Map Quest

A decade or so ago, RTM member and pilot Irwin Donenfeld invited me on a flight over Westport in his small plane.

We took off from Sikorsky Airport.  Banking over Bridgeport and flying west, a remarkable thing happened:  I “saw” the border separating the city from Fairfield.  Because of suburban zoning regulations, the demarcation — in foliage, home sizes and density — was as clear from the air as if a line was drawn on a map.

A couple of minutes later, approaching Westport, the same thing happened.  This time was even more dramatic.  2,000 feet in the sky, I felt as if I was seeing a map.

Google Maps has brought satellite views to laptops and cellphones.  But I’ve never forgotten the images of that flight.

Westport, looking east over the Post Road bridge. Note the small size of downtown; the surprising amount of foliage -- and the proximity of the Saugatuck/King's Highway School athletic complex (lower right) to downtown.

I thought about that experience recently, when I read about the Westport Historical Society’s upcoming exhibits:  “Zoom in on Westport” and “Putting Westport on the Map.”  Opening this Sunday (Oct. 3, 3-5 p.m.), they combine 2 fascinating elements of Westport life:  aerial views, and the changing map of our town.

“Zoom In” features bird’s-eye photos taken by photographer Larry Untermeyer.  If they’re anything like what I saw on my flight, they’ll open your eyes to a Westport far different from the one you thought you knew.

Compo Beach, for example, does not lie directly opposite Long Island; it juts out at a sharp angle.  And the Post Road, that straight shot through town from Fairfield to Norwalk?  It twists and turns every few yards.

The Sherwood Mill Pond covers more area than we imagine -- and its contours are more irregular than we think.

The 2nd exhibit includes maps from long before Westport’s official incorporation, and a “humorous” town map from 1921.

The WHS’ iconic 1878 map — listing every downtown harness maker, coal merchant and dry goods purveyor, plus the homes of Westporters with names like Jessup, Gorham and Treadwell — will no doubt be displayed too.  It provides a perspective on this place you’ll never get from a book or news clippings.

You may not get to fly over Westport soon.  But the Westport Historical Society will provide a grounding in our town’s history you won’t forget.

(The Westport Historical Society’s exhibits run through January 8.  For more information click here or email

13 responses to “Map Quest

  1. Thanks for that great publicity for the WHS Maps exhibit.

    Katie Chase

  2. Larry Perlstein

    Dan, did you see me waving at you? 🙂

  3. The Dude Abides

    I have not done a study but inferences have tended me to believe that, while the density of population may have increased over the past 50 years I have been associated with this town, the population has not increased dramatically. Is this correct??

  4. The Dude Abides

    Interesting. More houses, closer together but yet less people. And, no doubt, more commercial structures. I wonder what Principal Dolig’s Swede would make of that?

  5. Wendy Crowther

    I love that one of the aerial photos you displayed is of the Sherwood Mill Pond. Though it’s truly one of our great Westport assets, it’s easy to overlook its beauty and historic prominence as we zoom past it on Hillspoint Rd. or the turnpike.

    In the lower left portion of the photo, I hope readers will notice the prominent white building, topped by a green roof, visible on the pond’s shoreline. It’s the iconic Allen’s Clam House restaurant. Though the restaurant was torn down in 2004, the site has been newly converted into Westport’s newest park, the Sherwood Mill Pond Preserve (the Town purchased the property in 1999). The official opening of the park will be recognized on Saturday, October 8th via a ribbon-cutting ceremony at 10:00 a.m.

    Though the aerial view is impressive, come down and see the pond from a landlubber’s perspective too. I suspect Capt’n Allen is smiling knowing that the new park will enable generations of Westporters to continue to enjoy his stunning view of the pond, nearly a hundred years after his clam shack first opened its doors.

  6. Dude, when we were kids in the 50s and at Staples in the mid-60s the population was 20-25,000. We were part of the population boom that occured between the late 1940s and early 60s when the nature of the town changed completely. Medium-sized homes for many big middle class families. My late father used to say that around 1960, out of a population of around 20,000 there were 2,000 who commuted to NYC to work. By the late 80s, he claimed, the population was nearing 30,000 but the number of NYC commuters remained stuck at 2,000. The town was molting again.

    • Not sure how reliable this statistic is, but I have heard that more people now commute into Westport than commute out of it.

    • The Dude Abides

      I am amazed that only 10% commuted to NYC in our heyday, Tommy. Thought it would be more. I have also heard Professor Woog’s supposition: there are more commuting TO Westport now than commute FROM Westport. I still find it interesting that the population, with such changes, has remained the same or lessened. To my sophomoric understanding, it is movement to an eventual aristocratic Westport with huge estates encompassing most of the township.

  7. From Wiki for what it’s worth. It appears from these figures that the population has declined slightly since 1970.

    of Westport[1]
    1840 1,803
    1850 2,651
    1860 3,293
    1870 3,361
    1880 3,477
    1890 3,715
    1900 4,017
    1910 4,259
    1920 5,114
    1930 6,073
    1940 8,258
    1950 11,667
    1960 20,955
    1970 27,318
    1980 25,290
    1990 24,410
    2000 25,749
    2009 26,799