As the Westport Inn bites the dust, and a new college football season looms, longtime “06880” reader and amateur historian Fred Cantor suggests a confluence of those 2 events for our Friday Flashback.
Fred found this fascinating ad from the October 3, 1960 Yale Daily News:

At that time the Yale football team attracted large crowds — including folks who drove up from the tri-state area.
Owners of Westport’s then brand-new “motor hotel” figured they could snag some of the traffic, on the way to and from New Haven.

Back view of the New Englander Motor Hotel. In the front, the Post Road is not visible; beyond it is an artist’s rendition of Long Island Sound, actually a couple of miles south.
The copywriter was right about both bowling (the Backiels’ Westport Lanes was a few hundred yards down the Post Road; it’s now the site of the Bevmax shopping center) and skating (a rink was nearby in the opposite direction, though it was hardly “beautiful”; it remains today, as the indoor Westport Tennis Club, behind the new Tacombi restaurant).
I’m pretty sure though that the lounge was not “famous.”
And — even allowing for less traffic then than now on the “Connecticut Turnpike” (I-95) — there’s no way to make it from Westport to the Yale Bowl in 20 minutes.
As for “Dine well!”: Westport had its share of restaurants.
Among them, right next door to the New Englander was Bob Charpentier’s Bantam:

What a menu: Steaks. Chops. Lobster. And frogs [sic] legs!

Bantam Restaurant.
A few years later, Bantam became Chubby Lane’s — Westport’s first $1 hamburger place.
Bob Charpentier opened a butcher shop across the street. He supplied the great meat for those great Chubby’s burgers.
Charpentier’s Butcher Shop is now Border Grille.
And the Bantam/Chubby Lane’s/Ocean House (and other restaurants)?
Today it’s the site of Willows Pediatrics.
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