It’s election season. You can tell, because every traffic island, front yard and square inch of Westport that does not already have a sign advertising leaf blowing, fundraisers or a tag sale is filled with signs touting candidates for public office.

I have never known anyone who said, “I am voting for Mr. X (or Ms. Y) because he (or she) has the coolest sign!” In fact, every political sign looks like every other one — and every year they all look alike.

Perhaps something subtle is at work here. Maybe voters enter the polling booth — er, stand behind the polling desks — and say, “I am voting for Ms. Z because I know her name.” Or perhaps this is a nuclear arms race, political sign style, in which no office-seeker wants to be out-placarded by the other guy (or gal). I realize, as we stand on the precipice of Armageddon with North Korea, that a nuclear bomb is not the wisest analogy to make, but it might be my last one ever so I’ll blast away.

So if you are not going to pull the lever — I mean, fill in the circle — based on road signs, how you gonna choose?

Fortunately, Westport is a small town. You can meet most candidates here and there: the train station, neighborhood events, and the perennial favorite, the dump — that is, “transfer station.”

Wednesday, Oct. 18 (7:30 p.m., Westport Country Playhouse) is a special evening. Westport Front Porch and Westport Moms — two very active Facebook groups that have seen some pretty harsh political posts dynamite the usual civil discourse about where to buy the best baby stroller, arugula and yoga pants — are co-presenting a meet-and-greet.

First selectman candidates will give brief (we hope) speeches about their goals and visions. Candidates for all other municipal offices will wear name tags. They’ll be available for questions, comments and (hopefully) intense but respectful debate.

This is a perfect opportunity to corner — sorry, politely question — the men and women seeking to serve our town about how, exactly, they plan to do it. “Serve” is the operative word. First selectman is a paid position. Second and third selectmen receive teeny-tiny pittances. Every other elected position is volunteer. When you think about how much time, energy and agita that entails, you may not want to vote for any of them — because it must mean they’re all crazy.

So what can you talk about? How can you learn candidates’ qualifications, beyond the fact that they have yard signs? Here are a few conversation starters.

Ask the first selectman candidates about the pressing issues in Westport: traffic. Redevelopment of downtown and Saugatuck (including the Transit Oriented Design plans for the area around the railroad station). Infrastructure — including dredging of the Saugatuck River, and what to do about the William Cribari/Bridge Street Bridge.

Taxes and pension benefits are huge too. Some of this is out of our first selectman’s hands. Some depends on whatever happens in Hartford, which right now is about as predictable as the next move of North Korea’s “Rocket Man.” But it’s worth asking the men (and woman) seeking our chief executive’s post what they will do when state legislators pull the plug on funding, or when the next municipal employees’ contracts come up for negotiation.

Compo Beach is not part of the first selectman’s portfolio — not directly, anyway. But ask the candidates about their relationship with the Parks and Recreation Department. Find out what type of people they’d appoint to the Parks and Rec Commission; how he or she would work with them, and what direction they’d give to members.

Other offices are on the ballot too. The Board of Education is responsible for a huge chunk of Westport’s budget. Where should the portion not dedicated to salaries be directed? How can Westport maintain its “lighthouse” standing at a time of fiscal uncertainty in Hartford, yet increasing demands for standardized testing and curriculums? What can we do to help students in our little bubble become engaged, active citizens of the world?

The Board of Finance is also key. All of the challenges identified above — for the selectmen and Board of Education members — ultimately funnel through the money men (and women). Asking hard questions about priorities, solutions and hard choices — and demanding concrete answers — is crucial.

I could spend an entire column on the Planning and Zoning Commission. No body is more integral to the future of Westport. The entire character, livability and future of our town rests on their votes.

Will you be there to meet the candidates on Oct. 18? There should be no question about it.

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