- The Boston Harbor Islands played an important strategic role during the Revolutionary War.
- Used by farmers since 1634, Peddocks Island's proximity to the mainland ensured a prominent military role for the island. Said to be the site of a patriot infantrymen's raid on a Loyalist farm, Peddocks also saw over 600 patriot militiamen stationed on the island in 1776 to guard the harbor against the return of British troops.
- Grape Island never hosted any military fortifications, though in 1775 it was a site of a skirmish over hay during the Revolutionary War. This skirmish is known as the Battle of Grape Island.
- Boston Light, located on Little Brewster, was largely destroyed by the British when they evacuated Boston at the close of the Revolutionary War, but was rebuilt in 1783.