North End Boston: Italian Food, Cannoli & the City's Oldest Neighbourhood

The North End is Boston's oldest neighbourhood and its most delicious. A small peninsula north of Downtown Crossing, separated from the rest of the city by the Rose Kennedy Greenway, it was settled in the 17th century and remains the most densely populated and most Italian neighbourhood in the city — a product of the massive Southern Italian immigration of the late 19th and early 20th centuries that never quite dispersed the way similar communities did in other cities.

The neighbourhood's central street is Hanover Street: a dense strip of Italian restaurants, pastry shops, and cafes that operates at high energy seven days a week, especially on summer evenings and during the neighbourhood's street festival season (the Fisherman's Feast and Saint Anthony's Feast run through July and August with processions, outdoor food vendors, and considerable noise). The side streets off Hanover contain smaller, older restaurants that are generally better than the main drag options.

The cannoli question: Mike's Pastry and Modern Pastry are the two North End institutions, located 100 metres apart on Hanover Street, and the debate between their loyalists has the fervour of a theological dispute. Both are genuinely good; the line at Mike's is longer but moves quickly. The ricotta filling, the shell crispness, and the chocolate chip placement are all seriously debated. A side-by-side comparison is the correct approach.

Beyond pastry: Neptune Oyster on Salem Street is one of Boston's best seafood restaurants (no reservations; arrive early or expect a wait). Giacomo's on Hanover is a tiny room serving reliably good pasta without reservations. The Paul Revere House on North Square is the oldest remaining structure in Boston (1680) and a worthwhile stop between meals.