In my opinion, if improvements within the roadway restore a sense of pedestrian and bicyclist comfort, which was very common pre-WW2 then it's entirely in keeping with a pre-war era historic district. For a post WW2 development, then sidewalks were less common, which would could add a level of complexity to installing pedestrian friendly pathways. We do have one residential historic district in town where the lack of sidewalks is considered a character defining feature. Thankfully WW2 development also came with culdesacs, so that district isn't a major thoroughfare for peds.In our downtown historic district, established in 1979, an entire block-length of street was shut down and turned into a pedestrian promenade (in 1982). The Square went through a redesign a few years ago. When we reviewed the proposed changes, our main concern was visibility of the historic structures, that historic artifacts within the scope of the project be preserved (which meant some historic sidewalk on one corner), and that historic district signs be reinstalled if they were removed during construction.
We have a large national residential historic district that had a new bikeway installed a few years back. This included changing some parking, installing a roundabout at one intersection, and restriping so that there were bike lanes with buffer space on either side of the bike lane. We reviewed these changes with an eye towards what affect they would have upon intersections in particular. There pedestrian improvements might affect historic shale sidewalks. (Turns out most had been removed decades before.)In general, anything that gets people out of their cars and onto the streets by bike or on foot, gets them seeing the historic buildings that before they were just whizzing past. I'm all for such street improvements. Given that we add painted pianos, painted transformer boxes, and painted planters to our historic downtown (and pavers where there used to be dirt roads) and they help to enliven the area and strengthen the public's bond to the area, I think such things are fine. And they're all removable, I would put painted streets in that same category. They can enliven the area. And depending on how many cars are traveling over them, the paint really won't last long. Even if it's regularly repainted, it's temporary given that streets get repaved or at least chip-sealed fairly regularly. Unless the asphalt (or cement) street is a character defining feature, I'd say bring it! Get people out there walking and biking and appreciating what they were previously just flying past. :-D
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