With our recent and upcoming expansion to Boston and Philadelphia respectively, one question for the ages has continually plagued us here at Stray Boots headquarters. Which old cobblestone street is the cutest: Acorn Street in Boston or Elfreth’s Alley in Philadelphia? As a New Yorker, born and raised, I’m tempted to throw in Barrow St. or some other windy Greenwich Village, Harlem, or Brooklyn side street in the mix, but alas, I know that no street in the Big Apple holds a candle to either. I imagine the same is true of many a historic town.  So for the time being, let’s take a look at these two amazingly adorable back alleys and see if we can’t crown ourselves a winner

History: Winner:  Elfreth’s Alley
As the oldest continually residential block in the U.S., Philly’s Elfreth’s Alley is tough to match. It dates back to 1702, just twenty years after William Penn declared the city Pennsylvania’s capital. Many of the houses on the street date back to the 18th Century, and still bear seals of various fire companies, dating back to when fire departments were private enterprises, not municipal services. There’s even a small museum tucked into the alley, where you can step back in time and learn about the street’s rich cultural history amid an ever-developing city and nation.

Formerly home to 19th Century artisans and tradesmen, the 19th Century brick houses that line Acorn St. are certainly historically impressive in their own right. It’s easy to see why for centuries Boston’s most influential figures have chosen Beacon Hill as their home. Nevertheless, Elfreth’s Alley has far more candles on its cake, which in this contest is all that counts.

Aesthetics: Winner: Acorn St.
Elfreth’s Alley is totally adorable. You just want to hug its tiny back alley Bladen’s Court, equipped with an old red water pump and all. Residents take pride in maintaining the appearance of their homes, and it’s definitely got loads of charm.

But Acorn St. is absolutely jaw-droppingly beautiful. The sort of quiet oasis where the only sounds are the pleasant chirping of birds and the only smells the fragrance of flowers, Acorn St. feels entirely make-believe, especially when you stumble on it between the winding pathways that make Beacon Hill so fun to explore. That it’s Boston’s most photographed street isn’t hard to believe, despite all the other amazingly picturesque blocks of mansions, gardens, and historic landmarks throughout the City. Thus, Acorn wins the beauty pageant.

Welcomeliness: Winner: Elfreth’s Alley
Part of being cute is being approachable. An adorable kitten that scratches your eyes out becomes a little less appealing.  So, while you won’t feel unwelcome along the cobblestones and architecture of either street, there’s a distinct difference in how they treat you as a guest. While Acorn St. is plenty enjoyable to look at and wander down its cozy slope, there are no invitations to welcome you in and learn more about the folks who have lived here over the years.

Elfreth’s Alley on the contrary does just the opposite. In addition to the little museum, where you can learn about the alley’s history, many residents have chosen to put little sheets of paper in their windows retelling the stories of their houses and those of the people who lived there. Even better, on Fete Day, this year on June 3-4, residents of the alley open their homes to the public. I know I wouldn’t want to do that with my apartment.

It’s that warmth in sharing their homes and their history that makes Elfreth’s Alley so appealing. Perhaps a natural fit for the City of Brotherly Love, it’s still not so common for the high-rent-paying occupants of National Historic Landmarks elsewhere to welcome visitors with such open arms. And that they do gives an added charm to the already cute-as-hell Elfreth’s Alley

WINNER: Elfreth’s Alley
Like a well-fought game of rocks-paper-scissors, Elfreth’s Alley takes it with 2 out of 3.