It doesn't make any sense on first glance.
On further inspection, you might notice that most of the lines are aligned with present-day roads on the gray GoogleMap.
How about this version?
I made this map piece by piece, using Google's MyMaps to draw lines and add icons from historical maps. Some I found at http://www.newtonma.gov/gov/it/gis/historic_maps.asp, but I also benefited greatly from local historical society staff, who gave access to physical copies. I also added details from an 1831 document and an 1848 map to get this:
Now see all the layers together, including the fragmented picture at the very top from the 1855 map:
In just 7 years, there has been so much growth in the northeast neighborhood that the icons crowd together.
In just 7 years, dozens of public roads have been extended or created to accommodate new business and settlements.
In the same period, Newton's population swells by about 2000 new residents, and by the same number again in the following decade.
Now I'm left with the question: how best to show this to my students? Explain it in a video? Let them explore the layers of the GoogleMap independently? As some sort of scavenger hunt? None of the above??