This month, Staples students gear up for the next round of SATs and ACTs. That’s not rare; standardized tests are one of the many rites of passage through high school life.

But why should the joys of test-taking be limited to teenagers? How about a “How Well Do You Know Westport Quiz,” for all the rest of us?

You can work in teams. But no Googling allowed. The answers are at the end.

1) If you were in Westport in the early 1950s, your phone number began with the number 2. In the middle of the decade, it was lengthened to CA7. What did CA stand for?

2) Le Penguin, in Sconset Square, is one of Westport’s popular new restaurants. But there was another Penguin, years ago. What was it, and where was it located?

3) Speaking of Sconset Square, why was its name changed from the original Sherwood Square?

4) Speaking of Sherwood Square, what did Francis, Franklin and Frederick Sherwood have in common?

5) When Westport was incorporated in 1835 as a separate town — apart from Norwalk, Fairfield and Weston — there was some debate about what to call it. What other name was considered, and why was it rejected?

6) An ongoing debate involves the punctuation of Greens Farms. Should there be an apostrophe? If so, should it be Green’s Farms (for Green, one of the original Bankside Farmers, who founded the area) or Greens’ Farms (for the entire Green family)? However, no one ever talks about the improper punctuation of Hillspoint Road. What should it be?

7) What is the connection between Staples High School and the Wilbur Cross Parkway (the northern extension of the Merritt Parkway)?

8) If I gave you directions to Fort Apache — but told you not to leave Westport — where would you go?

9) You probably never thought of this, but why do we call it Roseville Road?

10) Speaking of standardized tests — as I did in the first paragraph — in the 1950s, Staples High was the first school in the state to offer a certain academic course. What was it?


1) CA in phone numbers stood for “Capital.” Westporters living near the Fairfield line had CL9 numbers, for “Clearwater.”

2) The Penguin was a restaurant/nightclub, with a nautical theme, on Hillspoint Road just over the railroad tracks. The Edgewater Commons condos are there now. It was an impressive building, which in its first incarnation as a jazz club/speakeasy, was supposedly the first air-conditioned night spot between New York and Boston. In its final days it was a rundown apartment building, with the reputation (at least among Westport youth) of being a brothel. Although we used an earthier name.

3) Sconset Square — the small shopping center on Myrtle Avenue — was originally called Sherwood Square to honor one of Westport’s most famous 19th-century families. The current name is meant to evoke Cape Cod, for reasons known only to its owner.

4) Francis, Franklin and Frederick Sherwood were triplets. The youngest of 10 children, they went to sea in 1826 — age 16 — and all became noted captains.

5) At its incorporation in 1835, Westport might very well have been called Saugatuck. However, a state legislator objected. He worried his colleagues in Hartford might call him “the man from Succotash.”

6) Hillspoint Road is actually Hill’s Point. It’s not named for the hill that descends from the site of the old Penguin (see answers No. 2). Apparently, someone named Hill once owned land in the area. I don’t know, however, where his point was.

7) In 1886, Wilbur Cross became the second principal of Staples High School. He was only 22 years old — but “principal” at that time meant “principal teacher.” There was only one other one in the building — I wonder what he or she was called. Over 40 years later, after a distinguished career as a Yale University English professor, Wilbur Cross was elected governor of Connecticut. The new parkway was named in his honor.

8) Fort Apache was the nickname given to what is formally called the Willows Medical Center on Kings Highway North, at the corner of Wilton Road. The modern — as in, 1960s — design reminded local residents of the Arizona Indian-fighting camp.

9) Once upon a time, Morris Ketchum owned much of the land between his Hockanum estate on Cross Highway, and the road we now call Roseville. His Irish gardeners planted roses all around the area. Ketchum also owned property extending north, nearly to Lyons Plains. Once a week, he opened his grounds to Westporters, for picnics and such.

10) Staples was the first high school in Connecticut to offer Advanced Placement courses. Look what we’ve started.

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