Category Archives: Photo Challenge

Photo Challenge #604

Posted on July 26, 2026 | 24 comments

In the dog days of summer, last week’s Photo Challenge featured a close-up of a painting with 2 dogs (click here to see).

Appropriately, they decorate the back of the bus shelter in front of Schulhof Animal Hospital.

Steven Engel, Andrew Colabella, Robert Mitchell, Nancy Diamond, Lesley O’Connell, Carmela Kaufman and the semi-appropriately named Cat Malkin all slowed down enough on Post Road West to correctly identify the image.

This week’s Photo Challenge looks almost like a painting. If you know where in Westport Tom Kretsch captured this shot, click “Comments” below.

(Photo/Tom Kretsch)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Posted in Local business, Photo Challenge

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Photo Challenge #603

Posted on July 19, 2026 | 15 comments

Winslow Park is Westport’s — maybe Fairfield County’s — favorite dog park.

Before its most recent run though, it was other things: a sanitarium (for half a century) — and before that, one of the most elegant estates in town (here’s looking at you, State Senator Henry Richard Winslow, and your wife Mary).

Where not sure when, why or by whom a wrought iron fence was erected on the Compo Road North side of the property.

But it sure looks like it’s been there a while. It was the subject of last week’s Photo Challenge (click here to see). 

Nearly every reader who responded nailed it: Marilyn Alger, Rachel Sara Halperin, Ed Simek, Morgan Eklund, Jonathan McClure, Seth Braunstein, Martha Witte, Lynn Untermeyer Miller and Clark Thiemann.

There were only a couple of errant guesses (Haskins Preserve, and Christ & Holy Trinity Church). Good ideas — but not the right fence.

Meanwhile, we head into the dog days of summer with this week’s challenge:

(Photo/John Maloney)

If you know where in Westport you’d see this, click “Comments” below.

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Photo Challenge #602

Posted on July 12, 2026 | 13 comments

Many Westporters know and love the Riverwalk. That’s the path that begins at the Saugatuck River by the Library, and circles around behind the Levitt Pavilion back toward the pedestrian bridge near the Imperial Avenue parking lot.

Many others have no idea the spot — with wonderful views of the River and Deadman Brook — is there.

Yet even those who know (and walk) it may not realize that the section beginning at the Levitt Pavilion steps is named for Jeff Shoup.

He’s a 1972 Staples High School graduate, who died way too young.

A plaque honoring him was the subject of last week’s Photo Challenge. (Click here to see.)

Everyone who answered — Carol Christiaanse, Seth Schachter, Lynn Untermeyer Miller, Mark Soboslai, Sal Liccione, Amy Schneider, Dan Ashley, Joelle Malec and Jonathan McClure — knew exactly where it was.

When you get a chance, the rest of you should walk it too.

In the meantime, here is this week’s Photo Challenge. If you know where in Westport you’d see it, click “Comments” below.

(Photo/Johanna Shields)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Photo Challenge #601

Posted on July 5, 2026 | 9 comments

There are only a few pay phones left in Westport.

But there are enough so that not everyone dialed in correctly with last week’s Photo Challenge answer.

The image showed the relic behind the bar at Romanacci’s train station restaurant. (Click here to see.)

Dave Eason, Rachel Sara Halperin, John McKinney, Michael Calise and Andrew Colabella all nailed it. Incorrect responses included Sherwood Diner and Dunville’s.

This week’s Photo Challenge shows — obviously — the Jeff Shoup Walk. But where is it?

  (Photo/Bob Mitchell)

If you know, click “Comments” below.

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Posted in Photo Challenge, Restaurants

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Photo Challenge #600

Posted on June 28, 2026 | 10 comments

For decades, a rooster has served as the symbol of the Westport Country Playhouse.

It stands proudly atop the historic theater — as Dan Vener, Elaine Marino, Wendy Crowther, Susan Iseman, Lynn Untermeyer Miller, Rachel Sara Halperin, Bill Scheffler, Seth Schachter, Wendy Schaefer, Sal Liccione, Paul Cahill and Robin Friedson all knew, identifying last week’s Photo Challenge. (Click here to see.)

The rooster also perched for years on a sign above the Post Road entrance. After the 2005 renovation, it was unceremoniously dumped into a back corner of the parking lot. Eventually, the sign — and the rooster — disappeared.

But why a rooster?

I always figured it was had something to do with the Playhouse’s past life, as a barn.

To be sure, I asked ChatGPT.

I was right. The all-knowing (and usually correct) AI tool said: “The rooster is associated with the Westport Country Playhouse because of the building’s origins as a rural New England barn and its long identity as a ‘country playhouse.’

“The Playhouse occupies a historic structure that began life as an 1835 tannery, later became a cider mill, and eventually stood as an abandoned barn before being converted into a theater in 1931. The rooster weather vane atop the building became a natural emblem of that barn-and-farm heritage and has remained one of the Playhouse’s most recognizable visual symbols.

“While the Playhouse’s official history doesn’t appear to give a specific written explanation for why a rooster was chosen, the rooster itself is a classic New England weather-vane figure. Rooster weather vanes have traditionally adorned barns, farm buildings, and church steeples for centuries, making them an especially fitting symbol for a theater housed in a converted country barn.”

There you go. Generations of Westporters have known — and loved — both the Playhouse and its rooster.

If you’re new to Westport — or even been here a while — and have not yet checked out this historic and cultural gem: What are you waiting for? Click here to learn more.

Once you’ve done that, check out this week’s Photo Challenge. If you know where in Westport you’d see this, click “Comments” below.

(Photo/Seth Schachter)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Posted in Photo Challenge, Westport Country Playhouse

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Photo Challenge #599

Posted on June 21, 2026 | 13 comments

The Texaco sign that stood proudly — if a bit faded — for decades near Sunny Daes is gone.

But a proud lion carved into the side of an adjacent building — for many years, Da Pietro’s restaurant — is still there.

That was the subject of last week’s Photo Challenge. (Click here to see.)

Edward Cribari, Jonathan McClure, Dave Eason, Amy Schneider, Sal Liccione, Clark Thiemann, Robert Mitchell, Beth Berkowitz Nell Mullen and Laurie all knew the Riverside Avenue answer.

This week, we move from a lion to a rooster. If you know where in Westport you’d see this, click “Comments” below.

(Photo/Judith Katz)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

 

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Photo Challenge #598

Posted on June 14, 2026 | 12 comments

Last week’s Photo Challenge was not very challenging.

A full 2 dozen readers quickly — and correctly — identified the blue object in Bruce McFadden’s image as one of the unique dome lights at the Levitt Pavilion. (Click here to see.)

Nice to know that Elaine Marino, Joyce Barnhart, Jan Carpenter, Brian Taylor, Seth Schachter, Lynn Untermeyer Miller, Susanne Atkins, Jonathan McClure, Katie Carmody, Diane Silfen, Pete Powell, Richard Hyman, Arthur Hayes, Sal Liccione, Susan Iseman, Lisa Hayes, Amy Schneider, Paul Cahill, Seth Braunstein, Darcy Sledge, Beth Berkowitz, Rachel Sara Halperin, Matt McGrath and Cat Malkin are not just fans of the outdoor theater.

They’re also very observant.

Is today’s Photo Challenge any tougher?

We’ll see.

If you know where in Westport you’d find this, click “Comments” below.

(Photo/Ken Bernhard)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Posted in Entertainment, Photo Challenge

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Photo Challenge #597

Posted on June 7, 2026 | 25 comments

Two decorative spheres — one on each side of the entrance road — greet visitors to Longshore (or “Longshore Club Park,” as no one except town officials call it).

One of them was the subject of last week’s Photo Challenge (click here to see).

It was an easy one. Seth Schachter, Diane Silfen, Brian Taylor, Jonathan McClure, Ed Creevy, Lynn Untermeyer Miller, Michael Szeto, John McKinney, Pat Saviano, Matt McGrath, Amy Schneider, Seth Braunstein, Andrew Colabella and Tom Feeley all checked in quickly with the right answer.

FUN FACT: For decades, a pair of small “foo dogs” (also known as “Chinese guardian lions”) sat behind the marble globes. How and why they go there were mysteries, but the few folks who noticed them always wondered.

In 2022 (or perhaps earlier), they disappeared. They’ve never been seen again. Click here for that “06880” story.

There’s no great back story behind today’s Photo Challenge. But if you know where in Westport you’d see this, click “Comments” below.

(Photo/Bruce McFadden)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Photo Challenge #596

Posted on May 31, 2026 | 17 comments

The “baron’s mansion” — the building at the crest of a hill on Baron’s South, the largely overrun park between Compo Road South and Imperial Avenue — was the subject of last week’s Photo Challenge. (Click here to see.)

Built in the 1950s for Baron Walter Langer von Langendorff — the perfume executive behind Golden Shadows, for whom his home was named — it is hardly a “mansion.”

And anyone who has been inside, and seen the linoleum flooring and green wallpaper — knows that taste is, um, subjective.

But the building — and his property, bought by the town 30 years ago, still undeveloped — have long been part of Westport’s history, and imagination.

The park — though not his “mansion,” and other buildings — are open to the public, from dawn to dark. If you’ve never hiked the property, it’s worth a visit.

Dave Eason, Morley  Boyd, Lisa Hayes, Sal Liccione, Paul Cahill, Matt McGrath, Seth Braunstein, Seth Schachter, Andrew Colabella, Lynn Untermeyer Miller, Martha Witte and Dana Kuyper have obviously all been there. They correctly identified last week’s Photo Challenge.

What about this week’s? If you know where in Westport you’d see this, click “Comments” below.

(Photo/Ed Simek)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

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Photo Challenge #595

Posted on May 24, 2026 | 17 comments

Westport is — or was — a “Tree City USA.”

We’ve got a sign to prove it.

It’s right there on Jesup Green.

But 1) the honor might be outdated, and 2) not many people ever notice the sign. (Click here to see.)

Morley Boyd, Lynn Untermeyer Miller, Robert Mitchell and Sal Liccione were the 4 who did, when we posted last week’s “Photo Challenge.”

And no one offered up a back story about it.

So it’s on to this week’s puzzler.

If you know where in Westport you’d see this, click “Comments” below.

(Photo/Amy Schneider)

(Every Sunday, “06880” hosts this Photo Challenge. We challenge you too to support your hyper-local blog. Please click here to make a tax-deductible contribution. Thank you!)

17 Comments

Posted in Downtown, Environment, Photo Challenge

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