All these are courtesy of the BRA's
Digital Atlas. I encourage everyone to rummage around the site, as I'm sure there's plenty more gems to be found.
This first set is from December 1, 1955, starting with the overview image. You can see how the flash client "layers" whatever images you want it to. To the left is a 2001 aerial, to the right dates from 1969 (those are later in this post). You can toggle back and forth at will.
1.
2. Harvard Square
3. Northern Harvard
4. East Cambridge railyards, future site of Northpoint.
5. East Cambridge
6. Kendall Square
7. MIT Central
8. MIT West.. what are those barracks looking structures?
9. Copley Square
10. Future Prudential Center site
11. West Fenway
12. Northeastern
13. Longwood
14. Kenmore Square
15. BU Central
16. BU West... two years after the Braves left town
17. Finally, the old West End
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This other set dates to April 9th, 1969. As you'll notice, coverage differs between the images. For instance, this one shows the Seaport area, but not Longwood or Harvard.
18. Downtown
19. My, oh my.
20. Seaport
21. Back Bay/Copley/South End
22. Fenway/Kenmore
23. Fenway/Northeastern
24. East Cambridge
25. Kendall/MIT
This image has a higher resolution than the 1955 one, so now we'll zoom in, focusing on visible construction projects.
26. Construction sites include 100 Federal and 99 High
27. Arch St. garage and the Five Cents Savings Bank, aka Borders
28. State Street environs
29. Center Plaza and One Boston Place
30. Northern Government Center
31. Yep
32. Mass General
33. South Station. Note how much more of it used to exist
34. Tufts/New England Medical Center ripping apart Chinatown
35. Midtown
36. John Hancock being excavated, and the BPL prepping for the Johnson building
37. Future home of Copley Place
38. 101 Huntington in its infancy
39. Christian Science Center
40. Last one, Kendall Square and the Volpe