Near the northern entrance to the Shenandoah Valley and sited at the crossroads of two historic foot trails, Winchester is the oldest Virginia city west of the Blue Ridge Mountains. Germans migrating from Pennsylvania did most of the heavy lifting in settling the region in the 1730s but the land belonged to the English lord, Thomas 6th Baron Fairfax of Cameron, part of his proprietary inheritance. In 1749 Lord Fairfax settled in the area that was called Frederick Town after Frederick, father of George III of England. To help figure out just what he had with his Virginia lands one of the surveyors that was hired was an eager red-headed lad by the name of George Washington, enthusiastically digging into his first paid job. Washington would build Fort Loudoun here 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.

The town’s named was switched to Winchester, honoring an ancient English capital, in 1752. It boasted a population approaching 1,000 and was the trade center of the valley on the Great Wagon Road from Pennsylvania to the southwest. There were many roads leading to ports where goods could be shipped to and from England. In the days after the Revolutionary War, Winchester led a charge to prosperity in America’s developing western lands. At one point merchants petitioned the Virginia assembly to build more roads and ferry boats, citing delays up to three days for freight wagons to get across the Shenandoah River.

By the mid 19th-century Winchester was a major supply route; the town lay on the Valley pike and was served by east-west and north-south railroads and the Potomac river. Not surprisingly, from the spring of 1862 until the fall of 1864 Winchester changed flags some 70 times. Four major engagements were fought in and around town. No traces of these battles, which helped drain Union resources away from a march on Richmond, remain.

Although more than 200 homes and buildings were destroyed during the fighting, Winchester shook off the ravages of the Civil War quicker than most Southern towns - mostly on the back of the apple. Winesaps, Pippins, Staymans, the Delicious, Black Twigs and, especially, York Imperials overflowed in some of the world’s largest packing houses. the Shenandoah Apple Blossom Festival began in the spring of 1924 to encourage folks to admire the hundreds of thousands of apple trees coming into bloom each year.

Our walking tour will visit a bit of Colonial history, a bit of Revolutionary War history, a bit of Civil War history and even touch on a bit of apple history and we’ll begin in the traditional center of town where folks used to gather for everything from a public hanging to Christmas caroling...  

1.
Frederick County Courthouse
center of Old Town Mall at North Loudoun Street

After conducting business in two previous log structures the courts moved into this large brick building with an imposing Doric portico, constructed to plans drawn by Baltimore architect Robert Cary Long, Jr. In 1840. The Greek Revival courthouse was the centerpiece of a judicial complex here that boasted eleven buildings, stocks, a whipping post and a pillory in the square.

WITH YOUR BACK TO THE COURTHOUSE IN THE CENTER OF THE SQUARE, TURN RIGHT AND WALK NORTH ON THE PEDESTRIAN MALL. 

2.
Farmers and Merchants National Bank
106 North Loudoun Street

The bank organized in 1902 with Confederate veteran and Winchester mayor Robert T. Barton at its head and this eye-catching Renaissance Revival building as its home. There is much going on architecturally with fluted columns interrupted by rectangular blocks, corner quoins formed from the golden bricks, rounded multi-paned windows in recessed arches on the first floor and pedimented windows above, fluted two-story pilasters and a wide overhanging eave but perhaps the most memorable feature of the three-story building is its fine corner

3.
Union Bank Building
101 North Loudoun Street

This Victorian brick building has been renovated back to its original 1878 appearance to become the standout property on the block. The Italianate facade is cast iron, a popular ornamental affect because of its cheap cost and east of forging the iron into decorative shapes. Despite those advantages, cast iron commercial facades are a rare find on America’s downtown streets 150 years later. This one was completely hidden behind a typical modernization until the restoration in 2009. 

4.
Hiram Lodge No. 21
118 North Loudoun Street

This Italianate style Masonic lodge was constructed with a stone facing in 1868. Its most interesting feature was added in 1901 when it picked up a carved stone pedimented Beaux Arts doorway. A copper bay projection on the second floor is also an attention grabber. 

RETRACE YOUR STEPS ON THE MALL BACK TO THE COURTHOUSE AND TURN LEFT. WALK PAST THE COURTHOUSE OUT TO CAMERON STREET. ON YOUR RIGHT IS...

5.
Rouss City Hall
15 North Cameron Street

Maryland-born Charles Baltzell Rouss moved with his family to Winchester at the age of 4 in 1840 and lived here until the Civil War, working as a store clerk as a young man. At first opposed to secession he apparently had a change of heart and joined the Confederate Army in 1864. He also placed all his money into Confederate bonds before joining. After the war he was deeply in debt and spent the best part of a year working on his father’s farm. In 1866 he moved to New York City where he spent time in debtor’s prison. After his release Rouss developed a specialty of buying distressed and auction merchandise for resale. He was successful enough by 1889 to build his own 10-story cast iron and stone on Broadway in the heart of New York’s shopping district. He changed his middle name to honor his new location and the Charles “Broadway” Rouss store stood ready to “make a man fashionable, a lady irresistible and a family comfortable.” His store would soon have branches across the globe - in Paris, Berlin, Nottingham, Vienna, Yokohama and Chemnitz. Rouss was generous with his millions, especially to Winchester, which he considered his hometown. His gifts built a fire hall, a hospital and the town hall. He built the wall around Mount Hebron Cemetery where he was buried after his death in 1902 in what was, at the time, the largest private mausoleum in the United States. 

TURN LEFT ON CAMERON STREET. TURN RIGHT ON EAST PICCADILLY STREET.

6.
George Washington Hotel
103 East Piccadilly Street at Cameron Street

This grand Georgian Revival guest house was built in 1924 by The American Hotel Corporation as part of there “Colonial Chain” of hotels. Like many hotels of the era, the property was built in close proximity of a B&O train station and was constructed to provide lodging to railroad passengers. the height of luxury in Winchester the five-story brick hotel featured 102 rooms and only 45 baths - welcome to 1920s travel. Over the years many famous names have signed the guest register, including Lucille Ball, Jack Dempsey among many others. The George Washington closed in the 1970s and for a time was converted to a home for the elderly. Recently revitalized, the hotel is once again welcoming guests. 

7.
B&O Passenger Depot
East Piccadilly Street at Kent Street  

The Winchester & Potomac Railroad was chartered in 1831 and connected to the Baltimore & Ohio Railroad in Harpers Ferry in 1837. In 1867 the Winchester and Strasburg Railroad began operations, also tying into the B&O in Harpers Ferry. Eventually all track fell under the umbrella of the Baltimore & Ohio which erected this picturesque stone-and-wood passenger depot in 1893. The Victorian station retains its decorative brackets and exposed rafter ends supporting a wide overhanging eave. The irregular hipped roof is decorated by a tower, a cupola and eyebrow vents. The tracks are still active but trains no longer stop here. 

TURN AND RETRACE YOUR STEPS ON EAST PICCADILLY, CROSSING OVER CAMERON STREET.

8.
Commercial and Savings Bank
186 North Loudon Street at East Piccadilly Street

Presenting a formidable entrance to the pedestrian mall, this Neoclassical stone building was completed in 1900 for the Commercial and Savings Bank. The central recessed bay is flanked by stout Doric columns and the large, arched windows are delineated by giant order pilasters. The building still serves as a banking house today. 

9.
Shenandoah Valley National Bank
201 North Loudoun Street at Piccadilly Street 

The Shenandoah Valley National Bank took its first deposits in January 1866 and moved into this Beaux Arts vault in the first years of the 20th century. The three-story corner anchor features a first floor of coursed ashlar and thin bricks above. The upper floor bays are defined by brick Corinthian pilasters and are highlighted by decorative sculptures. 

10.
Williams House
25 West Piccadilly Street

Phillip Williams, Jr., Commonwealth Attorney for Shenandoah and Warren counties during the mid-1800s built this Greek Revival, five-bay house around 1845. It stands out today for its decorative cast iron work, including a three-bay porch and property fencing. 

11.
Reed House
35 West Piccadilly Street

This rubble stone house is a relic of the 19th century, constructed by the Reverend George Reed between 1797 and 1800. Irish-born Reed was an early leader in the Methodist church in Winchester and later mayor of the town and high sheriff of Frederick county. He also owned a coppersmith shop next door to the west. The main wing is a solid example of a late-Georgian/ early American stone house. In its 200 years the former residence has done duty as an art gallery, commercial space and a bank before moving into its third century as a private residence once again. 

12. 
Old Post Office
40 West Piccadilly Street

This federal building was constructed in 1910-11 under the direction of James Knox Taylor, Supervising Architect of the United States Treasury. The building is highlighted by stone Ionic columns that support a full entablature. Stone swags in rectangular panels decorate the brick walls between the porch bays. The building serves private commercial use today. 

13.
Handley Regional Library
100 West Piccadilly Street at Braddock Street

John Handley was born in Ireland in 1835, became a U.S. citizen in New York in 1856, and eventually moved to Scranton, Pennsylvania where he practiced law and was an influential judge. It was said that he was a strong sympathizer of the South during the Civil War and is thought to have first visited Winchester in 1869 where he developed many friendships. So much so that when he died in 1895 he made the town the residuary legatee of one-third of his estate, engorged from investments in Pennsylvania coal and estimated at $4,000,000. It was a big enough story to be reported in the Baltimore Sun and New York Times, which wrote, “Winchester deserves all this good luck. It is a city ‘beautiful for situation,’ and its population is one of the most intelligent, industrious, and refined to be found anywhere.” Handley reserved $250,000 for the construction of a free public library and architects J. Stewart Barney and Henry Otis Chapman of New York designed an exuberant tour-de-force in the Beaux-Arts style. When the Handley Library opened in 1913 the final bill for building and furnishings was $233,230.28. Its L-shaped design is meant to mimic an open book with the elaborate domed corner entrance serving as the spine.

TURN RIGHT BRADDOCK STREET.

14.
Stonewall Jackson’s Headquarters
415 North Braddock Street 

Thomas “Stonewall” Jackson made his Civil War headquarters in the small Gothic Revival cottage between November 1861 and March 1862. The house was built in 1854 by William Fuller who later sold it to Lt. Colonel Lewis T. Moore of the Fourth Virginia Volunteers. It was Moore who extended the offer to use his home as Headquarters to General Jackson. One of Colonel Moore’s descendants is actress Mary Tyler Moore, who has helped pay for restorations of the home for the museum - including replica wallpaper matching the original of which Jackson wrote enthusiastically. 

TURN AND RETRACE YORU STEPS ON BRADDOCK STREET AND CONTINUE ACROSS PICCADILLY STREET.

15.
Logan House/Sheridan’s Headquarters
135 North Braddock Street at Piccadilly Street 

This stately Greek Revival home was erected in 1850 by Lloyd Logan who made his money peddling tobacco. The building served as headquarters for General N.P. Banks in 1862, for General R.H. Milroy during the next year and Union General Phillip Sheridan directed his Second Valley campaign from behind the imposing Corinthian columns of this house. On October 19, 1864, Sheridan began his famous ride to Cedar Creek from here to rally his troops to victory. After the town’s first Shenandoah Apple Blossom Festival in 1924, a five-foot concrete and plaster apple was purloined from a parade float and placed in the yard. That original has since rotted but it has been replaced and spawned the painted apples you see decorated by local artists around Winchester. 

TURN RIGHT ON WEST BOSCAWEN STREET.

16.
Christ Episcopal Church
114 West Boscawen Street 

A rudimentary wooden church for the Church of England was constructed in the wilderness in the 1740s and it served the area’s Episcopalians until about 1766 when a suitable stone church was erected, considered one of the finest pre-Revolutionary buildings in Winchester. By the 1820s, however, the congregation was clamoring for a more substantial meetinghouse and the cornerstone for this building was laid on June 24, 1828. John Bruce is credited with designing the early Gothic Revival church. The square tower was a later addition. Beside the church is the brick tomb of the original landowner of Frederick County, Lord Fairfax.

TURN AND RETRACE YOUR STEPS ON BOSCAWEN STREET. 

17.
Charley Rouss Fire Company
3 South Braddock Street at Boscawen Street

Winchester’s Union Fire Company is believed to have organized in the 1780s , although company records were, ironically, destroyed in a fire in 1858. In 1895 Charles Broadway Rouss donated $5,000 for a new fire hall and this Romanesque-inspired brick building was the result. Afterwards the company became The Charley Rouss Fire Company and today is one of four volunteer fire companies in the City of Winchester. For much of its existence the fire house has been topped by a molded-copper fireman weathervane known as “Old Jake.” Measuring over 6 feet high and 6 feet wide, “Old Jake” was dismounted from his perch above the Winchester skyline in 2008 and put for sale by Sotheby’s auction house. Expected to bring between $3 million and $5 million, the high bid came in a tick over $2 million and the sale was withdrawn. “Old Jake” is currently in the Museum of the Shenandoah Valley and a replica may once again crown the Rouss Fire House. 

CONTINUE ON BOSCAWEN STREET ACROSS BRADDOCK STREET. 

18.
Grace Evangelical Church
26 West Boscawen Street 

The German Lutherans who settled in the valley laid a cornerstone for their first church building on April 16, 1764. It would remain standing until 1854 when a sparks from a nearby stable incinerated the property; the remains of the stone walls stand today in the church cemetery. The present structure was constructed as a meeting hall in the Greek Revival style and later converted to Gothic Revival for ecclesiastical purposes. The congregation added a Gothic Revival to the west in the 1920s. A carillon of ten bells placed in the belfry was installed in 1917 in the memory of David Brevitt Glaize.

TURN RIGHT ON LOUDOUN STREET, BACK ONTO THE OLD TOWN MALL.

19.
Godfrey Miller House
8 South Loudoun Street 

This finely crafted gray stone Georgian style house was built in 1785 by Daniel Sowers; Lord Fairfax granted him the land back in 1753. It was purchased by merchant Godfrey Miller in 1850 and today is operated as an historic house.

20.
First Presbyterian Church
116 South Loudoun Street

The tentacles of the Presbyterian Church in the northern Shenandoah Valley reach back into the 1730s. In 1826, a church building was erected at the corner of Kent and Boscawen streets. In 1841, the congregation built a Gothic Revival “lecture room” here that was the beginning of a permanent home for First Presbyterian Church. The tower is topped by a crowning pinnacle with accompanying pinnacles on the corners of the crenelated parapet. 

21.
Hill’s Keep
126 South Loudoun Street

This vernacular stone building was constructed on East Cork Street around 1810. it was relocated here in 2004. 

TURN RIGHT AT THE END OF THE MALL ONTO CORK STREET. 

22.
Vostrikov’s Academy of Ballet
20 West Cork Street

This large Neoclassical brick building was constructed in 1924 for the Cork Street Christian Church. Since 1982 it has been the home of the Vostrikov Academy of Ballet.

23.
George Washington’s Office
northeast corner of South Braddock Street and West Cork Street 

In Winchester, long a crossroads town at the head of the Shenandoah Valley, George Washington began his surveying career in 1748, working under Lord Thomas Fairfax. Washington eventually staked out much of the prime land on the Virginia frontier for himself and family members. Later, as a landlord, he required each tenant to plant atleast four acres of apples. Washington returned to Winchester in 1755 to supervise the construction Fort Loudon; he used this small building as his office for the next 15 months. The newer part is built of rough stone, the older of hewn logs covered with clapboards. He remained in Fort Loudon as commander and was twice elected to represent Winchester in the Virginia House of Burgesses, in 1758 and 1761..   

TURN AND RETRACE YOUR STEPS ON CORK STREET, HEADING EAST AND CROSSING LOUDOUN STREET.

24.
Red Lion Tavern
southeast corner of Cork and Loudoun streets

Pennsylvania native Peter Lauck returned from the Revolutionary War, where he was captured in the Battle of Quebec, to build this two-story limestone tavern in 1783. He was not an owner-operator but leased the Red Lion to a succession of proprietors. The original grant of land on which the Red Lion Inn is situated, is written on parchment and bearing the signature of Lord Fairfax. George Washington was known to have stopped here several times. 

25.
.Friendship Fire Hall
10-12 East Cork Street

This brick building was constructed in 1831 and modified into an Italianate-styled firehouse for the Charley Rouss Company in 1892, highlighted by a square 2 1/2-story tower. The first floor central bay contains a large garage door marked by vouissoirs and keystone detailing. The windows present variations of Federal-style sunburst fanlights.

26.
John Kerr School
203 South Cameron Street at East Cork Street

When it was completed in 1883 the John Kerr School ended the peripatetic existence of the Winchester public school system that had rented space in buildings across the town. Kerr donated half of the $20,000 construction cost for the large Italianate-flavored building. A native of England, he came to Winchester about 1825 in his early twenties and found work as a cabinet-maker. John Kerr died childless in 1874 and left his property to provide a schoolhouse for the children of his adopted town. The building went through major renovation in the early 80’s and is now managed by Shenandoah University. 

27.
Centenary Reformed United Church of Christ
202 South Cameron Street at East Cork Street

Centenary was the first church built in Winchester, about 1749, served by horseback riding circuit preachers. A brick church was erected on this spot in 1842 to celebrate the centennial of the founding of the congregation in the Shenandoah Valley. Union soldiers torched the church during the War Between the States and the current rebuilt Gothic Revival structure was dedicated in 1906. The museum, featuring the largest collection of Confederate artifacts in the world, moved into the adjacent building in 1976. Artifacts from every important Southern leader, including Lee’s surrender sword at Appomattox, are on hand. Also on display is the last Confederate flag, flown by the CSS Shenandoah, a warship harassing a United States whaling fleet in the pacific Ocean when the war ended. Unaware of the fall of the Confederacy until August, the crew then sailed 17,000 miles around Cape Horn to England, finally surrendering to the British on November 6, 1865. 

TURN LEFT ON CAMERON STREET. 

28.
Market Street Methodist Church
131 South Cameron Street

This is the third house of worship for the Winchester Methodists who trace their beginnings to 1772 when circuit riders William Watters and Richard Wright preached here. James Walls, a local carpenter, started the first congregation of eleven members in 1789. The two-story Classical Revival church was dedicated on May 20, 1855. Tall windows in each front bay are topped by a bracketed entablature and brick pilasters support Corinthian capitals and a richly carved pedimented entablature.

29.
Star Building
37-45 East Boscawen Street at Cameron Street

Winchester got its first daily newspaper on January 12, 1895 when John I. Sloat put out his first edition of the Evening Item. Sloat was a mere lad of 21 who had learned the printing trade in the employ of Howard Gosorn who operated the Winchester Leader, a weekly organ of the Republican party. Sloat’s four-page daily was successful enough that he was shortly able to sell the Item to Bernard Wade, editor of the Winchester Weekly News. And then Sloat went right back to press and debuted the Evening Star on July 4, 1896. His new daily was now competing with his old daily - and did so for more than a decade until the two papers merged in 1907 under the Star masthead and has continued so for more than 100 years. This brick building was constructed in the 1830s and given an Italianate makeover in the 1890s. Each first floor bay contains a double door entrance with a fanlight and all the windows are spotted by a small keystone. This was the offices of the Winchester Item and the Star occupied the space from 1910 until 1946 when the offices moved over to the Kent Street corner. 

30.
Kurtz Building
2 North Cameron Street at East Boscawen Street

This Federal-style building was erected in 1836 by a group of businessmen from Harper’s Ferry to house grain before shipping it on the new railroad to the mills in western Virginia. George Kurtz bought the building in 1876 and adapted it to use for his furniture business. Alterations included a fashionable Second Empire mansard tower and cast-iron cresting along the roof. The Kurtz family sold the building to the city in 1968 and it resisted demolition and modernization to emerge as a restored property.  

TO CONCLUDE THE TOUR WALK UP A FEW STEPS TO CITY HALL AND TURN LEFT OR TO VISIT THE HISTORIC 250-YEAR OLD COMMUNITY CEMETERY, TURN RIGHT ON EAST BOSCAWEN STREET AND WALK TWO BLOCKS.

Detour Stop:
Mount Hebron Cemetery
305 East Boscawen Street 

This complex of four adjoining burying grounds started in the 1760s as the churchyard of the old Reformed Church. Next door was a small acre-and-a-quarter cemetery of the Lutheran Church. In 1844 five acres were acquired for a graveyard dubbed Hebron after the biblical city that provided refuge to Abraham. A fourth contiguous burying ground was dedicated in 1866 as the Stonewall Cemetery for the bodies of 2,576 Confederate soldiers who died in the fields and hospitals in the Shenandoah. The tall shaft in the center of the graveyard honors 829 unknown soldiers; it is one of the earliest Civil War monuments, dedicated in 1866.

The most esteemed Mount Hebron resident is Daniel Morgan who began his military career alongside George Washington in the service of Edward Braddock in the French and Indian War. In the American Revolution General Morgan covered himself with glory whenever he took the field - in the assault at Quebec, in the defeat of Burgoyne at Saratoga, in the crushing of Tarleton at Cowpens. He was the most renowned rifleman of the Revolution.

In 1779, in nearby Boyce, he began work on an impressive mansion that he named Saratoga. much of the work was performed by Hessian prisoners. In the decade after the Revolution Morgan acquired over a quarter-million acres of land through speculation, becoming one of the most powerful men in the Shenandoah. In 1797 he was elected to congress, but ill health, which hampered him throughout his military career, limited him to a single term. When he returned to western Virginia, encroaching lameness forced him to abandon Saratoga in 1800 and live on Amherst Street in Winchester. He died in 1802 at the age of 66 and is buried along with five members of his Revolutionary bodyguard near the entrance at East Boscawen Street.