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Boston private guides and walking tours


Context's scholar-led walking tours of Boston illuminate the rich history and artistic patrimony of one of America's first and finest cities. From Paul Revere, to John Singer Sargent and the Big Dig, our three-hour walking seminar topics include such themes as:


Big Dig

Public Works and Architecture
Big Dig
Led by a landscape architect or urban historian, our Big Dig seminar delves into one of the largest and most expensive public works projects in history.

Featured Walks in Boston

History Walks (1 of 3)

North End Boston, Portrait of a City

Boston featured walking tour - North End Boston, Portrait of a City

Since its founding in 1630, Boston has embodied many of the historical themes that have shaped America including commerce, political revolution, social innovation, and waves of imm

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Art Walks (1 of 2)

Museum of Fine Arts

Boston featured walking tour - Museum of Fine Arts

Boston's Museum of Fine Arts is one of the country's oldest and most important art museums. With a collection that spans millennia and the globe, the MFA provides an endless opport

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Architecture Walks (1 of 2)

Big Dig

Boston featured walking tour - Big Dig

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 his

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History Walks (1 of 3)

Black Boston: Freedom in the Empire and the Republic

Boston featured walking tour - Black Boston: Freedom in the Empire and the Republic

This three-hour walking tour of Boston examines African American history in the city. Tracing an arc from the North End to Beacon Hill, and from the arrival of the first Africans i

See all 3 History Walks