where it all started

 ASHLAND BARBERS FORMALLY DRAKE BARBERSHOP EST. 1902
Cross North Broadway and continue on West Short while taking notice of the 180-year-old building at 309 West Short (on your left before North Mill). This is Lexington’s oldest surviving post office (ca. 1830). The building to its west at 311 is a remnant of the 19th century REED-DRAKE HOTEL.On your right at 300 West Short (on the southwest corner of West Short and N. Mill Street) is a building that began as a pharmacy in 1905. It became Sageser Pharmacy from 1930 to around 1970, after which the building was renovated and converted to law offices. Continue to Cheapside Park, on your right at the southeast corner of West Short and Cheapside (Stop 9). South Ashland Avenue HOME OF ASHLAND BARBER SHOP Continue east for another block on East High Street to the South Ashland intersection. Turn left on South Ashland (Stop 26). You have entered the South Ashland Historic District, which is included the Woodlands National Register Historic District. Its houses were built in the late nineteenth and early twentieth century. A variety of architectural styles of the period are represented with many of the structures reflecting combinations of styles. Included in this district is Woodland Park, which was designed by the Olmstead Brothers landscape architecture firm.
Continue on South Ashland until you reach Fincastle Road on the right, a block before you reach East Main Street at the stoplight. (Skip to Stop 29 if you desire to eliminate 2 miles from your tour.) Turn right on Fincastle Road and continue 5 blocks through the old and peaceful Ashland Park neighborhood until you reach Sycamore. This neighborhood is part of the National Park Service’s Ashland Park Historic District. As you bike through the Ashland Park Neighborhood, you will notice that it is one of the most unified and aesthetically pleasing neighborhoods in Lexington. Colonial Georgian, Federal, Queen Anne Victorian, Colonial Revival, Dutch Colonial Revival, Tudor Revival and Craftsman are among the architectural styles found in the area, giving the visitor a rich survey of our American architectural history. In 1904, the Clay family hired the Olmsted brothers to create plans for a residential neighborhood on the 600-acre estate. Constructed over a 15-year period, the development was completed around 1930. A short distance past Sycamore on the left is Henry Clay’s Estate, Ashland.
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