In 2018, there are two Americas.

There’s the America of Donald Trump. The president’s supporters are sure he’ll Make America Great Again. He will bring back lost jobs, build a wall, halt the influx of foreigners, save the country from its horrible lurch toward liberalism.

His opponents are equally sure he will Tear America Apart. He will destroy our standing in the world, demolish our values and heritage and constitutional principles, widen the gap between the very few haves, and the very many have-nots.

Westport is nowhere near as divided as the nation. But if you look closely — if you poke a bit beyond the storefronts of Main Street, the beaches and Longshore, the houses and stone walls and security gates — you’ll see a tale of two Westports.

I was reminded of that last week. In the course of two hours, I had two very different conversations. The subject was the same: our community. But the perspectives I heard were vastly different.

The first conversation was with a guy who recently moved here from New York City. Like so many newcomers, he and his family were attracted by the schools, Compo, restaurants, shopping, the library, our arts scene, volunteer organizations, beauty, tempo, and a vibe of activity, acceptance and neighborliness they did not sense in other Fairfield County suburbs.

The second conversation was with a longtime Westporter. She recently moved away, to the Black Rock section of Bridgeport. She’d had it with this place. The traffic, rudeness, hollowing out of downtown, materialism, pressures on kids, tear-downs, lack of interest in cultural and artistic institutions all became too much. Regretfully, she and her empty-nest husband are outta here.

I like and respect both people. I understand both viewpoints, and see merit in each. Westport is not the paradise new arrivals think they’ve found, and it’s not the dystopian hellhole ex-residents imagine. It’s someplace, somehow, in between.

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Dan Woog


The two Westports stand in stark contrast to each other in Saugatuck. The William F. Cribari Bridge — a 130-year-old swing span named for a beloved traffic cop who epitomized an earlier two-Westport era, moving commuters to and from the train station through a neighborhood filled with men and women who worked here — faces questions about its future. Residents fiercely debate its fate: renovation or replacement?

Renovation would mean keeping the bridge — and, by extension (literally and figuratively) the roads leading to and from it — the same. It would be narrow, slow, slightly scary to navigate. It still might be closed from time to time, allowing boats to pass underneath.

Replacement would mean opening it to larger vehicles — including 18-wheelers. Boats could easily pass by. So could overflow traffic from I-95.

What do Westporters want: tradition and a slow, clunky way to and from Saugatuck? Something new and modern, with the potential for even more traffic than today? What are the upsides and downsides, the tradeoffs we make and the compromises we accept? Most importantly, who decides and pays: Westport, or the state? Those are decisions we must make soon.

Another question looms: Are we still an arts community? We’ve got a town arts curator — how many ’burbs can say that? We have a decades-old Westport Arts Center, and a much newer Westport Arts Collective. The Drew Friedman Community Arts Foundation draws on a $1 million bequest to provide education and opportunities to budding young artists. New galleries pop up all over town, from CronArt in Bedford Square to Paddlecourt on Saugatuck Avenue.

Yet there’s no denying: We are no longer a town whose artists, illustrators and painters put Westport on the artistic map. Men and women still work in home studios, but nowhere close to the numbers when members of our “artists colony” created magazine covers, postage stamps, books, cereal boxes and works hanging in museums around the world.

Does that mean that the hedge fund mentality has taken over? We’re now home to Bridgewater — the largest in the world — which served as the inspiration for the dead-on Showtime series, “Billions.” Other hedge funds are headquartered here, and who knows how many directors and managers of funds based elsewhere live here?

How much have their values seeped into — and shaped — our town? Have they supplanted, or merely added to, the values of an arts community?

We’ve seen the two Westports exposed in controversies over changes at Compo Beach too, from the vistas we may or may not lose, to the new bathrooms that may or may not be needed. And we’ve seen them in debates over affordable housing and changes downtown too.

Controversy over Westport’s direction is not new. Generations before ours grappled with what Westport is, and who it belonged to.

The only thing constant is change. Heraclitus said that — in 500 B.C. He’d feel right at home in Westport today.

Dan Woog is a Westport writer, and his “Woog's World” appears each Friday. He can be reached at His personal blog is