Boston Weekend Highlights

THE GOODS:  On foot in Boston with an afternoon or a day to kill? Check out these highlights, easily doable in a short amount of time.

Last weekend was a whirlwind trip to Boston! I flew out on the red-eye Thursday night, arrived Friday morning about 10am with some delays (ugh US Air, soon to merge with American…).  I spent Friday in Newburyport with my good friend from college, then Saturday and Sunday in Boston.

Boston is such a compact city, it’s easy to find plenty to do without having to go very far or waste time driving around from place to place. You can easily navigate on foot or via the subway (aka the “T.”) Below are some of my highlights and suggestions for what you can do if you have an afternoon or two to spend wandering around.

  • Take the Red Line to the Charles St. Station stop.  From here you will be at the bottom of Beacon Hill. Cross over Cambridge St. and head into the neighborhood behind the CVS, admiring the ancient brick row-house apartment buildings and occasional cobblestone streets along with the beautiful townhomes. Be sure to check out Acorn St., one of the last true cobblestone streets in Boston and “the most photographed street in the world.”

Acorn St., Beacon Hill

  •   Find your way into the Boston Public Garden. It’s bordered at its northwest edge by Beacon St and Arlington St.  Cut into the Garden and roam around, watching the people taking picnics, relaxing on the grass, watching the ducks and duck boats, or walking hurriedly to their next appointment.
The duck pond at the Boston Public Garden

The duck pond at the Boston Public Garden

  • Head to Newbury St. This is the shopping mecca of the Back Bay area of Boston. It’s roughly 8 blocks long, with high-end shops from end to end. If you get bored of the shopping, ask someone for quick directions to Commonwealth (or “Comm” Ave) where you can enjoy the broad French-style boulevards with  mansions on both sides, lined by trees. One of the most picturesque walks in Boston.
Comm Ave

Comm Ave

  • While exploring on Newbury St/Comm Ave., you can walk down one more block south to Boylston St.  Check out the beauty of the glimmering John Hancock Building looking down on Copley Square.


  • On Boylston St between Dartmouth & Exeter, you can also see the Boston Marathon finish line with a makeshift tribute to those who were injured or killed.

Boston Marathon finish line tribute

  • Take the Orange Line “T” to the Haymarket stop and walk into the North End for a slice of pizza in Boston’s historically Italian-American neighborhood.  I recommend Pizzeria Regina; we sat at the small bar, had a Harpoon IPA (my favorite beer ever), and ate a slice while the bartender gave us life philosophies.  I had heard it was touristy, but we were sitting next to some awesome locals who chatted with us as well!  As you stroll the North End, you’ll see plenty of neighborhood color in the locals sitting on their stoop shooting the breeze and watching the passers-by.  If it’s a Saturday, you may even stumble across the massive Haymarket itself, the sprawling farmer’s market where you can get fruits and veggies, cheese, flowers, and even fresh fish including freshly shucked oysters from the local stalls.
The "Connah Stoah"

Local color in the form of “The Connah Stoah”

  • Fanueil Hall, adjacent to the North End, is a must. It’s touristy, but you can still find some fun bars tucked among the obvious tourist places.

You can probably visit all these locations in a single day!  Just make sure you’re wearing comfortable shoes and be prepared for whatever weather might await you.




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