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 image – The Head House in 1906 – From the Library of Congress