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Boston’s Big Dig Walking Tour

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  • Explore the ′Big Dig′ with an architectural expert
  • Find out Boston has been transformed over centuries
  • Get fascinating insights into Boston′ history
  • See things that other visitors miss
  • Small group tour with plenty of personal attention


Delve into Boston’s rich built heritage with the help of a specialist architectural historian on a captivating tour.

In the 1990s work began on what at the time was – and still is – one of the most ambitious urban engineering projects in history: the burying of Boston's highway system to free its historic center from traffic, shadows, and unsightliness. Dubbed the "Big Dig" and lasting nearly 20 years, this mammoth project recast downtown Boston, returning its historical streets to the sun and transforming a curving swath of land into one of the best urban parks in the country. During this 3-hour walking tour your guide will use the Big Dig as a lens to look deeper into the history of the city and trace its evolution from the 17th century to the present.

This is very much a "built environment" walk, in which you will look at buildings, streets, and the fabric of the city in order to "read" Boston's history, often hidden in overlooked details.

This is small group tour so you will have plenty of chance to interact with your expert guide.


To join the Boston’s Big Dig Walking Tour, you should make your way to Bruegger's Bagel Bakery at 7 School Street, located at the corner of School and Washington Streets, just across from the Old South Meeting House.Your tour guide will be waiting for you under the front awning.

With your expert guide, you will set off to explore Boston’s architectural history as revealed by the massive engineering project known as “The Big Dig”.

Your tour guide will begin by discussing the legacy of English architectural and town planning ideals as manifested in the Old Massachusetts State House and Fanueil Hall, two renowned monuments in Boston.

From here you’ll pass by other notable buildings, including Quincy Market, the Custom House, and the nearby warehouse buildings of the Boston Granite School,which together trace the city’s physical expansion along the shoreline.Using historical maps for reference, you’ll see how topography and layout of the city have influenced its present form.

You will be able to understand how successive styles of commercial buildings narrate the city’s economic development during the 19th and 20th centuries, giving rise, eventually, to the construction of a major highway through the city's core in the 1950s.

You’ll learn the story of this highway, and the dozens like it that impacted American cities all across the country from the open greenway that now marks the Big Dig.Your guide will discuss questions of transportation, civic identity, and urban planning along this corridor.

You’ll look at this project’s goals, some of its obstacles, and the ways in which it has transformed the city.A walk along the Big Dig’s corridor of parks, the Rose Fitzgerald Kennedy Greenway , will reveal the multiple incarnations of Boston’s social and physical identities that have defined this area over the last two centuries.

The tour ends in the vicinity of Rose Fitzgerald Kennedy Greenway Park. At the end you should emerge with a deeper understanding of how Boston has changed over the century and how the current city reflects its history.

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Activity Schedule

When does it run?



3 hours

Start time

Start time: 10:00am
Duration: 3 hours

Meeting point

Your tour guide will be waiting under the awning in front of Bruegger's Bagel Bakery at 7 School Street, located at the corner of School and Washington Streets, just across from the Old South Meeting House

Ending point

This tour ends in the vicinity of the Rose Fitzgerald Kennedy Greenway Park.

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  • English-speaking guide – an architectural scholar


  • Hotel pick-up and drop-off
  • Food and beverages


Dress for the weather and wear comfortable shoes for walking. Remember to bring a camera!

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Please note

Please call the activity operator at least 24 hours prior to start of the tour for reconfirming departure details.

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Additional info

  • The confirmation voucher includes the local activity operator’s contact details and local telephone numbers at the destination. They will happily answer any logistical questions you may have.
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Cancellation policy

See the Cancellation policy for this product

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US$ 75.00 Price per person from
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  • Child age

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