8 32 W. Cork St. George Washington’s Office Museum (c. 1748) 17 18 , In 1748, sixteen year PICCADILLY old George Washington 16 19 30 275 Years of 20 arrived in Winchester 21 P as a surveyor. In 1753, 22 he became an officer 13 15 23 HISTORY & in the Virginia militia. AMHERST P Based on local tradition, 14 24 25 27 from 1755-1756 this 26 ROUSS vernacular log and 1 28 stone cabin served as Col. Washington’s headquarters 11 29 Architecture during the French and Indian War. The building is BOSCAWEN operated as a museum by the Winchester-Frederick 12 10 9 2 Old Town P County Historical Society. The statue of young George Welcome Washington as a surveyor was erected in 2004. Center 3 At the corner of Cork and Braddock St. turn right and ON 4 proceed northward. WOLFE

Winchester continued to grow and prosper during the ON 5 19th century. Frederick County was one of Virginia’s ASHING T W largest wheat producing counties and Winchester was a 6 AME R bustling trade and commerce center. Although Federal- 8 C style buildings remained popular, other styles emerged CORK To Visitors Center such as Greek Revival (1840 to 1860) and the Victorian 7 N era style (1837 to 1901), including Gothic Revival, = PARKING Italianate, Second Empire, and Queen Anne. These new P styles were used for both public and private buildings and HISTORIC ADDOCK = MARKER OUDOUN

S L for “updating” existing buildings. B R Proceed to intersection of Braddock and Boscawen Streets. This walking tour brochure was originally proposed by Preservation of Historic Winchester, Inc. 3 S. Braddock St. Rouss Fire Hall (1896) 9 This version was produced by: This prominent landmark was built with funds from one of Winchester’s benefactors, Charles B. Rouss, a successful local merchant who later relocated to NYC, where his national chain of general merchandise stores made VisitOTW.com VisitWinchesterVA.com him a multi-millionaire in the late 33 E. Boscawen St, 1400 S. Pleasant Valley Rd, 1800s. The building is a fine example Winchester Winchester of the Romanesque Revival style (1880 to 1900). The distinctive Special thanks to Sandra Bosley, Preservation of Historic weathervane on top of the turret is Winchester and Tim Youmans, City of Winchester for a facsimile of the original. their contributions to this brochure. Photos courtesy of Preservation of Historic Winchester and Turn left and proceed westward on Boscawen St. Winchester-Frederick County Convention and Visitors Bureau

Self-Guided WALKING TOUR

WE HOPE YOU ENJOY THIS 2 2-4 S. Loudoun St. The Holliday House (c. 1797) 5 116 S. Loudoun St. First Presbyterian WALKING TOUR HIGHLIGHTING Originally this building was a two-story Federal- Church (1841 Remodeled in 1883) style Flemish-bond brick building with “glazed 275 Years of Old Town Winchester’s headers,”- the shiny narrow ends of the brick. The glazed Begun in 1841, the headers are best seen on the Boscawen St. side. Italianate edifice has evolved HISTORY & alterations in the 1860s included a third floor, window into a Gothic Revival hoods, a bracketed cornice and corner entry. It was built style structure with Architecture a 3-story steeple inchester’s first European settlers were German by William Holliday, a successful merchant, and remodeled by his heirs. His grandson, Frederick William Holliday, flanked by two 2-story W and Scots-Irish migrating south from Pennsylvania was elected governor of Virginia. towers topped with in the 1730s. Originally known as Opeckon and then battlement and as Frederick Town, Winchester was founded in 1744 by Cross Boscawen St. and continue southward down the mall to 21 S. Loudoun St. corner capitals. See James Wood – the first English-speaking town interpretive panel on established west of the Blue Ridge Mountains. It was re- In the days before the American Revolution, Winchester site for more info. named Winchester in the early 1750s. Winchester was part was the center for commerce and culture west of the Blue of a 5 million-acre tract of land known as the Northern Ridge Mountains. Typical 18th century houses were built Neck, granted by ’s King Charles II to ancestors of of either log or stone. The structures were primarily used Thomas Lord Fairfax in 1647. When Lord Fairfax came to for shelter without much regard for fashion. The American America in 1747, he found his land already being settled. Revolution brought a halt to new construction. Following 6 126 S. Loudoun St. Hill’s Keep the war, a delicately detailed and gracefully proportioned (1810 Moved 2004) He asserted his rights by requiring those who occupied his Federal style emerged and many excellent examples remain domain to pay rent and obtain licenses for their land. in Winchester today. This small restored one-story vernacular BEGIN SEE MAP ON BACK 3 21 S. Loudoun St. James Dowdall Residence limestone building was HERE FOR LOCATIONS (c. 1792) relocated from 8 E. This limestone house Cork to make room for a church fellowship 1 20 N. Loudoun St. Old Frederick is a beautiful example County Courthouse (1840) of Federal style hall and is believed to architecture. Of be where the man- The first courthouse reputedly particular note is the servants of those who constructed on this location was arched tracery stayed at the Red Lion Tavern (tour stop 7) were billeted. built of logs in 1751. At this site on transom over the Proceed south to the end of the Pedestrian mall at Cork St. July 24, 1756, 23-year-old George doorway and stone and without crossing the street, view the corner limestone Washington began his political career. jack arches with building on the opposite side of Cork St. He was elected to public office for the keystones. The original building on this site was Cocke’s very first time and served two terms Tavern where George Washington lodged and took meals. 202-204 S. Loudoun St. Red Lion Tavern The current stone building was built by James G. Dowdall, 7 2 as the Frederick County representative (1783) to the Virginia House of Burgesses. This existing courthouse a prominent merchant and city official. was built for $12k. It is one of the most impressive Greek The Red Lion Tavern Revival-style courthouses in Virginia. It is currently 4 28 S. Loudoun St. Godfrey Miller Home was built by Peter occupied by the Civil War Museum. (c. 1785) Lauck, a member This house was built of ’s Proceed south to the intersection of the Loudoun Street by Daniel Sowers. It riflemen. The north Mall and Boscawen St. was sold in 1850 to section of the building The Great Wagon Road, part of which extended along Godfrey Miller, a was the tavern and what is Loudoun Street today, was the main roadway merchant, and in the south part was the leading through the Shenandoah Valley. The original town 1938 his heirs willed inn. plan devised by Col. James Wood in 1744 had 30 half-acre it to Grace Lutheran Church to be operated lots, 26 for dwellings or shops, and 4 for public use Turn right (west) on Cork St. stopping at the George as a home for elderly ladies. It now serves as a senior center. Washington statue. including the courthouse, church and jail. The public lots The dentil cornice and stone jack arches with keystones were located on the northeast block of this intersection, above the windows exemplify fine details popular with the TOUR CONTINUES which is the oldest in town. In 1752, Lord Fairfax added Federal style. The Greek Revival-style porch with paired ON BACK 36 in-lots and 80 out-lots to the north. Tuscan columns was added by the mid-19th century. 10 125 W. Boscawen St. Josiah Massie Hatter’s 135 N. Braddock St. Logan House (c. 1850) 107 N. Loudoun St. Miller’s Drug Store (c. 1820) Shop (c. 1810) 16 24 Lloyd Logan, a wealthy tobacco merchant, built Godfrey Miller II built this Federal-style building. This restored vernacular building is an excellent example this Greek Revival house. Union General Milroy used this The building was known as the oldest continually operated of Winchester’s early log dwellings. Rather than leave the as his headquarters in 1862. It was headquarters for Union family-run drugstore in America until it closed in 1992. logs exposed, the buildings were covered with wood General Philip Sheridan in 1864. The massive two-story The front portion was added to an 18th-century flounder weatherboard siding. This structure was built by John front porch was added early in the twentieth century along style home. Nephew George Miller, the second owner, Slagle and was used until 1829 as a hatter’s shop. with the large concrete red apple installed by the Elks club expanded the business to an apothecary and dry goods Continue westward stopping in front of the church courtyard. which used the building for many years. store. Original ledger box, medical books, and supplies, dating back to 1806 were buried under a staircase. They 11 140 W. Boscawen St. Christ Episcopal 17 100 W. Piccadilly St. Handley Library were discovered in 1992 and have been preserved. Church (1828) (1908-1913 Rear addition 1979) This church is an early The Handley Library 25 100 N. Loudoun St. Farmers and Merchants example of Gothic was designed by New Bank (1902) Revival architecture. architects Stuart This Italian Renaissance Its design was Barney and Henry Revival structure was attributed to local Otis Chapman. It is built for the Farmers Scottish builder, John an excellent example & Merchants Bank. Bruce; however, of the Beaux Arts style Renovated in the Robert Mills, one of (1890-1920), which is 1990s, it was later America’s first trained characterized by owned and operated architects, may have extravagant sculptural ornamentation and architectural by BB&T Bank until developed the original details drawn from the European Renaissance. The sold in 2017. Note design. The tower and building features a copper dome rising above the colonnaded the beautifully fifth bay were added entry vestibule with fluted Corinthian columns. The original detailed façade including brick quoins, fluted concrete after 1852. The two building design resembles an open book with the rotunda pilasters, cartouches, massive overhang, arched windows, vestibules were added as the spine and the two wings the open covers and pages. pedimented windows and many other architectural details about 1900. Note the fine Gothic features: crenellated bell Although never a Winchester resident, Judge John Handley unique to this building. tower, pointed arch tracery at windows and transoms, and of Scranton, Pennsylvania, bequeathed the City $2 million spirelets topping each corner. Lord Fairfax’s tomb is located 101 N. Loudoun St. Union Bank Building for construction and operation of this public library and 26 (1870) in the church courtyard. Lord Fairfax took an active role in two schools. During business hours, the beautiful interior community affairs. Although he lived at Greenway Court rotunda complete with stained glass ceiling can be viewed. This tall two-story many miles east of Winchester, he was buried at the site of building is a commer- the original church (now a parking lot near Stop#2) and, cial example of the after three reinternments, is buried here. 18 40 W. Piccadilly St. Old Post Office (1910) Classical Revival style. Proceed to the corner of Boscawen and Washington Streets. This former post office The lower level façade As you look southward (left) down Washington St., you is a fine example of includes historically can see the residential pattern that emerged in the 1890s the Classical Revival- accurate reproductions with houses set back from the streets surrounded by large style (1890 to 1925) of details that had yards. This Washington Street is almost certainly the very which, like the been destroyed during first street ever named for young George Washington by Beaux-Arts style, used a 1960s jewelry store his friend, Winchester’s founder, Col. James Wood. classical motifs, but modernization effort. with a more refined The upper level original façade had been left 1 S. Washington St. The Gables (1899) and restrained 12 application. Note the concrete panels with garland sways intact behind a modern “The Gables” is above the front door and four adjacent windows. aluminum skin that Winchester’s most Turn right on Piccadilly St. and proceed eastward. was removed in the exuberant Queen 1990s. Can you find the two lion’s heads up near the top? Anne-style house. It 19 35 W. Piccadilly St. George Reed House (1797) Turn left in between 100 N. Loudoun St. and the court- was the home of W.H. This vernacular stone house was constructed by house and proceed east on Rouss Ave. (the brick plaza). Baker, who was sued George Reed, a coppersmith who had a shop immediately for trademark adjacent to the corner of Piccadilly and Braddock Streets 30-38 Rouss Ave. Lawyers Row (1872) infringement by the (since demolished). The building is typical of early Winchester 27 nationally renowned stone buildings - two stories with two rooms per floor. Known as “Lawyers Row”, this building was W. Baker’s Chocolate constructed by Frederick W.M. Holliday just before he Company. The house displays the variety of materials, 25 W. Piccadilly St. Philip Williams House (1845) became governor of Virginia. Its location near the court- textures, colors and shapes characteristic of the Queen 20 house made it a popular location for law offices. Two This Greek Revival-style house was built by Philip historical nameplates still appear on the single-story Anne style. George Franklin Barber, a prolific late Victorian Williams, a local attorney and former member of the VA era architect, designed this house and used the Gables as a addition to the east. Italianate in style, the details are House of Delegates. The elaborate ironwork porch, decorated restrained and only the porch brackets, bracketed cornice, template in a pattern book with an estimated construction with Greek motifs, is of excellent quality and quite unusual and carved frieze could be termed “fancy”. cost of $10-$12k. for this area. The apple sculpture to the right includes Turn right and head northward on Washington St. Turn images of Polar Explorer Admiral Byrd, George Washington, left on Amherst Street and proceed up the hill. 226 Gen. Jubal Early, Col. James Wood, and . 28 15 N. Cameron St. Rouss City Hall (1901) Amherst is the large white house on your right and 223 Proceed east and turn right onto the Loudoun Street Mall. This impressive fully Amherst is across the street. In the late 19th and early 20th centuries, Winchester’s renovated public economy was largely supported by the apple and wheat 13 226 Amherst St., Daniel Morgan House (1786) industries, woolen mills and a variety of other businesses. building combines The front right timber frame portion of this All but three of the buildings at this end of the mall were elements from many Georgian style house was built by George Flowerdew built prior to 1900. Many changes were made to the styles. The arched Norton. In 1800, a revolutionary war hero, General Daniel buildings over the years to adapt them for commercial use. windows and recessed Morgan, purchased it and built a large brick addition. Before becoming President, William McKinley was in entries reflect Richard- Following the war, Morgan served as a U.S. Congressman. Winchester as a Union officer in the Civil War. He became sonian Romanesque He retired to Winchester in 1800 and died here in 1802. a mason in a building since demolished on the east side. A Revival style. The The house was covered with stucco by 1850. bronzed plaque is attached to the side of 186 N. Loudoun. hood mold over the upper level windows reflects English Gothic style and the slate roof, clock tower, and dormers 14 223 Amherst St. Ambler Hill (1786) 21 163-165 N. Loudoun St. Lovett Building (1881) reflect a Victorian style. Finally, the minimalist detail on John Hatley Norton, George Norton’s brother, This building is one of Winchester’s best examples the walls and window bays reflects the Classical style. It constructed Ambler Hill concurrent with the Daniel of Italianate-style with Eastlake ornamentation. The was built for $62k with $30k of that amount given by Morgan House. Both Georgian style homes feature frame striking massive wood cornice is one of the finest to be NYC benefactor Charles B. Rouss who grew up in peg construction with brick nogging between the studs in found in Winchester. Winchester and operated his first store here. their original sections. The home is also the birthplace of In the 19th century, Cameron St. (then known as ‘Market 146 N. Loudoun St., Mesker Building (c. 1880) Virginia novelist John Esten Cooke (1830-1886). 22 St.’) was where the Market House was located. Demolished Turn back and head eastward along Amherst St. Cross The intricate detailing in 1899, it was where City Hall is today. Washington St. and stop. on this Italianate-style This block appears today much as it did in the mid-19th building’s upper story, 29 2 N. Cameron St. Kurtz Building (1836) century. 138 Amherst, a well-restored Federal style house including the massive Investors built this warehouse to house a grain was built around 1835 by Alexander Tidball, a prominent metal entablature at purchasing business and shipped grain to Harper’s Ferry attorney. Note the old building-mounted street signs on the top is the only via the railroad which ran down the center of Cameron St. 138 Amherst Street. 132 and 124 Amherst were constructed known example of a In 1888, Captain George W. Kurtz added the mansard- around 1870 by Dr. Hugh Holmes McGuire, brother-in- Mesker Bros. metal façade design in Winchester. Pressed roofed tower and Victorian embellishments. He used the law of Alexander Tidball. 123 Amherst, a brick house with metal sheets with floral and decorative patterns could be pebbledash, was built in 1820 by Eli Beall, a schoolteacher. building for a furniture and funerary business. In 1989, applied for a quick “facelift.” The circa 1897 metal façade Preservation of Historic Winchester Inc. rescued the building Proceed eastward along Amherst St. to the intersection and may have been a sales tactic for the tinsmith who occupied from demolition and restored the exterior and interior. turn left onto Braddock St. this building circa 1890-1908. Proceed north on Cameron St. and turn right on Piccadilly St. 15 103 N. Braddock St. McGuire House (c. 1820) 23 121-125 N. Loudoun St. Taylor Hotel (1836) 30 103 E. Piccadilly St. George Washington This substantial The Federal-style Hotel (1924) Georgian style brick Taylor Hotel, owned This restored Georgian house was the home by Bushrod Taylor, Revival-style hotel of Dr. Hugh Holmes was once one of the displays a creative use McGuire, who founded most elegant hotels in of contrasting the very first medical Winchester. See materials to lend college in Virginia in adjacent Civil War interest to its large 1826 in a building at marker for more info. facade. Molded the rear of this house. Guests include Henry concrete is used in the It was the boyhood home of Hugh’s son, Dr. Hunter Clay, Daniel Webster, bracketed cornice, Holmes McGuire, “Stonewall” Jackson’s personal physician Turner Ashby, and Stonewall Jackson. The center section arches and keystones are above every window, and during the Civil War. Just up Braddock St was home of of the building which housed a theater collapsed in 2007. decorative molded garland panels and ornate overhang at Betsy Taylor Dandridge. She was the daughter of U.S. That led the City to initiate a public-private effort in 2012 the front entry. Pres. Zachary Taylor and served as First Lady to her father. to preserve the theater fly tower (c. 1921) and front hotel END OF TOUR Proceed northward along Braddock St. building, including a reconstructed three-story porch.