We’ve posted this image of Main Street before. It’s from the 1962 Staples High School yearbook.
But never with this color, or computer-enhanced graphics.

Eric Bosch — who moved here with his family in the fall of 1963 — sent it along.
To orient yourself: Klein’s department store (far right) became Banana Republic, then (briefly) Oka furniture. Brooks Brothers will soon move in, from its current location a few yards north.
The Townly Restaurant featured a Jazz Age-era mural. It was lost when Klein’s expanded into that space, then rediscovered and hung by Banana Republic. No word yet on whether Brooks Brothers will keep it.
The Mobil gas station — once the site of an annual Christmas party, where food was served on the lowered hydraulic lifts — is now Vineyard Vines.
The hardware store was one of 3 on Main Street.
And of course, traffic flowed in both directions, all the way to the Post Road (aka State Street).
What else do you remember from that era? Click “Comments” to share.
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Gas was 30 cents a gallon at that gas station in the picture.
Fun to see this! I believe the building labeled Tacets later became the Liquor Locker, owned and operated by Harvey Skolnick, who I still bump into on my occasional trips to Westport. Just above was an apartment resided in by my mom’s friend Jeannie Davis, who wrote for the Westport News, and her son Nick, who was a close friend in my teenage years (circa 1972, 10 years later).
Great pic, Eric! Don’t get me started, Dan! Ha! I remember Dorian’s drug store and Achorns, currently in Playhouse Square, but back then on Main Street next to Gristedes. (Fun fact: The drugstores in town rotated being open on Sundays.) I also vividly remember Greenberg’s department store where my mom bought my Girl Scout uniform. A little later, Country Gal opened up a few doors down from Klein’s. I’m not sure I was ever a country gal (I was more of a suburban hippie chick during that era), but the store had great clothes. Like I said, don’t get me started. 😉
Ah bygone days. Kleins (town of Weston office supply house) and the gas station.
Just out view, and on the left side of the street, was the “5 & 10 cent Ben Franklin’s”. I recall getting a Rootbeer soda in a tall frosted glass mug, for just a nickle, at the lunch-counter in the back of the store. Afterwards, two of my 3rd grade classmates and I bought bags of confetti and we ran up the sidewalk singing, Sam Cook’s song “We’re havin’ a party”, tossing our colorful confetti into the air and the people smiled and laughed.
Louis Engel had a stamp and coin store above the Townly.
Wow!! What a shot. It brings back untold memories of Westport. I thought the turquoise and white Metropolitan was mine, until I looked closer and realized it wasn’t mine. I had a convertible!! I miss those days in Westport, where the shop keepers knew you by name, and few if any stores were chains.
Very cool… The traffic light is interesting because there was never a crossroad there. If it was there in 1963, it would have be at a pedestrian crosswalk coming out of the tunnel. I believe Sport Mart had two locations on the left side.