1.1 min readBy Published On: December 20th, 2023Categories: Features2 Comments on Remembering Bailey’s Ice Cream Shop

When I was kid, going to Bailey’s Ice Cream Shop was always a special treat.  I remember going after visiting the Enchanted Village at Jordan Marsh at Christmastime.  My mother always made sure my brother and I were dressed up – usually matching Rothschild coats.  We would walk a few blocks in the cold from Winter Street to 45 West Street.  Inside the shop were small marble topped tables with wrought iron legs and chairs.  You ordered your ice cream sundae from a counter and it was served in silver pedestal ice cream bowls on top of silver plates with long spoons.

After your sundae, you would look at the candy in glass display cases.  Sometimes my mother would get a pound of fudge for my grandfather.  For many, it was part of growing up in Boston.  It was a tradition that was passed down for generations.  Sadly, the legendary ice cream shop closed its doors in the late 80’s.

What’s your Bailey’s memory?

History Lesson

Opening in 1873 at 45 West Street, Bailey’s sold candy and ice cream.  The owners were John B. Bailey and D.H. Page.  When Bailey’s first opened, the shop focused on candy but later added ice cream.  Eventually, Bailey’s opened up 11 ice cream shops. 

Image via Dirty Old Boston Instagram 


  1. Judy Silva Nee June 17, 2023 at 8:40 am - Reply

    I think most of us experienced our maiden trips with our mothers , usually with piles of Filenes basement bags around our feet. My mother introduced me to the decadence of a dripping butterscotch sundae where the usefulness of the silver plate upon which it sat was revealed. A glass of water from the self serve water machine – not bubbler – was part of the ritual and I remember it was usually difficult to find an unoccupied table. Later, when I worked at Filenes, I would make the trek for the best chocolate chip ice cream ever ( and a sneak peak at my crush behind the counter!) and I often wondered if anyone ordered the creme cheese and olive sandwich which was still listed in the beautifully hand written menu on the wall. Curses to Joey Crugnale, former owner of Bertuccis and Steve’s, for thinking he could improve on this Boston institution only to bury it. Lots of that going around…

  2. Annie Ryan December 21, 2023 at 1:54 pm - Reply

    My grandparents would make pilgrimage to Boston maybe twice a year. Gramma would wear a good suit, hat, gloves and a scarf. Grampa wore his brown suit and church overcoat. He would gleefully order two hot fudge sundaes and eat my half that I couldn’t finish.

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