1.7 min readBy Published On: August 22nd, 2023Categories: Features8 Comments on Southie History Lesson – The Head House

It may be hard to imagine, but Pleasure Bay was once home to its own beachside resort of sorts, complete with ice cream shops, restaurants, bathhouses, retiring rooms, office space, and cabanas. Located across from Castle Island, the Head House—which opened in 1897—sat at the “head” of a peninsula jutting 200 feet out into Boston Harbor. It sported a unique Tudor-style construction designed by Edmund Marsh Wheelwright, the architect behind iconic Boston structures like Horticultural Hall and the Harvard Lampoon Building. A similar neo-German building—featured at the 1893 World’s Columbian Exposition in Chicago—inspired Wheelwright’s design for the Head House.

In its heyday during the early 20th century, the Head House was quite popular. Per reports from the time, it attracted up to 200,000 daily visitors in the summer—creating parking problems even when few owned cars. Summertime beachgoers who didn’t own cars would spend five cents to take the “Bay View” Trolley line to City Point, bringing their lunches and family with them. Visitors would also often take a trip to the South Boston Aquarium, which was located across from the Head House.

An aerial view of the Head House in Pleasure Bay before it was connected From Flickr

Unfortunately, the economic struggles of the Great Depression took a toll on the Head House, and when the Hurricane of 1938 hit, the building sustained major damage. By the time a fire burned part of the building down in 1942, it was deemed beyond saving and torn down. In the 1950s, a new path connecting Pleasure Bay and Castle Island was built where the Head House’s pier stood.

In a time where Southie is once again a popular summertime destination for inner-city folk, one has to wonder if we’ll see some similar beachside amenities come to the neighborhood. But until then, we’ll have to reminisce on lost beauties like the Head House.

Main imageThe Head House in 1906 – From the Library of Congress



  1. Mike Thomas August 22, 2023 at 1:55 pm - Reply

    And, that must be Kelly’s landing, but what was it in 1906 ?

    What was the purpose of the long walkway behind, and the cul-de-sac?…just a way to get a stretch ?
    It looks like breakers…
    Shane, great to see your work !
    Good luck in the future.

    • Maureen Dahill August 22, 2023 at 3:11 pm - Reply

      The head house was closer to the Sugar Bowl than where Kelly’s Landing used to be. Area next to the head house are the beaches – Pleasure Bay and City Point Beach. Kelly’s landing in 1906 was just a dock for boats to “land.”

  2. Judy August 23, 2023 at 11:14 am - Reply

    Shane . Your Grandmother would be so proud of you.

  3. Peter August 24, 2023 at 2:32 pm - Reply

    I would love to have been able to visit that and see what it looks like inside. Sad to lose a beautiful building like that.

  4. Marion Fennell Connolly August 25, 2023 at 3:44 pm - Reply

    I vaguely remember seeing the head House in 1938 when I was 4 years old. My mother took me in there.

  5. Macca McNeil September 2, 2023 at 10:20 am - Reply

    My brother Paul was born that day my mother and father walked to the hospital

  6. Mary Kilroy September 2, 2023 at 10:49 am - Reply

    Hi Shane,

    Very interesting piece! I notice you chose two words for the name of the route “Bay View.” Would you have any idea what the bus route was called in the 40’s and 50’s. When I lived in the OCHP, and took the bus out of the MTA Broadway Station , I thought the bus was titled “Bayview.” I;m on a deadline, can you or anyone else help me out. Maureen?


  7. Kate Rivera September 14, 2023 at 4:24 pm - Reply

    I remember the “Bay View” Bus; I think it ran along 8th Street; heading toward ; City Point; don’t remember where it turned around, going back the other way. This was in the early 50.s.

    Kate R

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