The Black Duck is a Westport legend.
Between its sloping floor, river view, frequently flooded parking lot and basic but down home menu, “the Duck” never pretended to be anything other than what it was: Westport’s favorite (okay, only) dive bar.
(Don’t believe us? It was immortalized on the “Diners, Drive-Ins and Dives” TV show.)

One view of the Black Duck … (Photo/Lynn Untermeyer Miller)
For decades, the former barge — which always seems ready to sink, yet somehow remains afloat — never changed.

… and another. (Photo/John Videler for VidelerPhotography)
But the age of AI is here.
And it’s everywhere. Including the Duck.
Last weekend, longtime Westporter Scott Smith, his son Cole Prowitt-Smith and Cole’s girlfriend headed to Saugatuck.
She’s from out of town. Cole wanted to show her a genuine Westport landmark.
They sat outside, on the covered deck. As Scott enjoyed the classic view of the Saugatuck River under the I-95 bridge — with action at the boat ramp across the water, and listening to trains rumbling past — Cole showed him the menu.
It was a new design. Scott says, “perhaps I wouldn’t have picked up on it. But since Cole is a Gen Zer working in New York, and very much involved with AI, he pointed out some glaring absurdities with the photos on the cover.”

Black Duck menu. (Photo/Scott Smith)
As he looked closely, Scott saw that every image was “a horrid example of the AI-enshittification of our commerce and culture.”
The small second floor had been transformed into something grand. Ditto the bar.
The outdoor deck had umbrellas, like Longshore.
The sun was setting — to the north! — across what looked like a wide bay.
And, Scott wondered, What happened to I-95?!

The sun sets to the north, across an impossibly wide Saugatuck River. And why, Scott asks, is one couple sitting oddly behind the backs of others?
“The Black Duck has its own beauty and history, right down to the slanted floorboards,” Scott says. “How anyone could sign off on this faux design is beyond me.
“Truth in advertising may no longer be a thing. But how do you square this AI-feverish depiction when you’re sitting in the real Duck?
“You have to laugh. But it’s not really funny.”
(“06880” regularly covers Westport’s restaurant scene — in all its forms. If you enjoy this, or any other features on “06880,” please click here to support our work. Thank you!)
