No, this is not an April Fool’s story.
It’s a legit question.
For years, we’ve discussed the pros and cons of a parking deck at the Baldwin (Elm Street) lot.
But what about another site: Parker Harding Plaza?
Parker Harding Plaz
It’s not my idea. It comes from Steve Levin. The 1971 Staples High School graduate has spent his professional career in commercial real estate.
He does not live in Westport. But — like many former residents — he keeps up with the town through “06880.”
The other day, Steve asked: “Has anyone considered double-decking the lot? It could easily double the parking there.”
I told Steve I’d never heard anyone propose that. I asked for more. He said:
“Aesthetics can be resolved with proper and sensitive architecture and planting. It’s not like Westport needs to protect the view of the Saugatuck River from the back of Main Street’s retail buildings, nor if properly designed, would it be an eyesore from across the river looking back at the backs of Main Street. And walking along the river would not be impacted.”
Another view of Parker Harding. (Drone photo/John Videler for Videler Photography)
Steve is a bright guy. But this is 2026. I went to an even brighter source: AI.
ChatGPT quickly provided a “conceptual parking capacity & layout” plan, with 160 to 180 spots on the ground level, and 140 to 160 above that. “Compact parking and angled layouts can increase capacity,” it added helpfully.
The AI agent also suggested an elevator and stairs, crosswalks and protective bollards, bike racks, wayfaring signs, exterior screening (“perforated metal, decorative concrete or architectural panels, to reduce visual bulk”), landscaping, and “lighting and signage to match Westport standards.
Of course, this being AI — not a human, but simply software that has never set foot in Westport — there was also this idea, which makes zero sense: “possible access via Church Lane or side street for service vehicles and deliveries.”
No matter how creative a parking deck at Parker Harding is, it can’t be accessed via Church Lane.
ChatGPT also thinks Main Street is the same as Post Road East.
ChatGPT’s plan for Parker Harding: a top level (top), and ground level (middle and bottom). But look closely: the Post Road and Church Lane are misplaced. What is “Parker Island”? “Parking Star Rivers”? And the circulation pattern seems a bit Escher-esque.
So no, we won’t be using artificial intelligence to design a parking deck.
But what about the rest of the idea? Is it completely ludicrous, or something to put on the table?
Perhaps it’s one more thing for the new chair of the Downtown Plan Implementation Committee — whoever he or she is — to think about.
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