Category Archives: Photo Challenge

Photo Challenge #567

Posted on November 9, 2025 | 20 comments

Compo Road South is one of Westport’s most traveled streets.

Drivers slow down as they approach the stop sign at Soundview Drive, before South Compo turns into Hillspoint Road.

Coming the other direction, they still drive slowly. (Hopefully.)

Still, only 5 readers (Dan Vener, Andrew Colabella, Matt Murray, Seth Schachter and Sal Liccione)recognized last week’s Photo Challenge — John Maloney’s image of a rounded, orange-ish door, set among a lattice fence — as #324.

Click here to see. And check it out the next time you’re near the beach.

Here is this week’s Photo Challenge. If you know where in Westport you’d see this probably-outlived-its-usefulness scene, 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!) 

20 Comments

Posted in Photo Challenge

Tagged

Photo Challenge #566

Posted on November 2, 2025 | 6 comments

Sal Liccione was the first reader to answer last week’s Photo Challenge.

He was correct: JD Dworkow’s image showed the entrance to a small apartment building behind Jeera Thai and Finalmente restaurants, on the Post Road. The entrance is on Church Lane. (Click here to see.)

Sal should know. It’s behind his own apartment, opposite Bedford Square.

Two other readers — both of whom do not live in the area — knew the location too: Amy Schneider and Seth Schachter.

This week’s Photo Challenge shows a very different door. If you know where in Westport you’d see this, click “Comments” below.

(Photo/John Maloney)

6 Comments

Posted in Downtown, Photo Challenge, Real estate

Tagged ,

Photo Challenge #565

Posted on October 26, 2025 | 9 comments

From one end of town (Tacombi) to the other (Mexica), Westport has several Mexican restaurants.

But only one has a sombrero on its roof.

That’s Cuatro Hermanos (not “Quatro,” as most readers spelled it). (Click here to see the photo.)

Our much smaller version of the infamous South of the Border restaurant (aka “tourist trap”) on I-95 is located near our own stretch of 95: on Saugatuck Avenue, at the foot of Sunrise Road.

(I have not driven through South Carolina in a while. I don’t know if Pedro, their culturally offensive mascot, is still there. Or their borderline racist billboards.)

Alert, well-fed readers who correctly identified Pedro — er, 4 Brothers — are Andrew Colabella, Bryan Schwartz, Dan Vener, Regina Kiska, Seth Schachter, Sal Liccione, Martha Witte, Michael Szeto, Dave Eason, Seth Braunstein, Sean Liberty and Tom Olson.

¡Felicidades!

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

(Photo/JD Dworkow)

(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, Saugatuck

Tagged

Photo Challenge #564

Posted on October 19, 2025 | 20 comments

Last week’s Photo Challenge was quite location-specific.

Unless you live in the extreme northeast corner of Westport — near where Cross Highway dips into Sturges Highway — or unless you spend a lot of time driving to, say, the Patterson Club — you would not have know that spot, where what may be our town’s saddest and loneliest stop sign sits. (Click here to see.)

Mark Yurkiw, Lynn Untermeyer Miller and Shawn Liberty — at least 2 of whom have homes nearby — were the only 3 to respond correctly.

I’ll try to make up for that sometime soon. Maybe Saugatuck Shores …

Meanwhile, it’s interesting that neither Cross nor Sturges is an actual “highway” — at least, not in the modern sense of the word.

But the term originally meant simply a main, direct road connecting towns. Back in the day, these were major thoroughfares.

Without the need for even a flimsy stop sign.

Here’s today’s Photo Challenge. If you know where you’d see this, click “Comments” below. HINT: Though it’s near I-95, it’s not at South of the Border.

(Photo/DinkinESH Fotografix)

(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!)

20 Comments

Posted in Photo Challenge

Tagged ,

Photo Challenge #563

Posted on October 12, 2025 | 8 comments

“06880” readers skated around last week’s Photo Challenge.

John Maloney’s image showed an old-looking sign, headed “Playground Rules.” They included “Adult supervision required,” “No horseplay,” “Do not use when playground is wet,” and “No bicycles, roller skates or skateboards permitted.” (Click here to see.)

Because the sign looked timeworn, answers included the playgrounds behind Town Hall, and at Luciano Park.

Nope! Surprisingly, it hangs at the most popular playground in Westport: Compo Beach. Thousands of Westport parents, grandparents, nannies, au pairs and other caregivers are very familiar with the recently renovated spot.

But no one — except the very observant Andrew Colabella — knew that the sign is right there, in plain view, on the boardwalk near the swings and other playful paraphernalia.

So I guess not many people know the Compo Beach playground rules.

“Shoes are required.” “No pets allowed.”

And one that’s not on the list, but should be: “Have fun!”

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

(Photo/Jonathan Alloy)

(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!)

8 Comments

Posted in Beach, Photo Challenge

Tagged

Photo Challenge #562

Posted on October 5, 2025 | 12 comments

It seems like our Photo Challenges are either very easy. Or very hard. We seldom hit the Goldilocks sweet spot

Last week’s was particularly difficult. Nancy Breakstone’s image showed a hard-to-figure-out view of an “Open” sign. Most readers figured out it was a restaurant.

Yet only the very persistent and observant Andrew Colabella knew it was taken from Emmy Squared, looking into Anthropologie. Click here to see the shot that stumped nearly everyone. 

Does this week’s Photo Challenge meet the elusive “just right” standard?

If you know where in Westport you’d see this, 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!)

12 Comments

Posted in Local business, Photo Challenge, Restaurants

Tagged ,

Photo Challenge #561

Posted on September 28, 2025 | 8 comments

“06880” readers sure know their sh–.

It took only a few seconds for the responses to last week’s Photo Challenge — the “Free Composted Straw/Manure” pile at Wakeman Town Farm — to pour in. (Click here to see.)

Lou Weinberg, India van Voorhees, Shawn Liberty, Andrew Colabella, Rob Hauck, Seth Schachter, Jen Dumonceau, Arthur Hayes, Cat Malkin and Micheal Simso all answered quickly, and correctly.

Today’s Photo Challenge is less natural than a compost heap. Whether it’s easier or tougher — let’s see.

If you know where in Westport you’d find 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!)

8 Comments

Posted in Environment, Photo Challenge

Tagged

Photo Challenge #560

Posted on September 21, 2025 | 11 comments

Who knew that there are not one but two businesses in Westport whose logo shows an old-fashioned carriage?

One is the Higgins Group, a high-end real estate firm in Bedford Square.

The other is Christie’s Service. the well-regarded auto repair shop next to Gruel Britannia on Cross Highway.

Most readers thought last week’s Photo Challenge showed the downtown company. Their logo, though, includes a horse leading the carriage.

Christie’s does not. (Click here to see.)

After several wrong (Higgins) guesses, only 2 readers — Andrew Colabella and Martha Diamant — nailed it.

This week’s Photo Challenge is below. 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!)

 

11 Comments

Posted in Local business, Photo Challenge

Tagged ,

Photo Challenge #559

Posted on September 14, 2025 | 9 comments

So much for Sherwood Island State Park being a Westport “secret.”

A near-record 28 readers nearly instantly answered last week’s Photo Challenge. Joanna Keyser Rossi’s photo showed a remote-controlled model airplane, flying above the field that — who knew? — so many Westporters know and love. (Click here to see.)

Congratulatiosn to Ed Simek, Susan Iseman, Pat Saviano, Andrew Colabella, Jeff Wieser, Erik Østbye, Jerry Kuyper, Seth Schachter, John McKinney, Seth Braunstein, Sal Liccione, Jack Krayson, Robert Mitchell, Amy Schneider, Lynn Wilson, Jill Brody, Richard Hyman, Bruce Geller, Joyce Barnhart, Jalna Jaeger, Beth Berkowitz, Alicia Kronick, Lynn Untermeyer Miller, Paul Cahill, Clark Thiemann, Matt McGrath, Jon Sinish and Brooks Sumberg.

You’re flying high!

This week’s Photo Challenge promises to be a tad bit harder.

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!)

9 Comments

Posted in Beach, Photo Challenge

Tagged

Photo Challenge #558

Posted on September 7, 2025 | 31 comments

Last week’s Photo Challenge — a whimsical clock, resembling a coffee cup — hit the spot with several readers. (Click here to see.)

It can be found at Coffee An’, the long-lived, much-loved breakfast-and-more spot on Main Street, heading out of town.

Coffee An’ has been there for decades. It’s seen the gas pumps in the parking lot go, along with Ace Hardware next door, and a passel of restaurants across the street. (Hudson Malone seems to have staying power.)

Coffee An’ is such a part of Westport, in fact, that one reader — Todd Suchotliff — answered the Photo Challenge while actually sitting inside.

Others who knew exactly where the coffee cup clock (and great coffee) can be found were Lynn Untermeyer Miller, Jonathan McClure, Ali Godfrey Woods, Seth Schachter and Andrew Colabella.

We move outside for this week’s Photo Challenge. If you know where in Westport you’d see this, click “Comments” below.

(Photo/Joanna Keyser Rossi)

(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!)

31 Comments

Posted in Local business, Photo Challenge

Tagged