The other day, alert “06880” reader Amy Leonard discovered an August 8, 1949 Life magazine. The cover promised an inside look into “Fairfield County: Country Home of Smart New Yorkers.”
Amy asked if I’d be interested. She knows me well.
Just a couple of years before Westport roared into a post-war baby boom ‘burb, Life portrayed our town — and the rest of the county — as a place most readers could only aspire to.
The country’s most popular magazine located us “between the sailboat-dotted waters of Long Island Sound and the woodsy border of New York State.” Our “scalloped shore line” offered “hundreds of miles of valuable waterfront property.”
The “electrified New Haven Railroad and high-speed Merritt Parkway” provided swift access to New York City. Our “rolling hills and leisurely life” attracted well-to-do, already successful commuters.
“Their existence is not utopian,” Life warned. Commuters’ days revolved around the 7:43 a.m. train to New York, and the 5:16 p.m. back. Taxes were high, “and servants expensive.”
But, the story continued, “for the New Yorkers who can, or think they can, afford a country home, Fairfield County is probably the best — and the newly fashionable — place to have it.”
They could, for example, pay $140 a year beyond the regular train fare. That got them a seat in the railroad club car: “an exclusive, air-conditioned arrangement for wealthy commuters who prefer not to ride in coaches.”
Not everyone took the 7:43, of course. “Idea people” — artists and authors whose commuting schedule was not as rigorous as businessmen — had long lived here.
In fact, Life said, “there are probably more professional artists within a 25-mile radius of Westport than in any comparable spot in the U.S.” Just 4 years old, the Westport Artists Club already boasted 148 members.

This shows Westport artist Stevan Dohanos — a famed illustrator for Life’s competitor, the Saturday Evening Post — drawing a classic New England church in Easton.
The Life story ended with a few aspirational photos: a painted split rail fence, station wagon, old window pane and beagle, among them.
Described as “some of the items which commuters consider essential to a happy life in Fairfield County,” they distinguished “the transplanted New Yorker who has fled from the sameness of apartment life, and is now making his country place as similar to the one next door as he can.”
Life ceased weekly publication in 1972. What would a current story on Westport say and show?
Click “Comments,” to add your 2016 view.

The caption reads: “New arrival in Westport is James Donovan, a wealthy young (34) executive who bought his home two years ago. He is one of many such newcomers.” (No mention of his wife or kids, also in the picture.)
sigh…
The Westport Country Playhouse presented more than plays. In the summer of 1957 I had finished my freshman year of college and was living with my parents in Westport and working for a company in Norwalk that made transformers. My mother said, “Robert Frost will be appearing at the Playhouse on Wednesday, Take the afternoon off from work and come with me. ” My boss gave me the half day vacation (unpaid) and I went. It was just wonderful. I can still hear Frost saying
“One could do worse than be a swinger of birches. ”
The Life article speaks of the large number of commercial artists living in Westport in the late 1940’s. One wonders if even a small number could live there today when the average house sells for 1.1 million dollars. I wonder where artists in Connecticut are now–most likely in Bridgeport.
ADW Staples 1956
I nearly jumped at the bar car, oops, I mean Club Car picture. At first I thought it might include my grandfather. Both sides of my family go back to the 1600’s in Connecticut but by the 1930 only my Dad’s family was still in Connecticut. My mother’s family was in the process of moving back to Connecticut from Florida during the depression. Just this weekend I was rereading their letters deciding which Connecticut town they would live in.
My grandfather had secured a job with the Irving Trust in NYC. It was fascinating to read the discussion of Greenwich, Darien, Norwalk or Westport. The answer was Westport. They traded houses with someone who wanted to move south as financing was not available during the depression. Fascinating article. I remember a big influx of people in the early to mid 1950’s
Your memory is accurate. From 1950 to 1960 the population of Westport increased by about 80%.
Excellent, Dan
My father rode the club car for years. It was called the Southport car and was restricted to riders from the Fairfield Southport and Greens Farms stations only.
Yep, this a fantastic and fun issue on Westport and the whole Fairfield County draw from NYC–those “smart New Yorkers!” .( Inside it also features the famous Jackson Pollack spread!) I have used if for for many an exhibit in the region.
The Westport “Idea” was burgeoning and being marketed as such in the early 1930s too. Dan, I will send you a follow up article I recently found on this .
The photo of Steven Dohanos painting a Saturday Evening Post cover must be a publicity shot. No one paints a picture in a position like that !
More interesting is message board he adds to the painting. That guy is standing where he needs him to paint him in proportion to the board he’s adding. That’s actually a little sad because I always thought those pictures were exact drawings. Guess not!
James Donovan is sitting on the lawn in front of the main house at Burritt’s Landing before the estate, formerly owned (as the rumor goes) by the mistress of one of the robber baron’s, ( I think JP Morgan) was broken up into 16 lots by Attorney Alan Senie when he developed the property in the late 1960’s.
Ken
J. Graves is not correct about the stops made by the Southport Club Car:
It also stopped in Westport. My gandfather J.P. Bradley boarded the Club Car daily for more than 25 years at the Wspt station and returned there after work. I rode in it myself many times as a little girl, taken to NYC by my mother to see friends & shop. Families of the Club Car members were welcome on the car as passengers.
And, glad to see that dear friend Peter Barlow is still alive & kicking! 😌
This makes me think of the classic “Mr. Blandings Builds His Dream House.” Cary Grant and Myrna Loy. 1948.
What about the Twilight zone “next stop Westport” haha
Here you go! https://06880danwoog.com/2009/10/05/last-stop-willoughby/
The caption might read: “Marion Donovan, inventor of the forerunner of the disposable diaper