Boston is where the American Revolution started, and it hasn't stopped talking about it. The Freedom Trail is a 2.5-mile walk past 16 sites, from the oldest city park in the country to a granite obelisk in Charlestown. Along the way are the graves of men who signed the Declaration of Independence, the steeple where two lanterns were hung in April 1775, and a wooden frigate from 1797 that is still afloat. The city is also home to Harvard (1636) and MIT, so the 18th century and the research labs are a subway ride apart.
It's a small city by American standards. You can walk from the State House to the North End in 20 minutes, so five days feels comfortable rather than rushed. It is also old and crooked: the streets follow cow paths, the brick sidewalks are uneven, and late-fall weather can turn from golden to gray rain in an afternoon. The food is better than its reputation. This is a port town, and the lobster rolls, oysters and chowder are the reason to come hungry.
Each day gets one part of the city. Day one is the Common, Beacon Hill and the first half of the Freedom Trail, day two the North End and Charlestown, day three Fenway and Back Bay with the two big art museums, day four Cambridge, Harvard and MIT. Day five is Salem. We picked it over Lexington and Concord because the train from North Station takes about 30 minutes and needs no car, and the witch trials and its maritime museum are a different story from the one you've heard all week. The honest catch is October: Salem turns into a Halloween theme park for the whole month, and weekends are packed. Go on a weekday. Lexington and Concord, where the shooting started, are the better swap for anyone who wants more Revolution, and they sit in More Time with Cape Cod and Plymouth. Start on a Thursday: the Gardner and the MFA are closed Tuesdays, the Harvard Art Museums and the Bunker Hill Museum on Mondays (Bunker Hill on Tuesdays too), and the Peabody Essex Museum in Salem on Tuesdays and Wednesdays, and this order keeps all of them open and puts Salem on a quiet Monday. For the wider picture, see the United States country page.