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Alleys. Some people love them. Some people hate them.

Perhaps the last alley developed in Winchester is located behind duplexes on April Way, a paved pathway to access rear garages.

Cities probably don’t like alleys because they add to the street maintenance requirements of local government.

Law enforcement probably doesn’t like them because they may provide locales for illegal activity.

Developers don’t like them because they use up land that is more valuable if developed for the houses themselves and because there is frequently the question of whether the maintenance of the alley is the responsibility of the property owner or the municipality.

If one looks at a Google Earth image of Winchester, it quickly becomes apparent that alleys are confined to the neighborhoods that closely border the downtown area, neighborhoods that were developed mostly at the beginning of the 20th century.

A recent conversation with local historian Harry Enoch shed some light on the evolution of alleys.

The conversation with Enoch resulted in the conclusion — perhaps questionable — that alleys were developed as part of the early growth of Winchester because of the way houses were designed and built. And the Sanborn map of 1890 would seem to bear out this hypothesis.

That map, which illustrates alleys separating most of the blocks surrounding the downtown area, shows numerous outbuildings adjacent to those alleys and, obviously, a part of the building lot facing an adjoining street.

In those days, before the abundance of the automobile, people were undoubtedly getting about using carriages and, more rarely, the few mechanical vehicles available at the time. 

Houses were not designed with attached garages, and outbuildings served that function, separated from the main house and accessible only from the alley (except by foot, of course).

It’s possible to walk many of the alleys today and still find a large number of these outbuildings in use.

In days gone by it was common to find youngsters in the alleys because they were more likely to be unseen by adults — and not necessarily up to mischief. 

They were often shortcuts to other areas, and they offered different scenery from that found along the streets.

Also, in the past, it was not uncommon for alleys to be unpaved, often with surfaces only of stone or very sparsely paved. Even today, a good number of the alleys, especially those within residential areas, are only lightly paved.

There is a certain charm about alleys. They are almost always safe, especially during daylight since they seldom have traffic on them, and they provide good walking pathways as well as the opportunity to see what is happening in the rear of buildings, not for purposes of being nosy but just to see the “other side” of what one normally sees when walking or driving the city streets.

These views also provide one with a glimpse of how things developed early on, mostly because the buildings still existing on the alleys have not gotten the attention given to the main residence or place of business.

There is a wealth of interest in alleys that lies just beyond what everyone so normally sees by restricting their travels to the streets.