Introduction
A vital marketplace for more than 250 years, Old Town Winchester is located within the heart of a 45-block National Register Historic District and features a quaint pedestrian walking mall bursting with outdoor cafes, fun & specialty retail shops, historic attractions and family-oriented activities throughout the year.The Loudoun Street Pedestrian Mall has earned a listing on the National Register of Historic Places Travel Itinerary. A 7 million dollar renovation of the Mall was completed in 2013.
39 E. Piccadilly Street (Four Square Architects)
The building's first tenant, The Flower Shop, opened its doors in November 1938, operated by the Miller Brothers, Herbert W. Miller and Leonard I. Miller. Prior to moving here, the Millers had been in business for 20 years at 11 W. Piccadilly Street (inside the Hotel Jack). Their florist business was the oldest of its kind in the Shenandoah Valley, with flowers sourced from their 18,000-square-foot greenhouse on Martinsburg Pike.Designed to be the most modern florist shop in Virginia at the time, 39 E. Piccadilly featured: A polished black vitrolite façade Large oval mirrors in the showroom An interior color scheme of cream and dark green (which inspired the building’s current green accents) A walk-in cooler with a Jamison C.S. Door Co. heavy-duty wooden door from Hagerstown, Maryland (still present today) A rear greenhouse added shortly after opening (which still exists)Construction was handled by Howard Shockey & Son, with interior details provided by local businesses: Armstrong flooring from The House Furnishing Shop Iron Fireman coal burner installed by Miller & Anderson Plumbing & Heating Signage and lighting by Southern Neon Sign Service of HarrisonburgThe Miller Family Legacy and TransitionAfter Herbert Miller’s passing, the shop was inherited by his son, William (Bill) H. Miller, who found himself unexpectedly running the family business while managing his parents' medical debts. Meanwhile, his sister Jean used her inheritance to study art abroad, selling the family home on Cork Street, which was later demolished for a hospital parking lot.In 1977, Gilda O. Lemley took over the business with Eva D. Conner and continued to operate The Flower Shop for 36 years, until it closed on October 31, 2013.
167 N. Loudoun Street (Murphy Beverage Company)
By 1885, Sanborn maps labeled the structure as a two-story grocery, and by the 1890s, it housed J.P. Kremer & Co., a local dry goods store. By 1897, the space was likely home to a clothing business—possibly the New York Clothing House, later confirmed to be operated by the Feinberg Brothers. Financial troubles forced them out after a five-year stint.In 1903, the building was repurposed again, this time as a bank, only to sit vacant by 1912, following a major flood in 1906 that impacted much of downtown.
147 N. Loudoun Street (T.T. Wall's)
By 1885, the building housed a business labeled as "Fancy Notions", which continued through at least 1891, according to Sanborn maps. In 1897, the shop evolved into "Stationery, Books, and Queens", and by 1903, T.T. Wall Stationery had taken over, establishing a long tradition of books and paper goods at this address.The upper floors were often used as residences, with records showing Mrs. Lucy Kinzel (wife of Henry Kinzel) and their children living at 149 N. Loudoun in the early 20th century, the property having been deeded to Henry Kinzel on May 10, 1865.
125 S. Loudoun Street (Moon Phased)
Architecturally, the building still reflects its early Federal-era character, including the three-course brick cornice, wood sills, and dentiled lintels with rosetted corner blocks. According to city records, the arched fanlights above the twin entrance doors are likely original to the structure.Originally a dwelling, deed records show the property changed hands at least four times between 1868-1908. In 1914, Confederate veteran Thomas L. House, then in his 70s, purchased the property. A grocer by trade, House operated a store here until roughly 1922, when the business and the building passed into new hands. T.L. House, a member of the Turner Ashby Confederate Veterans Camp, spent his final years at the R.E. Lee Camp Home in Richmond before being laid to rest in Hollywood Cemetery.
19 W. Cork Street (The Discovery Museum)
The earliest documented ownership begins with George W. Anderson, who deeded the property to James W. Anderson in 1870. Throughout the late 19th and early 20th centuries, Rhoda C. Anderson—widow of James—occupied the log cabin home. In time, modifications such as brick was added to the exterior and was noted as a brick residence with other outbuildings on “Cork Street and Stable Alley” (the old name for Indian Alley).The home bore witness to a few dramatic moments, including the 1916 death of Julia Bahlman in the home, and a 1917 stabbing incident involving Rhoda’s grandson. Rhoda herself passed away there in 1940, and in 1941, the house was sold at auction following her death.
12 S. Braddock Street (SOJO)
1924: Huntsberry’s Sign Works operated at 12 S. Braddock, offering banners and show cards—some delivered within 15 hours.1927: Charles A. Pine briefly sold used cars here before moving his dealership farther down Braddock.
103 N. Loudoun Street (Village Square Café)
Though the building at 103 North Loudoun Street dates back to the early 1800s, its long-standing history as a commercial fixture began with Miller’s Drug Store. Relocating to the Loudoun Street location in 1806, the Miller family operated what would become the oldest family-run drugstore in the United States, originally founded in 1764. Miller’s stood not only as a source for pharmaceutical care, but also as a trusted gathering spot for generations of Winchester residents.Through the 19th century, the storefront shared the block with neighboring businesses such as Rosenmeyer’s (hats and shoes), Virginia Loan & Thrift Corp, Dr. Godfrey L. Miller, N. Main Dentist, and N. Main Boots and Shoes.
29 E. Boscawen St. (DFC-LMA Architects)
By 1898, the property was already serving a commercial role under Ms. Lee Winkley, one of the early documented proprietors of the address. Though records are limited, her presence marks the beginning of the building's shift from private residence to downtown storefront.
121-129 N. Loudoun Street (Taylor Hotel)
Captain Edward McGuire, an Irish immigrant, established a log tavern on this site around 1755, fronting what is now Loudoun Street. It was part of Winchester’s early layout on Lot 61 and played a role in early transportation and hospitality for the Valley. The tavern—complete with stables across Braddock Street—catered to travelers along the Great Wagon Road and later the Valley Turnpike. By 1782, McGuire had become influential enough to lobby for changes to local liquor laws, giving large tavern owners like himself more control.After McGuire’s death in 1806, his grandson ran the inn until it was sold in 1830 to Bushrod Taylor, a farmer from Berryville. Taylor rebuilt after a fire in 1846 and completed a handsome three-story brick hotel with colonnaded porches and rear wings by 1847.
31 E. Piccadilly Street (Paladin Downtown)
The address first appears on the 1885 Sanborn Maps as Jones Creamery, run by Mr. J.F. Jones, a name that pops up frequently in the Winchester Evening Star for his local generosity. Known for crafting special Easter and Christmas ice cream flavors, Jones even operated an ice cream wagon, bringing much-needed refreshment to church socials and town picnics before air conditioning was a thing.
