Winchester Things to Do

  • Court House and Feltner Building
    Court House and Feltner Building
    by Ewingjr98
  • Court House Civil War Museum
    Court House Civil War Museum
    by Ewingjr98
  • George Washington Hotel
    George Washington Hotel
    by Ewingjr98

Most Recent Things to Do in Winchester

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    Shenandoah Valley Campaign Sesquicentennial

    by etfromnc Updated Jun 13, 2012

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    A Whirlwind in the Shenandoah: The formal celebration of the 150th Anniversary of Stonewall Jackson's Shenandoah Valley Campaign ended this past Sunday but the battlefields are still there and there will be continuing reenactments and other special events for the next three years, so y'all come.

    In the spring of 1862, amidst the breathtaking beauty of the Shenandoah Valley, Confederate Gen. Thomas J. "Stonewall" Jackson conducted one of the most brilliant and audacious campaigns in American military history. Jackson and his "foot cavalry" changed the course of the Civil War - and carved their names in history.

    Now, 150 years later, sites throughout the Valley are commemorating that campaign with a series of well over 35 exciting events - reenactments, living history programs, walking tours, driving tours, conferences, lectures, youth programs, memorial ceremonies, passport programs, and exhibits. Make your plans now to be part of those special programs - and to follow the dramatic story of the pivotal events of those war-torn days.

    A few notes about the first Battle of Winchester: Two days after being defeated by Gen. Jackson at nearby Front Royal, Union Gen. Nathaniel Banks having reached Winchester, attempted to reorganize his men and defend his base from the hills on the south side of the town. As Jackson's Army approached the Federal defenses from the south, Gen. Richard Ewell's Confederate division converged on Winchester from the southeast. On May 25, Ewell attacked Camp Hill, while the Louisiana Brigade of Jackson's Army outflanked and overran the Union position on Bowers Hill. As both lines gave way, panic spread through the Federal ranks as Banks' men raced through the streets of Winchester attempting to escape. Banks' shattered army withdrew north across the Potomac River. During the battle and the subsequent retreat, Banks lost more than 2,000 men along with most of his supplies, while Confederate casualties were only about 400.

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    "Crazy"

    by etfromnc Updated Jun 13, 2012

    Throughout the 1990s, I lived near Baltimore, Maryland. Since I was a pre-schooler, my parents had lived in Charlotte, North Carolina. When I lived in Maryland, I made relatively frequent trips between Maryland and North Carolina. Usually, I took a shortcut from Frederick, Maryland to Interstate-81 just south of Winchester but when I was not racing to get to my destination, I would often spend an hour or two in Winchester. I love that town and could very easily live there, IF I could afford it.
    It seemed that every time I went to Winchester, I "accidentally" found a great spot which I had previously been totally unaware was in the area. I am writing this tip because I have just learned some terrific news about one of those discoveries. It was a working class home in which Virginia Patterson Hensley lived from the age of 16 to 21. She left that home to marry contractor Gerald Cline and her name lasted much longer than did her four year marriage. We now know her as Patsy Cline, and, as we sometimes say, "The rest is history."
    There's little doubt that today's predominance of women country singers owe their success to the trail blazed by Patsy Cline in the male-dominated 1950s. As of last year fans—and aspiring singers—can visit the house where it all began.
    She did a lot of singing as a teen but her singing career really took off in 1957, about the time she split with Mr. Cline.
    Taking a long, slow, and often painful climb from obscurity to international fame, Cline captured the hearts of country music fans everywhere before her tragic death in an airplane crash in 1963, at the age of only 30. Her career culminated with her becoming the first solo female singer to join the Grand Ole Opry in 1960, and the first woman to be inducted into the Country Music Hall of Fame in 1973.
    The house was not open to the public when I was doing all my traveling between Maryland and North Carolina but it has now been restored and is open six days per week from April 1 through October 31, 2012. Schedule is changed twice each year.
    She is buried at the Shenandoah Memorial Cemetery in Winchester and the auditorium at John Handley High School, which she attended but did not graduate because she felt it necessary to leave school when her father deserted the family when she was 15. There is also an annual Patsy Cline Festival in Winchester on Labor Day weekend.

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    Visit nearby Harpers Ferry, West Virginia

    by Ewingjr98 Written Feb 18, 2009
    Harpers Ferry
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    Harper's Ferry, at the border of Virginia, Maryland, and West Virginia, and at the confluence of the Potomac and Shenandoah Rivers, was a strategic Civil War location with lots of history. Long before the war, Harper's ferry was established as a manufacturing and transportation center, as the US Armory and Arsenal was established in 1799. In the 1830s, this town hosted the Baltimore & Ohio Railroad, the Winchester & Potomac Railroad, and the Chesapeake & Ohio Canal.

    Before the war, John Brown's raid was a key event in the history of Harper's Ferry as his band of abolitionists attempted to seize the weapons at the armory to fight a guerrilla war in the south to free slaves. Once the war started the Federal troops destroyed the Harper's Ferry armory and weapons manufacturing machinery.

    During the war, the town changed hands 8 times, leaving much of the area in ruins. One key battle in September 1862 left 12,500 Union prisoners in the hands of Stonewall Jackson, allowing his forces to join the battle at nearby Antietam and prevent an even worse defeat.

    Today Harper's Ferry National Park is a popular tourist destination. It offers a unique historic village with shops and restaurants alongside historic buildings and ruins, all in a beautiful scenic location.

    Parking fee for vehicles in the lower town is $6, but you can leave your car at the park headquarters outside of town and ride the bus. The first time I visited, the town lots were full, but the second time in the winter there were several spots available. The battlefields are located outside of the central, historic town and have plenty of parking.


    In July 1859 John Brown, two of his sons, and others met in Maryland about seven miles from Harpers Ferry to begin creating an army and drafting plans to attack Harpers Ferry. They intended to seize the 100,000 rifles at he armory, then use them to arm lsaves throughout Virginia. On October 16, 1859, Brown and his 21-man "Provisional Army of the United States" took over the US Armory and Arsenal at Harpers Ferry in an effort to create an uprising among the slaves. Militia units and federal troops responded from surrounding areas, some led by future Confederate leaders Robert E. Lee and JEB Stuart. For the next two days several of John Brown's raiders along with numerous townspeople were killed as the raiders were gradually pushed from the Armory and Arsenal into the small firehouse in the far corner of town. Finally, on the morning of October 18th, twelve US Marines broke down the door of the Armory's firehouse, capturing Brown and the remaining raiders. In all, 17 people died including 10 of Brown's men.

    The 45-minute trial took place on November 2nd 1856, as Brown was charged with murder, conspiring slaves to rebel, and treason against the state of Virginia. He was sentenced to a public execution that took place on December 2nd, and was attending by VMI cadets led by Major Thomas J. "Stonewall" Jackson. John Wilkes Booth also witnessed the execution.

    It is said that the John Brown's failed raid raised tensions between the North and South the led to secession and the American Civil War.

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    Shenandoah River and Valley

    by Ewingjr98 Written Feb 17, 2009
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    The Shenandoah River runs 150 miles through western Virginia from Port Republic into the Potomac at Harpers Ferry. The lowest 20 miles of the river are in West Virginia, while the rest of the river and its tributaries flow through Virginia. Around Front Royal, the Shenandoah is famous for Canoeing and the city of Front Royal was named by the Virginia legislature as the Canoeing Capital of Virginia.

    The Shenandoah River Valley is bound to the east by the Blue Ridge Mountains, to the west by the eastern front of the Ridge-and-valley Appalachians, the town of Roanoke in the south and Harpers Ferry in the north. Some of the key cities in the valley include Staunton, Harrisonburg, Winchester, Lexington, Waynesboro, and Front Royal.

    During the Civil War the Shenandoah Valley a key agricultural region for the Confederacy was used as an attack route for Confederate raids on Maryland, Washington and Pennsylvania; because of this strategic importance it was the scene of three major campaigns.

    Over half of the land int he valley is used for farming and ranching. This is Virginia's top livestock region, as is apparent by the huge horse farms you'll see when driving through the area.


    Downriver Canoe Company, along with several competitors, offers canoe trips on the Shenandoah River, just outside of the Shenandoah National Park. The Downriver Company is located near the northern end of the park in the town of Bentonville, just 10 miles south of Front Royal, off US 340. We did a 7 1/2 mile trip from a starting point called "Burners Ford." As soon as you enter the water you encounter a set of Category I rapids... though small, they really surprised us and caused some difficulty and wet feet. At about halfway, you will hit a set of Category II rapids that you will hear long before you see. If you follow the Company's guidance and stay left, these will be exciting, but uneventful. Unfortunately, after these Cat IIs, the river is very calm and it offers no real challenges. The last mile or two gets almost boring as you have to paddle pretty hard to move at a decent speed.

    Throughout our trip, we saw dozens of turtles sunning on partially submerged logs, as well as a lot of fish. We also encountered some geese and a few farmer's cows who decided to enter the water just as we were going by...

    Cost per canoe is $39.00. It is enjoyable, especially for beginners, but the end of the trip is slow and somewhat boring.

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    Shenandoah National Park

    by Ewingjr98 Written Feb 17, 2009
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    When in Winchester, be sure to make the 30-minute side trip to Skyline Drive at Shenandoah National Park. The cost is $10 per car for one week of unlimited entry and exit. The feature of the park is Skyline Drive, a twisty, turny two-lane road that follows the ridge of the mountains providing countless breathtaking views to the east and west, along with wildlife, hiking trails, falls, and a few rest areas with snacks and souvenirs.

    Shenandoah National Park is a 105 mile long park that sits in Western Virginia between Interstate 66 to the north and I-64 to the south. The park covers almost 200,000 acres of unspoiled wilderness, with scenic, winding Skyline Drive running through the middle. Most of Skyline Drive is atop the ridges and has dozens of beautiful overlooks, quiet picnic areas, and peaceful hikes.

    Skyline drive is the centerpiece of Shenandoah National Park. It is controlled-access, meaning only vehicles which pay the $10 fee may enter. Though the price seems steep, it greatly limits the numbers of vehicles on this scenic and historic route. The 105 mile long roadway, running northeast to southwest has only four entrances, from north to south: Dickey Ridge off US Highway 340, Thornton Gap from US 211, Swift Run Gap at US 33, and Rockfish Gap at US 250 and Interstate 64.

    Skyline Drive is packed with overlooks, gaps, and picnic areas announced with fanciful names such as Bearfence Mountain, Little Stony Man, and Hogwallow. You will be hard pressed to find a 1/4 mile stretch with no pull-off areas. Food and gas are a little more difficult to find... the drive has about 5 areas with food and only 2 with gasoline. You may need to venture off the parkway to get necessities.

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    Old Town Winchester

    by Ewingjr98 Updated Feb 16, 2009
    Winchester Library
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    While Winchester has grown to some 25,000 people, the Old Town area is still a quaint small town that has lots of history and numerous businesses in focused on a small, old fashioned pedestrian mall. While the Loudoun Street Mall is the focus of Old Town, this area covers a four by four block area bordered by Washington, Fairfax, Clifford and Kent Streets.

    This are has four museums, nine churches, and businesses employing about 1800 people.

    Old Town has 210 parking spaces in lots, 400 on-street metered spaces, and 1,242 parking spaces in the three garages (with a fourth garage to be constructed).

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    Civil War history of Winchester

    by Ewingjr98 Updated Feb 16, 2009
    Court House Civil War Museum
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    The Shenandoah Valley was a crucial battleground early in the American Civil War, and Winchester, at the most accessible point of the valley, was the scene of numerous major battles and smaller skirmishes from 1861 to 1864. The more significant battles include the First Battle of Kernstown and the First Battle of Winchester in 1862, the Second Battle of Winchester in 1863, and the Second Battle of Kernstown and the Third Battle of Winchester in 1864. In all the town is said to have changed hands some

    The battles took place all around town and are marked by various historical signs. Some of these areas include Fort Jackson, Fort Alabama, Fort Collier, Louisiana Heights, and Bower's Hill. Jubal Early Drive runs south of downtown Winchester, along the central location for many of the battles. The Old Court House in downtown was used as a field hospital, and the Stonewall Jackson HQ stands on North Braddock Street. The Winchester National Cemetery holds the remains of over 5,000 Civil War dead, and it has numerous monuments dedicated to units that fought in the war.

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    Winchester's George Washington era history

    by Ewingjr98 Updated Feb 16, 2009
    Washington's Lot, Winchester

    The Virginia House of Burgesses chartered Winchester (as Frederick Town) in 1750, and George Washington arrived soon after to help survey the town's lands for England's Lord Fairfax. When General Edward Braddock crossed through Winchester on the way to Fort Duquesne in the French and Indian War, Washington joined the expedition as he was very familiar with the local lands; he became Braddock's aide-de-camp. In 1756 Washington constructed Fort Loudoun on about one acre of downtown Winchester on present-day Loudoun Street. Fort Loudoun was manned until the start of the Revolutionary War. Later during the French and Indian War (in 1758) Colonel George Washington was elected as a representative to the state's House of Burgesses.

    Years later, during the Revolutionary War, the same House of Burgesses chose local resident and Washington's French and Indian War colleague Daniel Morgan to raise a company of militia to support Washington's Siege of Boston. Morgan's Sharpshooters assembled in Winchester on July 1775 and marched to Boston in 21 days. Later Morgan was part of the disastrous Battle of Quebec where he and most of the Colonial force were captured and imprisoned for more than a year. After his release, Morgan was promoted to Colonel and he took part in numerous significant battles of the Revolution including Saratoga, Freeman's Farm, and Bemis Heights. after some time off from the war, he returned, was promoted to Brigadier General, and engineered the brilliant tactical victory over British Colonel Banastre Tarleton in the battle of Cowpens, capturing or killing almost all of Tarelton's 1,100 man unit, while suffering only 25 killed.

    Historic sites related to Washington and Morgan in Winchester include the Adam Kurtz House (called "Washington's Headquarters") and a lot with a historic plaque designating it Washington's lot. Daniel Morgan Middle School stands today in Winchester and Morgan's mansion--called Saratoga-- stands in nearby Boyce, VA. There are also various streets named after this era including Washington, Morgan, Loudoun, Braddock, Monmouth and Fairfax Streets.

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    Winchester's Pedestrian Mall

    by Ewingjr98 Updated Feb 16, 2009

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    Central Winchester has a great Pedestrian Mall the runs perhaps three blocks in the heart of the historical city center. On Loudoun Street it is completely blocked off two traffic, but cars are allowed on some of the side streets that are partially pedestrianized. This is the core business district of the historic area and it has numerous local restaurants, bars, shops, and other stores that are generally not national chains. To make up for the parking lost on this street, the city has erected at least three large garages all around the pedestrian mall.

    I was surprised to read that the Pedestrian Mall was created in 1974, and this was Virginia's first pedestrian mall.

    During our visit, we fell in love with this part of town. We stayed at the Washington Hotel nearby, ate at Brewbakers Restaurant, had drinks at the V2 Piano Bar, and had breakfast the next day runs outside of the Pedestrian Mall at the Piccadilly Grill. We also stopped by a few of the historic sites here, particularly the Old Court House.

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    Winchester's Old Court House & Feltner Building

    by Ewingjr98 Updated Feb 15, 2009

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    Court House and Civil War Monument
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    The historic Winchester Court House preexists the Civil War, but two previous court houses also share in the town's history.

    The first court house was constructed in 1741, and is considered the first courthouse ever constructed beyond the Blue Ridge mountains.

    The second court house was built on this site in 1758, and it was here that George Washington was first elected to public office--Virginia's House of Burgesses.

    The present court house was built in 1840 to serve the citizens of Winchester and Frederick County. This 1840 courthouse served as a prison and hospital during the Civil War. It served as the main courthouse until 1984 when the Frederick-Winchester Judicial Center opened. This site continued to be used for Frederick County meetings and offices until 1995, when city leaders decided the courthouse should be renovated and turned into a Civil War museum. The Old Court House Civil War Museum opened in 2003 and it houses numerous exhibits featuring writings by Civil War soldiers soldiers as well as some 3,000 artifacts of the war, ranging from buttons to cannonballs.

    In front of the Court House is a statue that is the town's Civil War Monument.


    The Feltner Building stands right beside the Court House and also has some interesting history. Most of the buildings here were constructed in the 1830s and 1840s, and they housed a local tavern, the local newspaper, and the county records storage room.

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    Glen Burnie Historic House - Highly Recommended

    by 807Wheaton Updated Jan 5, 2008

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    Visitors' Entrance
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    This is the home of Colonel James Wood, who settled here early in the 1700's and donated portions of his homestead to establish Winchester in 1744. The Glen Burnie site is now part of the Museum of the Shenandoah Complex, which includeds the house and informal gardens located on 6 acres. The 18th Century home is furnished with 18th and 19th century antiques. The paintings and decorative objects in the home are owned by Julian Wood Glass Jr. Sections of this Georgian red brick house date to 1794.
    After obtaining your admission ticket take advantage of the small exhibition that features an exact scale replica of the house and a video.
    The tour of the house is docent led and the gardens tours are self-guided. Wander through the garden and enjoy statuary and fountains.
    The site was opened in 1997. It is a great addition to the attractions in Winchester.

    When we took the tour I was impressed by the quality of the furniture and the art work that is housed there. You can probably spend about 2 hours looking at the house and the garden. There is a rose garden here that is lovely.
    Glen Burnie is open March through November, Tuesday through Sunday 10 to 4.
    Admission is $8.00 for an adult, $6.00 Students and Seniors.

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    Museum of the Shenandoah Highly Recommended

    by 807Wheaton Updated Jan 5, 2008

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    Museum of the Shenandoah, Winchester, VA

    The Museum of the Shenandoah and Glen Burnie are located on the same campus. The newly completed Museum is open year round.
    This complex offers a tour of a 18th Century historic house, six acres of beautiful garden and a museum that holds two spectacular collections of art and glassware.
    This is a first class venue and certainly something not to be missed when travel plans include a visit to Winchester.
    The attached web address really offers a great presentation of this complex.

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    Old Town Winchester

    by chewy3326 Written Nov 22, 2006

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    Winchester
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    I spent a minimal amount of time in Old Town Winchester, the downtown of this 24,000-person town, and I know I would like to spend more time here next time I visit. Winchester has some beautiful buildings and streets; there's a pedestrian mall, the Handle Library, a big apple, the City Hall, and some very beautiful churches. Winchester is a rather historic town; it was the site of a Civil War battle, and has some relatively-aged buildings, most from the early 1900's.

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    Hill High Farms Pumpkin Patch

    by chewy3326 Written Nov 22, 2006

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    Pumpkins

    The Pumpkin Patch is the main attraction of Hill High Farms. Each fall, pumpkins are harvested and often used by American families at Halloween. Visitors at the pumpkin patch can buy pumpkins at the main farm, or take a tractor ride out to pick their own pumpkins. Pumpkins abound; throughout Hill High Farms, you'll see plenty of orange.

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    Marker-Miller Orchards Farm Market

    by chewy3326 Written Nov 22, 2006

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    Marker-Miller Orchards Farm Market
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    Marker-Miller Orchards is another pick-your-own apple orchard. We did not do PYO here, we only went inside its large farm market. The market sells various produce (apples, peppers, peaches, etc), apple cider, donuts, cheese, pies, wine tasting, jams, etc. Marker-Miller also has pick your own peaches during July and August. PYO apples are $10.00 for half a bushel. You can also find pumpkins and take wagon rides on the farm. The Marker-Miller Orchard is considerably larger than the one at Hill High Farms.

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