Tour of Old Cambridge

In 1630, Cambridge was established as the capital of the Massachusetts Bay Colony. Since then, it has hosted intellectuals, literary geniuses, celebrities, and an incredible array of wealth and power. Few of America’s elite have not spent some time at Harvard, and their contributions to the city of Cambridge have left a lasting imprint.

Stroll the peaceful back streets of Harvard Square and Brattle Street, and see where the early life of T.S. Eliot played out, where Henry Wadsworth Longfellow loved and lost, and where Helen Keller went to class each day. Stories of Puritanical trials, British Loyalists, poetic giants, and Curious George mix with beautiful architecture and well-manicured green space. This tour is a chance to see small town New England just a few T stops from downtown Boston.


  • Winthrop Park
  • Red House/Retaining Wall
  • Old Well
  • Brattle House
  • Dexter Pratt House aka The Village Blacksmith
  • H.A. and Margaret Rey House
  • TS Eliot House
  • Continental Surgeon General
  • Headquarters/Henry Vassal House
  • Washington’s Headquarters/Henry Wadsworth Longfellow House
  • Episcopal Divinity School
  • Radcliffe Yard
  • Cambridge Common/Washington Elm
  • Christ Church
  • Cambridge Burying Ground
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  • Private tours begin at $300, which covers up to 10 guests for up to two hours.​
  • For tours longer than two hours, groups under 10 guests are $150 per hour per guide.
  • For customized tours in groups larger than 10, please contact us for pricing.​
  • ​This tour can be delivered in Corporate attire or Victorian-era Dress, as requested.


  • This tour is designed to blend seamlessly with our Tour of Harvard.
  • The Longfellow House/Washington’s Headquarters offers tours for free through the National Park Service. We are not allowed to give tours on the property, but would be happy to accompany you to a tour through their rangers.
  • Harvard’s Admissions office is in Radcliffe Yard. Let us know if you want to make a stop at it, or if you’d like it pointed out.
  • The Cambridge Center for Adult Education has event space and personal chefs for rent for the corporate client interested in such an activity.​
  • We are happy to make food and drink recommendations for your party’s needs. Please contact us so we can make the best recommendation for your group.

We Can't...

  • We cannot arrange visits into personal homes or gardens.
  • We cannot give tours inside the Longfellow House, or inside any Radcliffe buildings.