Victorian novelist Henry James and 1990’s TV lawyer Ally McBeal felt equally at home on Beacon Hill, which rises steeply on the north side of Boston Common. This is the neighborhood that springs to most people’s minds when they think “Boston”: gas streetlamps lit 24 hours a day and cobblestone alleyways lined with brick Federal-style townhouses that are home to some of Boston’s richest residents.

The most exclusive address on the hill is Louisburg Square, where wrought-iron railings surround a park of beech and alder trees, and wealthy Bostonians including Senator (and 2004 presidential contender) John Kerry make their homes. A block south of the square, go ahead and snap a shot of the picturesque cobblestone alley of Acorn Street, supposedly the most photographed street in the world.

At the bottom of the hill on the east is commercial Charles Street, where doyennes with small dogs shop in a profusion of antiques stores, and young lawyers in the mold of Ally take their laptops to cafés on weekends.