Friday Flashback #86

Two weeks ago, our Friday Flashback showed the unchanging nature of an important downtown crossroads.

A time traveler from decades ago would have no difficulty today recognizing the Westport Bank & Trust building (though some of the fashions at the present tenant, Patagonia, might surprise her).

Across Church Lane, the transformation of the Westport Weston YMCA into Bedford Square has altered — but not radically changed — the streetscape.

Of course, it did not always look that way.

Here’s a view of Main Street, at what was then called “The Square” (note the horse watering trough in the middle). The building on the right was replaced by the Westport Hotel — which itself was replaced in 1923 by E.T. Bedford’s gift to the town, the YMCA.

(Photo courtesy of Westport Historical Society)

Another view — looking west up the Post Road, toward the Saugatuck River — shows the building on the Main Street corner (on the right) from another angle.

(Photo courtesy of Westport Historical Society)

Check out the trolley. It provided great local transportation, with branches running from downtown to Saugatuck and Compo Beach.

And where was the trolley barn?

Somewhere on Church Lane. So — despite its current unchanging look — that area was indeed different, back in the day.

(Photo courtesy of Paul Ehrismann)

5 responses to “Friday Flashback #86

  1. That’s interesting – a trolley with a cowcatcher! (third picture)

  2. Jonathan Maddock, Staples '73, FRBB Alumnus

    in the 1960’s, prior to asphalt pavement I remember seeing the trolley tracks embedded in the then concrete road surfaces. My dad road the trolleys back in the late 1920’s and 1930’s.

  3. Two things:
    First, was told that trolley barn was on Main Street, near where TD bank is now. That is why the upper part of Main Street’s building fronts sort of bow like that, to allow the tracks enough curve to turn into the barn. Unreliable source, but it makes sense.
    Second, because I love telling this story, George Walter Mills worked as a trolley man. During the blizzard of 1888 the tracks were snowed under. Not going let that stop him from doing his job, especially getting the mail off the train, he hitched up the team and wagon and set to his route with his father Joseph. Well, they picked up their passengers downtown, and got to the train station. Only to find the trains had been snowbound and didn’t make it through for three days.

  4. The trolley barn was, I believe, on Riverside Avenue at Cross Street.

  5. As for the Square where Main St, Church Lane, the Post Rd and Taylor place converge, you may also encounter this area referred to as “Hotel Square” in materials of the time.

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