July 30, 2015, photo by Shawn Patrick Ouellette/Staff Photographer; April 8, 1969, Portland Evening Express photograph courtesy of Portland Portland Library Special Collections & Archives

The black and white photograph above, which ran in the April 8, 1969, Portland Evening Express, shows heavy machinery demolishing Old Port buildings along Middle Street in order to clear a path for the new Franklin Street Arterial.

The finished result – visible in the 2015 photo – has been the subject of a years-long planning study, recently adopted into the City of Portland’s Comprehensive Plan, to make the street smaller, safer and more accessible to foot traffic.

The Portland Room of the Portland Public Library is in the process of organizing and conserving the archival collection of original Portland Press Herald, Maine Sunday Telegram and Evening Express photographic negatives — a major collection that spans from 1937 to 2005. Find more photos at www.pressherald.com/flashback/.