
This week for Georgetown Time Machine, GM is visiting upper Wisconsin Ave. The photo comes from the DDOT archives.
GM believes the photo is from the 1960s, based upon the cars and the fact that there are no streetcar tracks down the center of the road (the streetcars stopped in 1962).
To get your bearings, the large building up the hill in the center of the shot is now the British School. That is just about the only building on the east side of the street that is still standing today.
The most notable building in the photo is the Safeway at the center:

This was the first Safeway building at this location. It was built in 1955:

Despite being built during the height of suburbanization, the store was built right up to the street. To be sure, it was still surrounded by a large parking lot, but there was somewhat of a consistent streetscape. Interestingly, before its construction, this stretch of Wisconsin Ave. was just parking lots:
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