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Winchester, Virginia, is a charming little city situated in the hills of the Shenandoah Valley. It has a very rich history, which you can learn at one of the museums in the city. It is also home to a lot of historic structures and landmarks. Nature-lovers would also appreciate the city with its hills and countryside that surrounds it, so you can hike, swim in lakes, harvest at farms and orchards, and indulge in many other activities. Get to learn more about the best things to do in Winchester, Virginia, and bring your family and friends to visit the city on your next vacation.
You will never run out of things to see as you wander through the Old Town Winchester. Also known as the Loudoun Street Pedestrian Mall, this brick-lined street is famous for its restaurants, shops, a Civil War Museum, and other historic buildings. Theres also a splash pad for kids to have fun during summer. It also becomes a venue for different events such as a summer Farmers Market, and Apple Blossom Festival.
Old Town Winchester
Museum of the Shenandoah Valley
Address: 901 Amherst St, Winchester, VA 22601, United States
Opening hours: Tue – Sun: 10am – 5pm
Robert Burns Supper With Winchester Pipes And Drums
Burns Night is considered to be Scotlands other national day, alongside St Andrews Day in November. Celebrated on the same date each year, the night gives a nod to the life and work of the Scottish poet, Robert Burns. Burns Night is a staple celebration in the Scots calendar, and for good reason. The annual … Read more
More Historic Sites In Downtown Winchester
George Washington developed his reputation and skill as a commander while living and working in the Winchester area. Visit George Washingtons Office Museum to learn about his time in the area, Here he planned and oversaw the construction of Fort Loudoun.
Winchester changed hands 72 times during the Civil War, more than any other U.S. town. Today, that history is preserved and interpreted at several area sites. The Shenandoah Valley Civil War Museum is located on the pedestrian mall. It occupies a courthouse that was used as a hospital and prison during the Civil War. Nearby, Stonewall Jacksons Headquarters is preserved as a museum.
Explore musical history at the Patsy Cline Historic House, half a mile from the mall. The country music legend, Patsy Cline, lived in the modest Winchester home from the age of 16 to 21.
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Wander Around The Museum Of The Shenandoah Valley And The Glen Burnie Historic House & Gardens
You could spend an entire day trip to Winchester just at this museum! There are four significant galleries, rotating exhibitions, a café, and a museum store at the Museum of the Shenandoah Valley.
Their 7 acres of gardens are exquisite. As you wander the grounds, youll see how they incorporated distinct gardens dedicated to roses, statues, vegetables, Chinese-style, and perennials throughout.
They also have various musical performances, youth workshops, and other sets of exciting events for kids throughout the year. You can find the calendar of events on their website.
The Glen Burnie House is included in the regional cultural center. The oldest parts of the historic house were built by Robert, James Woods son, in the late 1790s, and his descendants inhabited the residence all the way up to 1992. Experience the house and beautiful gardens to learn stories about those who lived here.
Have A Blast At The Apple Blossom Festival
My first memories of Winchester were actually its association with the Apple Blossom Festival every May in Virginia. I still have yet to go but it is on my ever-growing Virginia list of events to attend.
The Apple Blossom Festival is a six-day festival held in the Old Town of Winchester and is definitely one of the best things to do in Winchester if youre there when it is taking place.
The festival started in 1924 and is one of the oldest celebrations in the state. It did not take place from 1942-1945 as a result of WW2 but has been a Virginia favorite ever since . There are concerts, dancing, walks, carnivals, and much more.
Even former US President Lyndon B. Johnson attended the festival. It lures in around 250,000 people each year and the main highlights of the Apple Blossom Festival are the Old Town Wine & Fine Arts Festival and the Apple Blossom Carnival.
It is such a large part of the citys culture and history that the citizens all chip in to hold an annual clean up before it starts to make sure everything looks great for the visiting guests.
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George Washington’s Office Museum Winchester Virginia
George Washingtons Office is a museum housed within a log cabin and holds many of President George Washingtons personal items as well as period artifacts and other historical features. The president used the log cabin as his military office from 1755 to 1756. There are a number of artifacts displayed in the office, including a cannon that was left behind in Alexandria by General Edward Braddock. There are also several personal items from George Washington, exhibited alongside a model of Winchester from 1755, which includes Fort Loudoun. The museum is open seasonally for touring and features a gift shop and occasionally hosts special events and exhibitions.
32 W. Cork Street, Winchester, VA 22601, Phone: 540-662-4412
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Patsy Cline Historic House Winchester Virginia
The Patsy Cline House is the historic home of Virginia Patterson Hensley, who lived in the home from 1948 to 1953. She later became known as Patsy Cline and had a successful career as a country music star, and the Greek revival home is open as a museum home dedicated to Clines life and career. The home was her residence during many of the years she was pursuing her dream to be a musician. The home is only open seasonally for touring, and the tour includes the garden. There is an on-site gift shop where visitors can purchase items related to the home, Patsy Cline, and country music in general.
608 S. Kent Street, Winchester, VA 22601, Phone: 540-662-5555
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For A Taste Of What To Expect
Explore the medieval streets of Winchester and admire the history of Winchester Cathedral, Wolvesey Castle and Winchester City Mill before strolling along the River Itchen to The Hospital of St Cross. Why not end your day with an evening of comedy, theatre, ballet or opera at one of Winchesters entertainment venues in the cultural quarter of the city.
Firmly established as a foodie destination, make sure you visit the largest Farmers Market in the UK or indulge in a pub lunch and sit beside a roaring log fire.
Youll find something to suit you, whether youre a lover of the great outdoors looking for an active holiday, or simply want to spend a romantic weekend exploring Winchesters history and heritage.
Why not extend your stay so you can make the most of the beautiful countryside and idyllic villages surrounding Winchester?
Hire a bike or simply take a stroll through the South Downs National Park, taking in some of the most breathtaking views across Hampshire.
Youll find plenty of attractions outside of the city to keep the whole family amused. Enjoy a free day out at Fort Nelson a unique Victorian Fort and home to the Royal Armouries national collection of artillery the Big Guns. For a nostalgic day out take a ride on the restored steam trains at the Mid Hants Railway, stopping off to explore the beautiful market town of Alresford. Or step into Africa and meet some of the most fascinating animals on earth at .
Discover The State Arboretum Of Virginia Blandy Experimental Farm
Take to the Virginia Native Plant Trail and paths throughout the 172-acre arboretum, where you will be at home with the 5,000 woody trees and shrubs from around the world.
Here you can view one-third of all the worlds species of pines, a grove of 300 ginkgo trees, a Lebanon allee, and explore the herb garden.
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Cedar Creek & Belle Grove National Historical Park Winchester Va
Cedar Creek and Belle Grove National Historical Park was created in order to protect and preserve several historically and culturally significant locations throughout the Shenandoah Valley region and it is the perfect stop to put on your list for any history buffs in your family. The most significant site in the historical park is the location of the American Civil War Battle of Cedar Creek. The Belle Grove Plantation is also a significant site and is open to the public for touring. The park rangers offer a number of programs for visitors, which include historical and cultural programming related to the Shenandoah Valley as well as interesting looks at the Battle of Cedar Creek and the deep impact that the Civil War had on the region.
Middletown, VA, Phone: 540-869-3051
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Enjoy Small Talks At Oak Stone Craft Pizza And Bar
Bring your family and friends over for a great dining experience at Oak Stone Craft Pizza and Bar. It is an independent American restaurant that specializes in pizza. Here they cook in wood-fired ovens made of homemade dough and topped with the best ingredients. They also serve side dishes and salads, which are perfect to be paired with their fine collection of beers and wines.
Oak stone Craft Pizza and Bar
Address: 1000 Valley Ave, Winchester, VA 22601, United States
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Patsy Cline Historic House
Explore musical history at the Patsy Cline Historic House, half a mile from the mall. The country music legend, Patsy Cline, lived in the modest Winchester home from the age of 16 until she was 21.
Patsy Cline was one of the most influential singers of the 20th-century, and she is one who was able to successfully crossover from country music into pop music.
Explore The George Washington Office Museum
When looking for things to do around Winchester, a stop at the George Washington Office Museum should be near the top of your list.
Visit the military office that George Washington used for 16 months from 1755 to 1756 as he planned and constructed Fort Loudoun. As you tour the museum, you will learn about his time in Winchester and see some personal artifacts of Washingtons, such as some of his surveying equipment and hair. Outside the museum, there is a Fort Loudoun cannon.
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Where To Stay In Winchester
- In the Old Town Theres a reason why everyone loves the George Washington Hotel . Only a block away from the heart of historic downtown Winchester on East Piccadilly Street, the restored historic hotel is found in a Georgian Revival brick building. Now a Wyndham Grand Hotel property featuring amenities like an indoor pool, a spa tub, and a full-service spa on-site, its a phenomenal place to base yourself when you visit.
- Apartment stay If youre looking for an apartment stay in downtown Winchester, this beautiful Airbnb is within walking distance of the Old Town. Originally known as the Seymour House, built in 1776, today, its a fully renovated space with everything youd need for a romantic getaway.
- Close to Shenandoah University Attached to a shopping center, the Hampton Inn Winchester is great if youre visiting Shenandoah University. Within walking distance to the college, the standard Hilton-brand hotel features a couple of choice amenities, like an outdoor pool during the summer season and an on-site fitness center.
- Luxury stay Although its a little outside the city, LAuberge Provencale is worth the splurge. The picture-perfect bed and breakfast is a 20-minute drive from the Old Town of Winchester and home to an outdoor seasonal pool with a beautiful terrace to enjoy your complimentary breakfast, an on-site spa, and a restaurant with its own bar and lounge.
Walk Or Ride A Bike At Third Winchester Battlefield Park
Editor’s Note: There’s no photo available at the time of writing
Featuring 5 miles of walking and biking trail, Third Winchester Battlefield is open for everyone all year round. One can embark on self-guided tours on this path that comes with signage and amazing views. The area also witnessed one of the biggest wars in the United States, where millions fought and around 8,600 casualties were recorded. After your walking or biking adventure, make sure to stop by their new visitor center and check out the Civil War-era displays and videos.
Third Winchester Battlefield Park
Address: 541 Redbud Rd, Winchester, VA 22603, United States
Opening hours: 5am – 9pm
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Swoon Over Antique Cars
If I had a choice and no budget necessary, my ideal drive would be a 1940s truck. Id want it to be that gorgeous shade of rusty brown but put a rust deterrent on it and give it a clear coat. Ahh, a gal can dream.
If you love antique, restored vehicles, youll definitely want to head to Jacks Auto Sales. A little bit quirky but a whole lot of fun, you can browse his latest acquisitions both indoor and out.
Abrams Creek Wetland Preserves
Abrams creek wetland preserve is a place famous for offering a natural vacation destination to people. Ideal for picnicking, cycling, jogging, walking and even idly sitting, the place is just so rich in its natural content, it will take your heart away.
The place is surrounded by a wide range of wildlife species, providing habitat to animals as well as the birds in this same place. It also has a great variety of plants, which makes the creek a suitable place of someone interested in flora and fauna.
You can also take a guided tour to the creek to get a better idea about the variety of flora and fauna in the area or simply decide to keep it all to yourself without any professional guide.
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Handley Library And Downtown Architecture
A block from the pedestrian mall is one of the finest Beaux-Arts buildings in the area, the Handley Regional Library. The beautiful exterior was designed to suggest an open book. The rotunda forms the spine and two wings are the books covers. Climb the pretty curving stairwell inside for a closer look at the stained-glass rotunda.
Visit The Patsy Cline Historic House
Country music legend Patsy Cline was born in Winchester, Virginia, on September 8, 1932. She became one of country musics most popular singers and one of the first to successfully cross over from Country to Pop. Tragically, she died at the age of 30 in a plane crash on March 5, 1963, returning from a concert tour in Kansas City, Kansas.
However, before the world knew her as Patsy Cline, Virginia Patterson Hensley lived just outside the Old Town area of Winchester in a humble home from age 16 through 21 and returned to the house many times after that. At the Patsy Cline House, visit her teenage home and learn about the woman she was before she became a legend. Find opening dates and tour hours on the towns website.
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Learn And Shop With The Artisans In Berryville Va
Many artisans make their home and sell their wares in the small town of Berryville, in neighboring Clark County. Begin at the Barns of Rose Hill Cultural Arts Center to see current exhibits and learn about the artisans in town. The Barns also host special events and live entertainment. Next, wander through the downtown area, visiting shops and speaking with artisans about their creations.