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  • Maddie Lamothe

The Best Walks in Boston

Boston is obviously one of the most beautiful cities in New England. Notoriously, our streets aren't the easiest to navigate in the car. Plus, when you walk through a city's streets, it's the most immersive way to experience it. But where to start in a place that has so many streets to choose from?


  1. Charles River Esplanade- The Charles River runs from the West End to Back Bay, two iconic neighborhoods of Boston. With views of the rowers and sailboats, to the city skyline, this is a great way to feel a part of nature while still in the city. You can even rent a kayak of your own if you feel like adventuring!

  2. Freedom Trail- We would of course be remiss to not mention our favorite walking tour of Boston. From the willow trees hanging over Boston Common, to historical brick buildings, to walking along the water, you will get a true well-rounded experience of Boston in less than a day.

  3. North End - A foodie's dream, traipse through the beautiful North End for unbelievable Italian food and famous cannolis. The narrow streets are packed with happy people walking through and enjoying the views. Right by the West End, you'll find it worth stopping off if you're in the neighborhood.

  4. Acorn Street- The most photographed spot in the city, come here if you want a photo along the narrow cobblestone walkways between mossy brick buildings. It's a treat for those who appreciate architecture, or anyone looking to spiff up their Instagram grid.

  5. Boston Common- Where the Freedom Trail tour starts! With us, you'll get to learn a bit about the history of this park that boasts a great location, a frog pond, historic statues, and more. A great place for a quick stroll, a picnic, or depending on the time of year, some seriously lush flower gardens.


While there are many other neighborhoods worthy of your visit, this is a great start to your Boston adventure. Happy trails!

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