1. Beacon Hill
Brick sidewalks, gas lanterns, narrow streets, and Federal-era rowhouses with purple windowpanes. Beacon Hill is what most people picture when they think of old Boston. The neighborhood sits on a steep slope between Boston Common and the Charles River, and walking its streets feels like stepping into the 19th century. Acorn Street, a cobblestone alley barely wide enough for a car, is the most photographed street in the city. This is where Boston's political and literary elite lived. Louisa May Alcott, Oliver Wendell Holmes, and several Massachusetts governors called these blocks home. The Boston Athenaeum, one of the country's oldest independent libraries, is at 10 1/2 Beacon Street at the neighborhood's edge. Charles Street, running along the base of the hill, has antique shops, small restaurants, and cafes that feel untouched by chain culture. Beacon Hill is free to wander and open around the clock. It's directly uphill from Boston Common and a short walk from the Freedom Trail. Wear comfortable shoes. The brick sidewalks are uneven and the hills are real.