39. Shepherd District Free School

SE Corner of New and Princess Sts. One of the two public schoolhouses in town built by the state of Virginia in 1848, it continues to serve the cause of education as office space for Shepherd University professors. It is believed to be the oldest free schoolhouse in West Virginia.


40. Tolliver's Hotel and Ice Cream Parlor

SE corner of Princess and German Sts. Owner J. Matt Tolliver seems to have been the downtown area’s first successful black businessman. His name appears in the town records during the years 1877 to 1908. After his popular restaurant burned in 1894, he built this brick building, where he ran a hotel and ice cream parlor. From 1899 to 1909 the town granted him an annual hotel license.

41. Hodges Building

SW corner Princess and E German Sts. A large brick structure and residence from the early 1800s to the 1880s. Resident families included three generations of the Reinhart family, then the Line family. From 1854 until his death in 1858, it was the home of the Honorable Henry Bedinger, the first U.S. Ambassador to Denmark. In the 1880s, G.T. Hodges established a large general store in the front corner room. The old entrance is still visible from the Princess Street side.

42. Yellow Brick Bank

NE corner of German and Princess Sts. In 1906 Jefferson Security Bank removed an older brick building from this site and erected the current structure, a modified Beaux Arts style building. When the bank moved in 1975, new owners converted the old bank into a restaurant.


43. Gray Lodge

203 E German St, adjacent to the Yellow Brick Bank. A complex of three structures built for the Shepherd family as a town home, including a small rectangular brick building (which served as a doctor’s office from c. 1850 to 1890), a carriage house (converted into a tea room and tourist inn c.1920), and a Greek Revival brick house with iron grill work on the front said to have been brought from New Orleans by a member of the Shepherd family. Author Willa Cather spent a summer at the Gray Lodge working on a novel.

44. Wynkoop's Tavern

204 E German St, opposite the Gray Lodge. A log cabin owned by Martin Entler housed a tavern on this site as early as 1769. In 1781 Cornelius Wynkoop acquired the tavern. Here, some alleged, steamboat builder John Fitch stayed while spying on James Rumsey’s experiments. Wynkoop erected the present brick structure c.1791. During the early 19th century it became a fashionable stopover place for visitors. Six generations of one family—with different surnames—occupied the house from 1800 to 1986. Among them were Selby, Hamtramck, and Billmyer. Notable among the residents was Col. John Francis Hamtramck, a West Point graduate who commanded a volunteer regiment in the Mexican War, helped train local militia units in the antebellum era, and served as town mayor.


45. Reynolds House

207 E German St. Built in 1865 by Dr. John Reynolds who served the town as a doctor for more than 40 years. As town mayor 1860 to 1862 he had to deal with a dangerous situation when unknown persons on the Shepherdstown side fired at Union pickets across the river, drawing a protest and threat from authorities on the Union side. Reynolds’ wife Katherine led a community fundraising drive for the town hall attached to McMurran Hall in 1889. The building was later named in her memory.

46. Poorhouse

213 E German St. Town records list the poorhouse as early as 1805. Here, following Elizabethan tradition, the town provided a modicum of care for the poor and elderly. Though it began as a log house, it has been enlarged and covered with wooden siding. Iron rings in the attic rafters suggest that some of the residents may have been restrained.

47. Parran House

301 E German St. In 1796, this brick house replaced an earlier log house. The trials of the Parran family poignantly illustrate the tragic impact of the Civil War. Dr. Richard Parran, a physician, died in 1851 leaving his widow and five daughters. The widow Parran remarried on the eve of the Civil War, but her husband joined the Confederate Army and was killed early in the war. One of her daughters, Lily, married William “Willie” Fitzhugh Lee, a cousin of Confederate General Robert E. Lee. Willy died as a result of wounds at the First Battle of Bull Run. Another daughter married Dr. William Tinsley, also in the Confederate service, who helped organize the town’s care for the wounded after Antietam. Lily Lee and her husband had known Confederate General Jeb Stuart and his wife in happier times. Stuart visited Lily at the Parran House during the War. Eyewitness accounts of Stuart’s deathbed will in May, 1864, differ, but one version reports that Stuart ordered that his golden spurs be given to Lily Lee. There are reasons to doubt that Lily ever received them.

48. Train Station

Between E German and E High Sts., on Audrey Egle Dr. The Norfolk and Western Railroad built the passenger station in 1909. Waiting rooms and rest rooms were segregated. After nearly a half century of service, passenger traffic ended in 1957 and the station closed, to be used by the railroad for storage. In 1996 the railroad deeded the passenger station to the town for $1.00, and the building was restored and redesigned as a multiple use facility.