Building Blocks of Boston; downtown walking tour

Discover Boston's modern sites & behold historic delights on your guide's Ultra HD scroll! See, hear, and feel how the city was built over 400 years.
Join a captivating 2-hour guided walking tour covering 1.3 miles (2 kilometers) through the heart of America’s most groundbreaking city. Starting at the Boston Common Visitors Center, you’ll embark on your journey by learning why 700 pioneers left Old England on an incredible 2 month long sailing voyage to establish Boston.


Our first stop is the Soldiers and Sailors Monument, perched on the highest hill in the Common! Here, your guide will show Boston’s original landscape and dramatic photographs showcasing the massive landfill projects that doubled the city’s size. As we walk to exit the Common, you’ll uncover the inspiration behind the Embrace sculpture, a tribute to Dr. Martin Luther King Jr.


Entering Downtown Crossing, Boston’s premier shopping district, you’ll experience the fusion of old and new in this vibrant neighborhood. Depending on your group’s interests, your guide will delve into the history of photography, the writings of prominent Bostonians, or the downtown buildings once home to Harvard University and MIT—fun fact, they were neighbors in downtown Boston before they were in Cambridge!


Midway through the tour, we’ll pause for a ~10-minute break at Winthrop Square. This newly constructed public space has ample seating to rest your feet and pristine restrooms. This hidden gem, possibly Boston’s most photogenic spot, is perfect for capturing photos to share with friends and family.


Refreshed, we’ll walk to South Station, which once housed the world’s largest covered train yard. You’ll witness Boston’s remarkable transformation from railway to expressway to greenway, illustrated with stunning colorized photos of the waterfront. This area is a showcase of architectural beauty, where old and new buildings blend through “facadism,” a breathtaking building practice which has been perfected in Boston.


As we leave the station, you’ll hear the iconic song that inspired the name of Boston’s subway pass, “The Charlie Card.”


Your guided walking tour continues to Post Office Square, where you’ll admire the charming parks and architecture of the Financial District while hearing heartwarming love stories. We conclude our journey at the Old State House, reflecting on Boston’s incredible achievements. To leave you inspired, your guide will share an incredible letter from a 1901 time capsule, offering a glimpse into the hopes and dreams of Bostonians for the future.

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