The best-laid plans of Bedford Square may go astray, thanks to -- Westport zoning regulations.

Last month, while commenting favorably on plans for David Waldman's retail/office/residential complex that will soon -- at least, hopefully, sooner rather than later -- replace the Westport Family Y downtown and jazz up the Church Lane neighborhood, Planning and Zoning commissioners wondered whether stores above the ground floor in what will eventually be "the former Y Bedford building" are actually legal.

Apparently, second- and third-floor retail space is legit only if there is a pre-existing use. In other words, if Westporters are used to climbing stairs to shop, that's fine. If they haven't done it before -- see ya.

The second floor of the Bedford building -- the handsome structure that's stood at the corner of the Post Road, Church Lane and Main Street since horses watered at a long trough there -- has always been open to the public. For over 50 years, it was where much of the Y action took place. Dances, classes, meetings -- all happened one story above the main floor (which is itself accessible only by a high flight of stairs).

It wasn't retail though, so Westport's byzantine regulations must be reviewed with Supreme Court-like scrutiny. The P&Z will continue discussing Bedford Square's application on July 17 and 18.

Downtown Westport, meanwhile, boasts enough grandfathered upper-floor businesses to fill a senior center.

The old Klein's building at 44 Main Street was once a bustling place. A second floor was added when the "department store" added office furniture to its line. It's still used -- though not by the current ground floor tenant, Banana Republic. Several dance and exercise studios have cycled in and out. Interestingly, they're on what is actually the first floor -- if you enter through the parking lot behind the (ahem) Y.

For decades, Sport Mart was one of downtown's bustling businesses. It started in Sconset Square -- back when that bore a true Westport name, "Sherwood Square" -- and eventually moved to the west side of Main Street. Sport Mart rode the skiing and tennis booms all the way to a second floor. As far as I know, no customer ever complained about carrying skis and poles down one whole flight of stairs.

Nearby, on the same side of the street, the Gap also rented retail space on the second floor. Actually, there were several Gaps -- for men, women, kids, and family pets -- but they've now been consolidated into one mother Gap.

That store is at 125 Main St., and therein lies a vertical tale. Through the mid-1970s it was the site of Westport Hardware. But one January afternoon the store burned to the ground. In its place rose a three-story behemoth (four, including the basement level accessible from Parker Harding Plaza). Retail stores galore wound around a central atrium, staircase and elevators.

I would describe some of them here, but there is only one problem: Neither I, nor any other human being in the history of shopping, ever shopped there.

Perhaps those stores were interesting, and cool and unique. Perhaps they were not. But all are lost to history, because they never advertised, never got out into the community, never left 125 Main Street. Maybe the stairs were too daunting.

At any rate, the Gap is there now. It does a brisk business, filled with folks shopping in its various three-story departments (men, women, kids, family pets).

And if all that Gap shopping makes you hungry, head to the new Cru restaurant in what we should probably not call the basement of the building. (It also has pop-up dining in the parking lot -- hats off to the P&Z, which recognizes the need for creative uses of space to help bring life downtown.)

A couple of other restaurants also enjoy second-floor, pre-existing use status. There's Acqua, which for many years has offered diners wonderful river views. Its father was a Mexican restaurant; its grandfather was Mark's Place, a music club. (One of many, back in Westport's day.)

Tavern on Main is another second-story restaurant. It may be Main Street's oldest same-use space. Tavern's predecessor was Chez Pierre, a French restaurant founded by, I believe, the Marquis de Lafayette.

Farther north -- just beyond Avery Place -- a slew of second-story businesses abound. That's the "Sally's Place" shopping center. And if Sally's lacks customers, it's because the CD industry is dying, not because of Sally or her stairs, for sure.

I'm sure I've missed some places. In fact, I just thought of iFloat -- the great flotation therapy center, with four sensory isolation tanks. It's on the second floor, right above Oscar's. And if town officials are fine with having four pretty heavy water-filled tanks hanging over a delicatessen, they will probably find a way to welcome a couple of retail businesses into a downtown district that is on the cusp of some sorely needed change.

Dan Woog is a Westport writer, and his "Woog's World" appears each Friday. He can be reached at: His personal blog is www.danwoog06880.