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The Most Photographed Street in Boston

Acorn Street is Boston’s most photographed street. This famous cobblestoned street in the Beacon Hill neighborhood was laid out in the 1820s. Originally called Kitchen Street because the small row houses were once occupied by the cooks and coachmen who lived close to their employers. Some homes were even used as horse stables at one time!

Over the years, Acorn Street has become one of Boston’s popular tourist destinations. Its 19th-century charm,  colorful flowers in the window boxes, antique gas lamps along the narrow brick sidewalks all add to its character. And then there’s the eye-catching historical treasure: the cobblestones.

So, what’s the backstory on Boston’s most iconic street? In the early days, the ground was filled with rounded, irregular shaped stones, known as “cobs”. As Boston developed from a town into a city, flat land was needed for the housing boom. Developers extracted the cobs from the soil, which resulted in piles of cobblestones. Consequently, the stones were repurposed into creating the rocky path sloping down the middle of Acorn Street.

Acorn Street is a private way in the now affluent section of Beacon Hill. Residents are responsible for their maintenance and upkeep. They formed the Acorn Street Association in the 1980s to prevent the city from paving over the cobblestones. Today, the nine quaint brick row houses are about 2000-3000sq.ft with assessed values range from $1 million+ to $6 million.

The best time to take pictures of Acorn Street is early in the morning, late afternoon, or anytime on a cloudy day—definitely not when the sun is shining and shadows zigzag up and down the street. The brick sidewalks and cobblestones are especially shiny and vibrant after a rainstorm. In its unintended way, Acorn Street challenges photographers to revisit and discover new and interesting ways to capture its allure.

(Acorn Street is one of the stops on the 90-minute Beacon Hill tour and the 2-hour PhotoWalks Highlights of Boston tour.)