Downtown Winchester has over 100 historic structures and a remarkable collection of late 19th-century architecture. However, on one side Main Street buildings are raised above the level of the street by as much as six feet, limiting access for people of all abilities.
As part of the Master Plan, an open space analysis identified an absence of naturalized areas or parks in the downtown core, concentrations of heat island effects and substantial areas of impervious surfaces. Reconfiguring the nearly 300 feet of continuous stairs along Main Street improved access for those with disabilities, provided much-needed outdoor terrace spaces for restaurants and increased tree coverage.
The Downtown Main Street is advancing planning for the infrastructure improvements along the corridor in tandem with a downtown investment fund and façade improvement program.
- CityVisions Associates
Main Street Winchester


High Street Park
Opposite the County Courthouse, this new public space reduces impervious surfaces, increases tree canopy, substantially increases space for outdoor seating and dining and overcomes barriers to mobility.