This wonderful collection of maps provides access to hundreds of maps of Boston dating from 1630. As they are listed in chronological order it is easy to scroll to a desired period. The website also provides numerous ways to filter to locate more specific maps.
A number of interesting historic maps of Massachusetts and Boston from the Massachusetts Historical Society.
Mapping Boston by Alex Krieger, David A. Cobb, Amy Turner, David C Bosse (Cambridge, Mass.: MIT Press) O'Neill Library Oversize Book Area (GA430 .M36 1999)
"The book includes both historical maps of the city and maps showing the gradual emergence of the New England region from the imaginations of explorers to a form that we would recognize today. Each map is accompanied by a full description and by a short essay offering an insight into its context...A highlight of the book is a series of new maps detailing Boston's growth."
Explore a Google Map interface, limiting by date ranges, and then link out to appropriate digitized historical maps from the various partner collections (including the British Library, the New York Public Library, and others).