient and friendly, the drinks are always pouring, and everyone comes home with an unforgettable story to tell. For special events, the bar opens up their back room for even more dancing and fun.

Those are the main two bars in town but if you are looking for a late weeknight drink, look to Milano’s. This bar is known for a wild time that you may or may not remember in the morning!

After a night of drinking in Old Town, stop by Snow White Grill – a historic piece of the city – or new in town, Benny Meleto’s.

Old Town Winchester Virginia farmers market
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Historic Winchester Virginia

As noted, Winchester, Virginia has a rich history and what better way to learn about the area than museums. There are plenty of museums all focusing on different aspects of the towns history and future throughout the city.

The Museum of the Shenandoah Valley is a highly visited attraction that tells the story of the valley, has rotating and new exhibitions constantly, gardens, and structures to explore.

Shenandoah Valley Discovery Museum is a children’s centric museum that focusing on teaching the next generation all about science. This Museum is perfect for family’s looking for a day inside and learning.

Within the walking mall is the Shenandoah Valley Civil War Museum. This museum covers the history of the valley and city during the Civil War.

Located around downtown and throughout the entire city are more historic houses focused on a historic figure like George Washington’s Office, Stonewall Jackson’s Headquarters, and the Fort Loudoun Historic Site.

In pop culture, Winchester is also home to the Patsy Cline Historic House.

The George Washington Hotel by Wyndham is full of its own history. The hotel offers visitors a grand experience while they are situated within the walls of the first Apple Blossom headquarters and a long and diverging history. The hotel is right in Old Town, has multiple restaurants and eateries, and even has an extravagant Roman style indoor pool.

Farms and Orchards

Winchester, Virginia is the apple capital of Virginia and they make sure you know it. The area is perfect for apple orchards and fruit farms to pick your own fruit and explore for the day.

A local favorite is Marker-Miller Orchards with their long lines of apple trees, pumpkins to pick, and delectable apple cider donuts.

The Homestead Farm and Fruit Hill Orchard offers fresh and seasonal fruits and vegetables to locals.

It is easy to find yourself roaming around the country roads around the valley and finding new farmers markets and orchards to shop at.

View of Shenandoah Valley from Old Rag in Shenandoah National Park
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Shenandoah National Park

Only a short drive outside of the city limits is Shenandoah National Park. Within the park is over 500 miles of hiking trails, about 100 miles of the famous Appalachian Trail, numerous waterfalls, and the scenic Skyline Drive.

This park can be explored for years and still only scratch the surface of the true wonders of the park.

While visiting you must go for a hike and drive Skyline Drive.

Skyline Drive is over 105 miles and offers scenic overlooks of the Shenandoah Valley and the Blue Ridge Mountains. The drive can take all day due to the slow speed limit and the constant stopping for valley views. Many people like to choose one section of the drive to explore for the day.

The park also offers magnificent hikes. The prominent hike in the park is Old Rag – a 10 mile roundtrip hike that offers unbeatable views of the Blue Ridge Mountains and Shenandoah Valley. If an all day, 10 mile hike doesn’t sound enticing to you, the park offers easier and shorter hikes like Hawksbill Gap – which is on the Appalachian Trail – or Dark Hallow Falls.

More Outdoors

Shenandoah National Park is a highlight of the area but there are plenty more parks and trails to explore around Winchester, Virginia.

George Washington and Jefferson National Forests are close by with their own range of trails and hikes to explore.

Bears Den Overlook is right outside the Winchester town limits and offers stunning views of the valley below.

Raven’s Rock is a popular hike on the Appalachian Trail that takes you into West Virginia. Be sure to bring extra water for this hike as it is along the rollercoaster portion of the trail.

Sky Meadow’s State Park is another popular park for a day outside.

Events in Winchester, Virginia

Winchester’s Apple Blossom Festival is the city’s call to fame. The Festival takes place through the entire month of April but the biggest and busiest portion of the festival is the first weekend in May.

The festival celebrates the apple blossoms in Virginia’s Apple Capital with partying, festivities, and lots of drinking.

The downtown is overtaken by the Midway – games and vendors – and surrounded by multiple parades. The university and schools shut down to let students wander the crowded downtown streets, hopping between bars and parties. There is a carnival with games and rides and then a fireworks show to really get the town going. Apple Blossom events cover the city with wine tastings, luncheons, and dancing.

The weekend is full of fun and blooming and a must for any spring time traveler.

Besides the Apple Blossom Festival, Winchester hosts their annual First Night Winchester in celebration of the New Year with fireworks and drinking.

View of Shenandoah Valley from Old Rag in Shenandoah National Park
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More to Do

Winchester is what the mid-Atlantic is all about. The city embodies the charm and chivalry of the South with the bustling vibes of the North. The city is an all time favorite of mine and a place I like to call home.

If you’re visiting Winchester be sure to visit some of my above favorite places and check out these bonus hits to get you through the stay.

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