Remember Town Squire?

That was a restaurant from the 1970s. Or maybe the ’80s — who remembers clearly? What I do recall is that it was located fairly near the current downtown Starbucks. It was bare-bones basic: coffee and eggs for breakfast, burgers for lunch. There were no frills, but you didn’t need them. If you wanted to meet someone downtown — for business, to catch up, whatever — you said, “Town Squire.”

There is no Town Squire anymore. Soon, there won’t be a Bobby Q’s. And if you’re looking to talk about why Westport’s downtown is in the shape it’s in, there’s your answer. Our casual dining options are down to zero.

Sure, there’s still Oscar’s. It’s a downtown fixture since the Truman administration, and because owner Lee Papageorge owns his building, it’s not going anywhere. But Oscar’s is a deli, not a restaurant. It closes in late afternoon. It’s not Town Squire.

And, yeah, folks meet at Starbucks. I don’t know why — the tables in the back are dark (and the view of the Post Road is not particularly pleasant). The service is excruciatingly slow. The lines are always long.

Scratch that. I do know why. There’s no place else to go. (Okay, Freshii. It’s healthy and crunchy. But it’s not really a restaurant, is it? More like take-out. Plus, it’s hard to tell someone to meet you at a place whose name you’re not sure how to pronounce.)

Bobby Q’s occupied — and still does, at least through the end of March — an important space in our downtown life. It was a spot everyone knew. It offered good, fun food, at non-eye-popping prices. Kids doodled on the tablecloths.

It opened early, so Sunrise Rotary could meet there. It stayed open late, so we could hang out and hear live music. (Summertime on the roof was particularly fun.) Bobby Q’s, in other words, offered an actual reason for Westporters to go downtown (beyond picking up one more pair of women’s shoes or yoga pants).

Bobby Q’s was also that increasingly rare business: one with local roots. Owner Bob LeRose understood that he ran more than a restaurant. He was part of the town, with an obligation to give back to the people who ate his pork and drank his beer.

He was a driving force in the Westport Downtown Merchants Association. He helped organize the wildly successful Blues, Views and BBQ Festival. He supported our police officers and firefighters. And whenever any local sports team, school club scout troop asked for a program ad, donation or gift certificate, he said “sure!”

That’s not the case with most other Main Street shops and stores. They are in Westport, but they are not of it. Their windows list other chic addresses: Greenwich, Palm Beach, Beverly Hills. Their rotating casts of managers can’t be bothered to take part in civic stuff. Anyone asking for help gets referred to someone higher up, who seldom says yes.

So this is Westport, 2016: a ton of the same type of stores. None with hometown roots. And a crushing lack of options for a good, relaxing meal. In other words: No reason to stay downtown during or after shopping. And no reason to go there once the shops have closed.

(I know, I know. There’s Tavern on Main and Acqua, along with just-opened Rothbard Ale + Larder. But they’re not Bobby Q’s. Or Ship’s, another late, oft-lamented spot to meet and hang. It’s not Tiffany. And if that doesn’t tell you something about where downtown Westport is today, nothing does.)

Main Street did not always roll up the sidewalk at night. The movie theaters brought people downtown. Before and after shows, they strolled up and down Main Street. Music beckoned from several venues — including the second-story Mark’s Place disco. There was synergy, energy, life.

Today there is — well, a new sidewalk. Some new lights.

They’re nice. The Westport Downtown Merchants Association and town are to be commended for this project. It’s made Main Street more attractive. But aesthetics alone won’t make it a destination.

A healthy mix of businesses is vital to any district. That’s why I’m excited to see Bedford Square rise, just around the corner from Main Street. In addition to retail, there will be apartments and offices. Elm Street and Church Lane will come alive.

And what’s on Church Lane? The Spotted Horse.

Why haven’t I mentioned it before? It’s exactly the casual, let’s-meet-and-chill restaurant I’ve lamented the loss of since mentioning Town Squire in the opening paragraph.

But if you’re like me, you don’t think of The Spotted Horse as “downtown.” It didn’t come to mind while you were reading this entire column. In our mental maps, Church Lane is still separate from downtown.

Once Bedford Square is completed, it will finally be equal.

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