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Boston, Massachusetts
The root: The Revolution's hometown — the Tea Party, Paul Revere's ride — and a city of American firsts that never stops arguing.
Eat: Union Oyster House — America's oldest restaurant, serving since 1826. Mike's Pastry — the North End cannoli pilgrimage. Legal Sea Foods — the city's classic clam chowder.
Skip — don't: The Faneuil Hall food-court chains dressed up as "historic dining" — Quincy Market's real gems are the pushcart originals.
Specialty: Clam chowder, baked beans, and the cannoli wars — plus a sports town that takes it all personally.
Shops & crafts: Faneuil Hall Marketplace — local crafts among the crowds. Newbury Street — boutiques and bookshops in brownstones. The North End — Italian groceries, espresso, and pastry boxes to carry home.
See: Freedom Trail — walk 2.5 miles of Revolution history. Faneuil Hall — where America has argued since 1742. The North End — Italian streets on the harbor, cannoli in hand.
Main Street: Tremont Street — past the Common, the Granary burying ground, and King's Chapel, history on every block.
After dark: The Boston Pops at Symphony Hall, or a comedy club in the Theater District — Boston laughs at itself best.
When — events
Boston Marathon — Patriots' Day, the third Monday in April. Boston Pops Fireworks Spectacular — July 4 on the Charles.
Event dates are the typical annual timing; confirm with the town before traveling.