How to Explore Boston's North End Like a Local

If that sounds extreme, it's only because the city’s oldest residential neighborhood matters that much to its residents, and to the city at large. The labyrinthine, lilliputian North End (square mileage: 0.36), first settled in the mid-1600s, today embodies Boston’s IG-worthy charms, from its cobblestoned streets to its European-inspired brick townhouses. North End’s history is the stuff of Greater Boston’s lore: the Anti-Stamp Riot, the Great Molasses Flood, Sacco and Vanzetti’s wake.

The North End became an Italian-American enclave starting in the mid-1800s, reflecting the larger wave of Italian immigrants sailing to the US. Settlers from Genoa arrived first, and many made their living hawking fruits and vegetables as well as homeland imports such as wine, cheese, and olive oil.