As anyone who has ventured downtown in the past year knows, Westport is changing.

The Y is long gone. The bones of its Tudor Bedford building remain — enhanced by a wider sidewalk that shows off the handsome 1923 structure — but all around, a new structure rises. Bedford Square, named for the man who helped define downtown Westport, opens next spring. With a mix of retail stores, restaurants and rental units, it will redefine this geographically small, but economically and emotionally vital, part of downtown.

A final piece of the puzzle is in the works. Last week, David Waldman moved one step closer to completing a land swap that could benefit Bedford Square and the rest of downtown. The developer hopes to construct a new $7 million building with retail and residences where the Baldwin parking lot fronts Elm Street. It would replace the structure housing Villa del Sol restaurant, which would be razed and replaced by a parking lot larger than the present one, giving the town nine additional spaces.

This would not be Waldman’s first land swap. A couple of years ago, he moved the 19th-century Kemper-Gunn House across Elm Street to the Baldwin lot. Today, it has been renovated, reconstructed and repurposed as the Serena & Lily store.

Those are all big changes, but they’re not the only ones that reimagine downtown Westport. That seems hard to imagine — after all, how can you reconfigure a place bordered by a river?

Pretty dramatically, it turns out.

For most of the 19th century and through the first half of the 20th, the Saugatuck River lapped up against the backs of Main Street stores. Ships no longer docked at wharves, but the river remained an important presence — yet not an honored one: pipes deposited sewage directly into it.

In the postwar years, as Westport boomed, the need for more parking became clear. What we now know as Parker Harding Plaza (or, to some, Harder Parking) is actually landfill. It seemed like a good idea at the time, though in retrospect, it turned our riverfront into a parking lot.

Across the Post Road, downtown looked different, too. A Little League baseball field sat next to Jesup Green. Next to that was the dump. Hard to believe, but we tossed our garbage smack in the middle of downtown. It smelled. It attracted seagulls. Once, it even attracted Amy Vanderbilt, the etiquette expert who, for reasons I no longer remember, held a tea party atop the trash.

Today, the dump — with adjacent landfill — is the site of the Westport Library. When planning began in the 1980s to move the library there from its original home on the Post Road (where Starbucks, Freshii and HSBC Bank are now), some residents were concerned about methane.

The library has not blown up, but if you’ve noticed, the entrance to the upper parking lot has grown a bit roller coaster-ish. Well, now you know why.

The library is next door to the police station. It’s easy to think the solid-looking building has always been there. But for many years, police headquarters was in a structure a stone’s throw away. The cops shared it with other town officials. That’s right: Our entire town government, plus police, operated out of where Rothbard Ale + Lager is located today.

It should be clear by now the only downtown thing that remains the same is change — that includes the bridge. It seems a logical way to connect the east and west banks of the Saugatuck River. But in the early days, the main crossing point was further north, where the Kings Highway bridge is now.

When the Post Road span was constructed, it swung open to allow vessels through. After a couple of upgrades, it is much wider. Dozens of American flags fly proudly there. Twice a year, on jUNe Day and UN Day, they’re replaced by flags of countries around the world. That’s fitting — the bridge is named for former United Nations advocate Ruth Steinkraus Cohen.

Which brings us back to the main idea of this column: land swaps.

Just across the bridge, the Post Road/Wilton Road/Riverside Avenue corner is one of the worst intersections in the state. David Waldman, the developer planning the Elm Street swap, wanted to do another one here.

He proposed moving the small building at the foot of Wright Street to the former Save the Children property he owns. In return, and for a zoning variance, the town would get a dedicated turning lane onto Post Road West. His request was denied.

Some things don’t change, after all.

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