One of the hottest topics in Westport — besides whether you will lose power for a week in the next storm, or merely 3 days — is this: How dead is downtown?
A recent news story caught my eye. According to Destination Development International — a community branding company — in order for a place to be a “true destination,” it must have 10 places that sell food, 10 non-chain specialty shops, and 10 places that stay open after 6 p.m. (“preferably entertainment venues”).
I should mention that I read this story in FairfieldCitizenOnline.com. The piece was written by the president/CEO of the Fairfield Chamber of Commerce, and it declared — suprise! — that Fairfield’s downtown meets those criteria. With “a definitive yes,” in fact.
Fairfield “has plenty of restaurants with varied cuisines and within walking or easy driving distance of each other,” Patricia Ritchie wrote.

With specialty shops, restaurants and entertainment -- plus trees, plantings and benches -- downtown Fairfield is a 10-10-10 destination.
There are many specialty shops too. (“Friends from Westport often tell me there is a noticeable difference between the two downtowns,” she jabbed, “mainly because Fairfield has more independent boutique shops, as opposed to national retailers.”)
Patricia hemmed and hawed a bit on entertainment (“after all, [it] is in the eye of the beholder.”)
But she tossed out an admirable list of places that “one can consider entertainment,” starting with Sportsplex near the train station (fencing and cheerleading lessons, rock climbing, skating, martial arts, laser tag, and god knows what else).
Patricia also cited the Fairfield Theatre Company, with “some of the best bands around.” (Upcoming: Christopher Robin Band, Fishhead Stew, and on February 15: John Mayall.)
The Community Theatre — currently closed — may soon be added back into the mix.
Patricia’s points are well taken. How, then, does Westport’s downtown stack up?
We probably have 10 restaurants, depending on the definition of “downtown,” “selling food” (does Starbucks count?), and “open” (2 new places will arrive this spring on Church Lane, and there’s a vacancy around the corner on Riverside Avenue).
We may reach the “non-chain specialty shop” threshold, again by creative definition of “non-chain” and “specialty.” There’s Sally’s Place, the Liquor Locker — whoops, it’s moving — and, um, of course, well, you know…
As for 10 places that stay open after 6 p.m., offering entertainment: Hah! There’s weekend music on Bobby Q’s roof.
There’s the Y — Westport’s answer to Sportsplex. (For a couple more years, anyway.)
And there is — one day, maybe, perhaps — a movie theater. Like Fairfield, we have a building that’s already served that function for many years. Unlike Fairfield, it is now an upscale hardware store.
Yet Westport does have something Fairfield lacks. It’s not downtown — but it’s showing signs of being a true destination.
It’s called Saugatuck.
There are plenty of restaurants — all within stumbling walking distance — and some have live music.
There are a few specialty shops — you don’t see too many kayak chains around — and the promise of pretty cool entertainment. There’s no Sportsplex or Y, but with the new plaza on the river, and 2 more phases of development to come, there’s lots of room for creativity.
At the risk of incurring the wrath of the Westport Downtown Merchants Association, it seems Saugatuck — with its 10-10-10 criteria — is the new cool spot to be.
Who knows? Saugatuck may even become the next Fairfield.

















