Boston to Cambridge: Parks, Brownstones and a Killer Skyline

Boston, MA

  • The downstairs entrance to the Cheers bar. Photo: Cheers Boston.
  • An almond croissant and cup of black coffee at Tatte.
  • The Boston skyline from the Longfellow Bridge.
  • The four towers of the Longfellow Bridge. Photo: Massachusetts Department of Transit.
  • The fountain and garden on top of the Cambridge Center Roof Garden. Photo: Richard Kattman.
  • Google offices overlook the Cambridge Center Roof Garden.

1 hour and 30 minutes
2.3 mi
Guided by Katie D.
Katie Dickinson


Boston is a big city squished into a relatively small space. Many of the popular sites that are “in Boston” are actually in the immediate suburbs. On this walk, we’ll explore some of the charming spots from the city-proper and then head to its most popular neighbor: Cambridge. We’ll stroll through a park, stop for coffee (or tea) in the brownstone-heaven that is Beacon Hill, and finally cross the Charles River for a special view of the downtown Boston skyline.

About Your Guide

Local to the Boston area. Huge proponent of fringe-neighborhood exploration. I blog at - focusing on budget-friendly travel and on-foot exploration.

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Guide Points

  1. Edgar Allan Poe Statue

    Edgar Allen Poe was born in Boston on January 19, 1809. Today we’re looking at the bronze Poe statue by Stefanie Rocknak. This statue of th…

  2. George Washington Statue

    The land you’re standing on right now, and for the remainder of this walk, is fake land. That’s right. In the early 1800s when Boston’s pop…

  3. Make Way for Ducklings

    This charming little statue series by Nancy Schön is a homage to the popular children’s book _Make Way for Ducklings_ by Robery McCloskey.

  4. Cheers

    We come to the bar that inspired the popular 1980s TV show _Cheers._ This is the "place where everybody knows your name."

  5. Tatte Bakery & Café

    This beautiful and delicious café is located in the Charles Street Meeting House. Built in 1807, the building has changed hands multiple ti…

  6. Longfellow Bridge

    We're going to cross the Charles River into Cambridge. It's not a very long bridge, so don't worry about logistics.

  7. Cambridge Center Roof Garden

    I’m drop you off at the doors of the Cambridge Center Roof Garden. Head on up to this secret place to hang out and catch a glimpse of the c…

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