It’s time for another installment of our “06880” Question Box.
This is the feature in which I try to answer readers’ questions.
I don’t have all the answers. But our readers — in their collective wisdom — might.
Please chime in with any additional information. Click “Comments” below.
This edition is short on quantity. But the quality of the questions is high.
As always: If you have a question for our box, email 06880blog@gmail.com.
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The large cylindrical hill not far from the small Winslow Park parking area on Compo Road North has always intrigued me.
It seems too perfectly symmetrical to be natural. And it looks so much different than the surrounding area. There are no other mounds like it anywhere. Is it man-made? If so, why? (Anonymous)
That’s a fantastic question. And — despite living a few yards away from Winslow Park, and walking there often (without a dog) — it’s one I’ve never even thought of.
Now that you mention it: You’re right. That hill (a longtime favorite spot for teenagers to drink, get high and hook up) definitely looks out of place.

Winslow Park mound/hill. (Photo/Dan Woog)
Could it have been built by indigenous people, long before Europeans arrived?
Perhaps it was constructed when the Winslow family owned a mansion — one of the most luxurious homes in town — at the corner of North Compo and the Post Road (State Street)?
Or maybe it was part of the Westport Sanitarium, which took over the estate?
I have no idea. But I’ll never again walk past without wondering what it is, and why it’s there.
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Why do they take the flags down after Labor Day? It’s kind of sad without them flapping in the breeze. (Deborah Baker)
“They” — aka town workers — remove the flags because of possible inclement weather. (Not just snow — possible hurricanes or nor’easters.)
It might also be a cost-saving measure, to extend the lives of the flags. They do look great. But there sure are a lot of them.
Here’s something to look forward to, though: October 24.
It’s UN Day. And, for one of 2 days each year (the other is jUNe Day), flags of dozens of nations will fly proudly on the Ruth Steinkraus Cohen Bridge.

Long may they wave. Or at least, every spring and summer. (Photo/Lauri Weiser)
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What can a neighborhood or residents on a common street do about a neighbor that neglects the upkeep of their home and property?
The neighbor’s house needs to be painted. Their back yard (which can be seen from the street) is completely overgrown. Their side yard is a dump heap, and their bushes grow out into the road. It has a negative impact on all our properties.
Can the town enforce homeowner upkeep? How do we get this fixed? (KR)
The town of Westport has a Blight Prevention Board. It’s made up of private citizens and a Building Department official. They listen to residents’ concerns, and take their work very seriously. Click here to read an in-depth story on them, from the “06880” archives.
Sometimes, there is an underlying issue with a house in that condition. The Department of Human Services may be able to assist residents in need.

These dilapidated buildings on Post Road West have since been demolished.
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I read a long time ago, that the Native people ate a lot of the oysters from the sound nearby. These mounds, there were others, are made ode of their shells and other refuse.
I’ve always thought that mound in Winslow park was a drumlin. “A drumlin is an elongated, oval-shaped hill formed beneath a moving glacier, primarily composed of glacial till (sediment deposited by the glacier), and shaped by the ice flow,”
Although I could be wrong…
The American flags on the bridge: Originally, they were only flown on National holidays — 4th of July etc. But after 9/11 when we invaded Afghanistan and then Iraq, then First Selectwoman Diane Farrell ordered them to fly “until the troops come home.” In my opinion, seeing them every day diminishes their significance.
Here is my husband’s take on the hill at Winslow Park which would also include the one at the Baron’s which is very very steep … He believes it goes all the way back to when the glaciers melted …. They formed drip castles through holes under the ice as it melted ….
Great timely question this morning.
The answer is in the Compo House and Sanitarium.
Previously both in Barrons North, the Compo House and the sanitarium along with other buildings were removed and actually burned in the early 70’s and their remains created the hill, a.k.a. the landfill/look out spot.
Thanks to the Nicole of the Westport Museum for a in depth tour and look back at the history of the park and land.
PEL
The hill at Winslow. I went there a lot over many years with my dog Norman and never thought about it until you mentioned it here. My mind jumped to “graves?” (I know, my friends lovingly call me “Wednesday”.) I like Sue’s explanation 👌
I was told by a reputable source that the hill in Winslow Park was created when the land was purchased by those who started the Sanitarium. When the Sanitarium was built/enlarged to include buildings located behind the Manor House formerly owned by Winslow, the hill was created by the large amount of dirt that was excavated to create the foundations and presumably the basements of the new buildings. Supposedly, it was a created purposely as a landscaping feature. Sanitariums were trying to provide scenic vistas and therapeutic settings.
Originally, some people theorized that the hill may have predated the sanitarium and that it was an “Indian Mound.” Somewhere along the line, that theory was abandoned or disproved.
I’ve heard the same thing, Wendy. There’s been speculation that Olmsted may have been the sanitarium’s landscape architect. As it happens, he was hired to create the original landscape plan for the Hartford Hospital for the Insane.