The High Street, Hailes and Gloucester Street presently form the spine of this ancient town that can justly claim a thousand years of continuous occupation. At first sight Gloucester Street seems rather spartan and stark. It is a long curve of ancient cottages welded by time into a tight terrace of stone homes. Grapevines grow over the silvery gold walls.
Stable doors are something of a tradition here.
The frontages may seem quite bland, but each cottage holds secrets. Gothic doorways, massive timbers, gruesome gargoyles and mysterious carvings hide behind lace curtains. Inside, one may find cavernous Tudor fireplaces reappearing after long concealment. Newly rediscovered wells are sometimes revealed, and long lost wall paintings have been uncovered. There are still many more Winchcombe secrets to be found.