Category Archives: Photo Challenge

Photo Challenge #611

Posted on September 13, 2026 | 4 comments

There are several things you can do when you’re stuck on the Kings Highway North hill, waiting for the Wilton Road light.

You can quietly seethe, inching up on the car in front that can’t go anywhere.

You can concentrate on your audiobook, podcast or (hands-free!) phone conversation.

Or you can gaze off to the left, at the Kings Highway Colonial Cemetery

You can’t see the names from your car. They include Henry Moses Judah, who until 2024 was the last Civil War general in the nation with an unmarked grave; the Taylor family, of the eponymous Taylortown Marsh, across the road; and the Marvins, whose tavern not far away once hosted George Washington.

But you can see a stone monument, with 3 words: “Rest. Enjoy. Protect.” (Presumably they refer to visitors; full-time residents can only follow the first suggestion.)

That photo, by Nancy Breakstone, was last week’s Challenge. (Click here to see.) Morley Boyd, Marie Gross, Diane Silfen, Tammy Guarente, Diane Bosch, Karen Como, Lynn Untermeyer Miller, Sal Liccione, Janice Stirzever, Seth Braunstein, Paul Cahill and Wendy Schaefer apparently spend enough time at that light to have correctly identified it.

Congratulations. Now rest, enjoy and protect!

Here is this week’s Photo Challenge. If you know where in Westport you would see it, click “Comments” below.

(Photo/John Maloney)

(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 #610

Posted on September 6, 2026 | 21 comments

As expected, last week’s Photo Challenge was tough.

Wendy Crowther’s image of a weather-beaten barn could have been a number of places around town. (Click here to see.)

But it can be seen on a walking path at a place some Westporters visit regularly, and others have never been to: Sherwood Island State Park.

Werner Liepolt explains: “It is an equipment barn on the shore of Sherwood Mill Pond, across the little road from the trailer park set for a Donald Sutherland movie based on a Stephen King short story filmed a couple of years ago.

“I know this portion of the barn because when dogs are allowed into Sherwood Island, Pip walks me by this barn every third walk. (He has 3 chosen routes. Go figure.)

“This is believed to have originated as the stable barn of the Sherwood family farm or estate; a nearby stone building reportedly served as the carriage barn.

“The Sherwoods settled on what was then called Fox Island in 1787. They operated a substantial 19th-century coastal farm, growing onions and potatoes for shipment to New York and running the gristmill at Sherwood Mill Pond. The barn is therefore an important surviving link between Sherwood Island’s agricultural past and its later public use.

“After the state made its first small purchase there in 1914 — the beginning of Connecticut’s state park system — it took a contentious 23-year struggle to secure sufficient land and public access in 1937.

“The old farm buildings were subsequently adapted for park maintenance, equipment storage and staff use. A former employee recalled working around the white barn in the 1960s and ’70s, and even living in it one summer.

“Unfortunately, Connecticut’s Department of Energy and Environmental Protection has classified the barn as structurally deficient and unusable for park operations. Its current restoration program lists demolition of the barn as ‘completed,’ and calls for construction of a new, simple metal vehicle-and-equipment storage building, originally estimated at $400,000.

“If the building in this recent photograph remains standing, DEEP’s notation may be premature, or this may be a surviving section of the larger historic service complex.”

Besides Werner, Jeanine Esposito and Joyce Evans correctly identified last week’s Photo Challenge.

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

(Photo/Nancy Breakstone)

(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 #609

Posted on August 30, 2026 | 25 comments

“06880” readers did not “knead” to think long about last week’s Photo Challenge.

The image of a sign saying “Saugatuck” was indeed at Kneads, the bakery, café and “mill” in the heart of that historic neighborhood.

If we gave out prizes, there would be free croissants and cappuccinos for Marc Frankel, John McKinney, Helen Appleby, Brian Taylor, Wendy Schaefer, Robin Jaffee Frank, Seth Schachter, Sal Liccione and Ida B. Lowe.

But we don’t. So “congratulations!” will have to suffice.

Today’s Photo Challenge might be tough. We’ve learned never to underestimate our readers, though.

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

(Photo/Wendy Crowther)

(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, Saugatuck

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Photo Challenge #608

Posted on August 23, 2026 | 9 comments

It’s called the Westport Woman’s Club.

But between hosting town-wide events at its Bedford Hall auditorium, and the wildly popular 1o7-year-old Yankee Doodle Fair, plenty of guys are familiar with the Imperial Avenue property.

Still, I was a bit surprised that about half of the correct responses to last week’s Photo Challenge — a shot of the Woman’s Club’s moderately hidden patio entrance — came from males.

In fact, I was surprised that 8 readers nailed what I thought was an obscure image. (Click here to see.) 

Congratulations to Diane Bosch, S. Jonas, Sal Liccione, Seth Schachter, Kim Reichert, John Hartwell, Rachel Sara Halperin and Samuel Pollack.

If we gave out prizes for this contest, you’d win the stuffed animal of your choice. Just like the Yankee Doodle Fair.

Here is today’s Photo Challenge. If you know where in Westport you’d see this, click “Comments” below.

(Photo/Dan Woog)

(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 #607

Posted on August 16, 2026 | 12 comments

Between the difficulty of the image, and the fact that everyone was outside enjoying the beautiful weather, last Sunday’s Photo Challenge drew a perhaps record-low 6 responses.

And none were correct.

John Maloney’s shot of a wooden fence underneath a stone arch was not from Compo Road South by Appletree Trail.

It was on Riverside Avenue, near Viva Zapata. Click here to see.

No problem. Every Sunday, there’s a new Photo Challenge. This week’s is moderately similar.

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

(Photo/Lauri Weiser)

(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, Saugatuck

Photo Challenge #605

Posted on August 2, 2026 | 13 comments

Many Westporters admire the Gault barn.

Set midway between Post Road East and Bridge Street, on Compo Road South, the handsome red building is a throwback, to days gone by. (And a reminder that the Gault family — whose nearby Saugatuck business dates back to the agricultural and coal-hauling days of the 1800s — remain one of our town’s most beloved, and philanthropic, families.)

But there’s another view of the Gault barn that fewer Westporters see.

Tom Kretsch captured it last week, for our Photo Challenge. His image — with shades of red and tan, narrow windows, and a low stone wall — could have been mistaken for a painting of a long-ago European scene. (Click here to see.)

Tom says, “I have lived in Westport for 52 years. I have walked and jogged by the Gault Barn hundreds of times. Last week I stopped and saw a sign by the Westport Artist Association, with historical information about the barn.

“There was a picture of a painting by an artist whose name escapes me of the back side of the barn. I never knew of this back side.

“I walked down a hill behind the barn, and was astounded by that perspective. I came back another day with more favorable lighting to compose the image.

“What a treasure that building is in this town.”

Twenty readers quickly identified that treasure. Some grew up in Westport. Others are much newer arrivals.

All — like Tom — revere the Gault barn.

Congratulations to Michael Chait, Brian Taylor, Sue Iseman, John McKinney, Morley Boyd, Chip Stephens, Dave Eason, Jen Carpenter, Beth Berkowitz, Seth Braunstein, E. Bruce Borner, Lynn Wilson, A. Starr, Jonathan McClure, Sal Liccione, Tom Wall, Seth Schachter, Nancy Diamond, Matt McGrath and Judi Koffsky.

And for the rest of you: You’ve got one more treasure in Westport to discover.

Here is his week’s Photo Challenge. If you know where in Westport you would see this, click “Comments” below.

(Photo/Janine Scotti)

 

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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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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!)

9 Comments

Posted in Photo Challenge, Restaurants

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