Winchester (Virginia)

Travel Guide North America USA Southern United States Virginia Winchester



Nestled between the Appalachian and Blue Ridge Mountains, with-in the beautiful Shenandoah Valley, Winchester-Frederick County is home to the City of Winchester and the Towns of Stephens City, Middletown, and Gore.

Area History

Winchester and Frederick County was once Shawnee Indian camping grounds to which Pennsylvania Quakers came to settle in 1732. The town was named Frederick Town after Frederick, father of George III of England. In 1752 the name was changed to Winchester in honor of the ancient English capital.

In the mid-1700’s, Frederick County became the military and political training ground for George Washington, who came here at the age of sixteen to survey the lands of Thomas, the Sixth lord Fairfax. Washington built Fort Loudoun during the French and Indian War and, at twenty-six, was elected to his first public office as the county’s representative to the House of Burgesses.

During the Revolutionary War, Daniel Morgan’s Rifleman from Frederick County were among the first who came to Washington’s aid against the British.

Winchester was a strategic prize of great importance during the Civil War. The area became the scene of six battles during the Civil War, and the city itself changed flags around seventy times during the four year conflict. General Thomas “Stonewall” Jackson demonstrated his military leadership in the Valley Campaign.

Winchester has long been known as the “Apple Capital” surrounded as it is by vast orchards and constituting one of the largest apple export markets of the nation and the largest producing area in Virginia. Winchester is known for its annual spring event, the Shenandoah Apple Blossom Festival, which draws crowds in excess of 250,000 each year.




Stephens City



Sights and Activities

John Handley High School is an endowed public high school located in the city of Winchester, Virginia. It was founded by a grant from Judge John Handley, hence the school mascot, the Judges. Construction on Handley High School started in 1922, and continues to the present day. Recently, the school completed the final phase of its multimillion-dollar renovation with the addition of an 8-lane track and a turf football field. The school is planning renovations to its tennis courts in the upcoming years, due in part to the girls' three-peat state champions. In 1998, Handley was placed on the list of the National Register of Historic Places.
Handley Library is a historic library building located at 100 West Piccadilly Street in Winchester, Virginia, United States. Completed in 1913, construction of the Beaux-Arts style building was funded by a wealthy Pennsylvania businessman. The building serves as the main branch for Winchester's library system. It was listed on the National Register of Historic Places (NRHP) and Virginia Landmarks Register (VLR) in 1969.
Stonewall Jacksons Headquarters
Sheridan's Headquarters



Events and Festivals


  • New Year’s Eve - The US celebrates the outgoing of the old year and incoming of the New Year quite dramatically. Every state boasts its own parties to ring in the New Year, but none is more extravagant than New York’s Time Square, which sees people overflowing into the neighboring restaurants, bars, parks, beaches, and neighborhoods.
  • Martin Luther King Jr. Day (officially Birthday of Martin Luther King, Jr. and sometimes referred to as MLK Day) is an American federal holiday marking the birthday of Martin Luther King Jr. It is observed on the third Monday of January each year, which is around King's birthday, January 15. The holiday is similar to holidays set under the Uniform Monday Holiday Act. The earliest Monday for this holiday is January 15 and the latest is January 21. King was the chief spokesperson for nonviolent activism in the Civil Rights Movement, which successfully protested racial discrimination in federal and state law.
  • St Patrick’s Day - March 17 celebrates the US’s large Irish population. Many cities around the country boast boisterous parades and Irish-themed parties, especially New York and Chicago, where the river is dyed green. Be wary of the drunkenness that dominates as this is definitely a party-day.
  • Memorial Day - Memorial Day is an important holiday throughout the United States, but not for crazy festivities. Parades commemorating wartime heroes are often held and the day is also the ‘unofficial’ start of summer. Most visitors follow the crowds to parks and beaches, which are capped off with informal BBQs.
  • Independence Day - Also known as the Fourth of July, Independence Day celebrates the US’s break from the British during the 18th century. Barbecues, street parties, beach trips, and weekend getaways are commonplace to appreciate freedom.
  • Labor Day is a public holiday celebrated on the first Monday in September. It honors the American labor movement and the contributions that workers have made to the strength, prosperity, laws, and well-being of the country. It is the Monday of the long weekend known as Labor Day Weekend. It is recognized as a federal holiday. Beginning in the late 19th century, as the trade union and labor movements grew, trade unionists proposed that a day be set aside to celebrate labor.
  • Halloween - Halloween is a fun holiday on October 31 for all generations to dress up in costumes and relive their youth. Children walk around the neighborhood trick-or-treating for candy, while adults attend parties. Other seasonal events include haunted houses, pumpkin farms and carving, and corn mazes.
  • Thanksgiving - On the fourth Thursday in November, Thanksgiving is held in almost every home in the US. Tourists will have a hard time finding anything to do as the country essentially shuts down in observation. A typical Thanksgiving meal consists of turkey, stuffing, mashed potatoes and pumpkin pie commemorating the original Pilgrim’s feast at Plymouth Rock.
  • Christmas - On December 25, Christians celebrate Christmas as the pinnacle of their calendar by attending church and opening gifts from Santa Claus. Almost everything shuts down to promote family togetherness. The northern regions hope to experience a “white Christmas,” with trees and festive lights blanketed by snow.


  • Super Bowl Sunday - the world’s most watched sporting event and one of the highest grossing TV days of the year, Superbowl Sunday is a spectacular extravaganza. Held the first Sunday in February, the Superbowl is the final playoff game between the NFL’s top two teams. The venue rotates every year around America, yet the local parties seem to remain. Pubs, bars and restaurants are great places to enjoy the Superbowl or locals throw their own parties with different variations of betting.
  • The World Series is the annual championship series of Major League Baseball (MLB) in North America, contested since 1903 between the American League (AL) champion team and the National League (NL) champion team. The winner of the World Series championship is determined through a best-of-seven playoff, and the winning team is awarded the Commissioner's Trophy. As the series is played during the fall season in North America, it is sometimes referred to as the Fall Classic.

Other Events and Festivals

  • Fourth of July Celebration at Sherando Park - Frederick County’s Independence Day celebration is held at Sherando Park and includes a day of swimming at the outdoor pool, live music, and plenty of room to spread out your blankets to enjoy the fireworks show. July 4.
  • Frederick County Fair - Livestock, petting zoo, pageants, demolition derby, tractor pulls, monster trucks, educational exhibits, a carnival, live music, and traditional fair food are just some of the reasons to come to the fair! Last week of July.
  • Hop Blossom Craft Beer Festival - Beer festival featuring 40+ breweries, a homebrew competition, and live music in Old Town Winchester. Mid-June.
  • Middletown's 4th of July Celebration and Parade - The small town of Middletown hosts this all-day event featuring a softball tournament, food and craft vendors, inflatables for the kids, a parade down Main Street, and live music in the town park before an awesome fireworks show. July 4.
  • Newtown Heritage Festival - A free family festival that celebrates the town of Stephens City’s heritage and includes wagon rides, a parade, a craft show, and fireworks. May – Memorial Day Weekend.
  • Of Ale & History Beer Festival - Sample an array of beers from the New and Old World. Music provided by live bands, food, and tours of the historic home, all in a scenic outdoor setting. May – Mother’s Day Weekend.
  • Rock'n Independence Eve - This annual All-American celebration includes live music, street performers, kids’ activities, and a spectacular fireworks show in Old Town Winchester. July 3.
  • Shenandoah Apple Blossom Festival - An annual family-friendly festival which has been around for over 90 years includes more than 30 events: marching band competitions, dances, a Firefighter’s Parade, a Grand Feature Parade, a 10K race, a carnival, celebrities, Weekend in the Park, and much more! Late April – Early May.
  • Shenandoah Apple Harvest Festival - Held annually for over 40 years, this festival celebrates apples! Arts and crafts show, live music, apple pie eating contest, apple butter making, bingo, inflatables, face painting, and craft beer and hard cider tastings. Third Weekend in September.
  • St. Paddy's Celtic Fest - This free festival celebrates the community’s Irish and Scottish heritage with Celtic inspired music, dance, and the City of Winchester Pipes and Drums performing in Old Town businesses and along the Loudoun Street Mall. Second weekend in March.
  • Old Town Parade - Start the holiday season in Old Town! Join us on November 30 at 7pm for the annual holiday parade and tree lighting.
  • First Night Winchester




The summers are warm and humid, the winters are very cold, and it is partly cloudy year round. Over the course of the year, the temperature typically varies from 26 °F to 87 °F and is rarely below 12 °F or above 95 °F.

Based on the tourism score, the best times of year to visit Winchester for warm-weather activities are from early June to mid July and from late July to late September.



Getting There

From Washington, DC Take I-66 West to I-81 North, Exit 313. Turn right off the exit, keep right onto Millwood Avenue. Turn right onto Pleasant Valley Road. Visitors Center is on the right.

From Dulles Airport Head east on Saarinen Circle. Continue onto Dulles Access Road. Take exit 9A toward Washington/Virginia 28/Virginia 267/U.S. 50/U.S. 7/Sterling/Centreville/Interstate 495. Keep right at the fork and merge onto VA-267 W. Take exit 1A on the left to merge onto US-15 S/VA-7 W toward Leesburg/Warrenton. Continue onto VA-7 W. Route 7 becomes Berryville Avenue in Winchester. Turn left onto Pleasant Valley Road. Visitors Center is approximately 1 mile on the left past Jim Barnett Park.

From the North Take I-81 South to Exit 313. Turn right off the exit, keep right onto Millwood Avenue. Turn right onto Pleasant Valley Road. Visitors Center is on the right.

From the South Take I-81 North to Exit 313. Turn right off the exit, keep right onto Millwood Avenue. Turn right onto Pleasant Valley Road. Visitors Center is on the right.

From the East Take Route 50 West toward Winchester. Keep right as Route 50 becomes Millwood Avenue. Turn right onto Pleasant Valley Road. Visitors Center is on the right. Or, take Route 7 West toward Winchester. 7 West becomes Berryville Avenue. Turn left onto Pleasant Valley Road. Visitors Center is approximately 1 mile on the left past Jim Barnett Park.

From the West Take Route 50 East toward Winchester. Route 50 becomes Amherst Street. Keep right onto Boscawen Street. Turn right onto Braddock Street. Turn left onto Millwood Avenue. Turn left onto Pleasant Valley Road. Visitors Center is on the right.

By Plane

Winchester Regional Airport, a General Aviation airport, serves as the front door to the community. Dating back to the 1931 Apple Blossom Festival when an airshow took place at Byrd Field to what is now Winchester Regional Airport a few miles south, the airport continues to serve many purposes.

The benefits include but aren’t limited to business aviation, law enforcement, agricultural, lifesaving services such as emergency medical services, air ambulance operations and organ transports, freight and package delivery, as well as recreational use.

There are 41.18 miles from Washington Dulles International Airport (IAD) to Winchester in northwest direction and 51 miles (82.08 kilometers) by car, following the VA 7 or VA 50 route. IAD Airport and Winchester are 1 hour 2 mins far apart, if you drive non-stop.

There are 64.57 miles from Winchester to Ronald Reagan Washington National Airport (DCA) in southeast direction and 77 miles (123.92 kilometers) by car, following the VA 7 route. Winchester and DCA Airport are 1 hour 29 mins far apart, if you drive non-stop.

There are 80.06 miles from Baltimore–Washington International Airport (BWI) to Winchester in west direction and 98 miles (157.72 kilometers) by car, following the I-70 route. BWI Airport and Winchester are 1 hour 45 mins far apart, if you drive non-stop.

By Train

There is 1 Amtrak train station within 30 miles of the Winchester city center.

By Car

Multiple highways to get to Winchester. US-50, US-7, US-522, I-81, Route-11

You are invited to “ride the sky” along Skyline Drive, one of America’s favorite mountain drives. Just 17 miles south of Winchester in Front Royal, the historic 105-mile Skyline Drive, a National Scenic Byway, traverses Shenandoah National Park, a beautiful, historic national treasure.

The mountain top highway winds its way north-south through Shenandoah’s nearly 200,000 acres along the spine of Virginia’s Blue Ridge Mountains.

Shenandoah National Park varies in width from less than one mile to about thirteen miles, so that views from peaks and overlooks will captivate and delight. There are 75 scenic overlooks that offer stunning views of the Shenandoah Valley to the west or the rolling Piedmont to the east. While you are gazing out at the views, keep a close eye on the road too, as deer, black bear, wild turkey, and a host of other woodland animals call Shenandoah home and regularly cross Skyline Drive in their daily travels.

Roadside wildflowers put on a show all year long. In early spring, you can see trillium peeking through the grass. June’s display of azaleas is spectacular, and cardinal flower, black-eyed susans, and goldenrod keep the color coming right into fall.

As you travel along Skyline Drive you will notice mileposts on the west side (right side if you are traveling south) of the road. These posts help you find your way through the park and help you locate areas of interest. The mileposts begin with 0.0 at Front Royal and continue to 105 at the southern end of the park. The speed limit is 35 mph. It takes about three hours to travel the entire length of the park on a clear day. Clearance for Marys Rock Tunnel (just south of Thornton Gap entrance from Route 211) is 12’8”.

Skyline Drive is your gateway to Virginia adventure.
Skyline Drive is closed only in snow or ice, and at night during deer-hunting season. Inclement weather may necessitate closure of Skyline Drive at any time






Keep Connected


There is a very small internet bar/cafe culture in the USA. Even then most of the internet bars/cafes tend be located in major urban centers. Accessible WiFi networks, however, are common. The most generally useful WiFi spots are in coffee shops, fast-food chains, and bookshops, but also restaurants and hotels more and more have a network to connect on. Some of them might require you to buy something and you might need a password too, especially in hotels.


See also International Telephone Calls

The general emergency phone number is 911. The USA has a great landline phone system that is easy to use. The country code for the U.S. is +1. The rest of the telephone number consists of 10 digits: a 3-digit area code, and a 7-digit number. Any small grocery store or pharmacy has pre paid domestic or international phone cards. These phone cards are very cheap and offer good rates. The once ubiquitous pay phone is now much harder to find. Likely locations include in or near stores and restaurants, and near bus stops. The cellphone network in the states is slowly getting better but is still not as good when compared to other western countries. Cell phones tend to operate using different frequencies (850 MHz and 1900 MHz) from those used elsewhere in the world (2100 MHz). This used to prevent most foreign phones from working in America. Phones must be tri- or quad-band to work in the U.S. Fortunately, technology has meant that most phones should now be able to pick up one of the U.S. networks. Prepaid phones and top-up cards can be purchased at mobile phone boutiques and at many discount, electronics, office supply and convenience stores. A very basic handset with some credit can be had for under $40.


The US Postal Service is a very good and well priced mail system. There are post offices in every small and large town for sending packages internationally or domestically. Although some might keep longer hours, most are open at least between 9:00am and 5:00pm. If wanting to send a letter or postcard it is best just to leave it in a blue mail box with the proper postage. First-class international airmail postcards and letters (up 28.5 grams) cost $1.10. There are also private postal services like FedEx, UPS, TNT and DHL, which might be better value sometimes and are generally very quick and reliable too.


Quick Facts


9.21 sq mi (23.86 km2)
Population: Winchester
Frederick County

Winchester (Virginia) Travel Helpers

This is version 9. Last edited at 11:40 on Nov 4, 19 by Utrecht. 1 article links to this page.

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