Friday Flashback #239

As Westport’s downtown renaissance continues, Seth Schachter sends some fascinating postcards from a far different era.

All 3 show “Fountain Square.” The Post Road (then called State Street)/Main Street intersection was as heavily trafficked — for its time — as it is today.

One of the main attractions was a fountain — actually, a horse trough. (“Trough Square” does not have quite the same ring.)

This 1906 view shows the view looking north on Main Street. The first few buildings on the left look similar to today. The Westporter Hotel (right) was replaced in 1923 by the YMCA.

The view below — also from 1906 — looks west on State Street, toward the Saugatuck River and Norwalk. The building in the center of the photo would soon be demolished for — as the postcard says — “the new Jesup Library.” It would be expanded in the 1950s toward the west.

In 1986 the Westport Public Library moved to its present site near Jesup Green; it was replaced by, among other tenants, Starbucks, Freshii and the recently closed Pop’TArt gallery.

In the scene below, similar to the first photo above — probably from the 1920s — the YMCA had already been built (right). A small park outside the library can be seen at the left. The Main Street streetscape is very recognizable.

A horse drinks contentedly from the trough.

And the street is just as rutted as it is now, a century later.

9 responses to “Friday Flashback #239

  1. Jack Backiel

    In the bottom picture, the people standing behind the horse are wearing face masks, like the ones we do today. That probably puts the photo around 1918 or 1919. They were protecting themselves against the Spanish Flu.

    • Seth Schachter

      Jack – great observation!!! That would certainly make sense if it was during that time period.

  2. Jack Backiel

    Seth, Actually all three in the picture have masks. Does anyone know who is on the wagon?

  3. David Jones

    All I see is the Ye Old Bridge grill

  4. Caryl Beatus


  5. Wendy Crowther

    In the bottom photo, the building on the right looks like the Westport Hotel not the YMCA. Therefore, I think Jack B. is correct for many reasons.

  6. Pegeen Gaherin

    David Jones,

    Laughing ๐ŸŒŸ๐Ÿ’™๐ŸŒŸ๐Ÿ’™

    I remember the fountain or is that just a bi-product of spending too much time in the Ships Lantern….
    While attending Staples


  7. Jack Backiel

    In the bottom picture, I think the horse is coming from the Fairfield direction going towards the Norwalk direction. The person driving the wagon is fairly young with black hair. My grandfather had jet black hair, but would have been 37 in 1919, so itโ€™s not him. There were two Italian families I know of who might have farmed back in 1919. Perhaps the person is of Italian heritage. Iโ€™m going to do some research.