The covers offer clues to what’s inside.
On the front is a photo of the handsome stone building that is now Massi Co.
The back shows Westport’s classic Town Hall.
If you’ve been here a while, you know the relationship. The Post Road restaurant on the front is our original Town Hall. (The current one is the repurposed Bedford Elementary School.)
Westport’s original Town Hall.
The images are from “Westport Connecticut: The Old and New Historical Accounts.”
Bob Weingarten’s 234-page book — plus 4 appendices, and an exhaustive index — is the first history of this place since Woody Klein’s “Westport Connecticut: The Story of a New England Town’s Rise to Prominence” in 2000.
Heavy on Greens Farms (the author’s neighborhood since 2002) and on historic homes (his passion), it also features stories about Longshore, the Minute Man Monument, road names (spoiler alert: Cross Highway comes from its “crossing” of the Eleven O’Clock Roads) and more.
“Stories” is the right term. The book includes 37 “articles,” many of them originally written by Weingarten for Greens Farms Living magazine, and other publications like Westport Magazine. (He is a frequent contributor to “06880,” too.)
Weingarten is not an architectural historian by training. He has a master’s degree in electrical engineering, and spent 30 years in software development.
But after moving more than 2 decades ago into an 1805 barn, he devotes hours each day to research.
Old homes are of particular interest. Weingarten has obtained 359 historic plaques; curated 5 exhibits for the Westport Historical Society; served as house historian for the WHS (and now the Westport Museum for History & Culture), and spent 10 years on the Historic District Commission.
Bob Weingarten, with one of his historic home plaques. The Simon Couch Chaise House is on Morningside Drive.
This book grew out of all that. It’s an important complement to Klein’s work, and George Penfield Jennings’ exhaustive “Green’s Farms, Connecticut: The Old West Parish of Fairfield,” published in 1933.
(About that apostrophe: Weingarten addresses the centuries-old debate about the proper punctuation of Greens/Green’s Farms in depth. Spoiler alert: He prefers “Green’s,” but concludes, “Your call!”)
His exhaustive look at historic homes — illustrated with plenty of photos — ranges into areas like barn conversions (“there were a lot more than you’d imagine,” he says), and the Underground Railroad. (Spoiler alert: Though Westporters helped enslaved people on their journey north, no Westport homes have been “officially certified” as stops on the network of secret routes.)
Have you wondered about Westport’s oldest houses? Weingarten writes about them (and includes photos): 187 Long Lots Road (circa 1683), 46 Kings Highway South, 28 Compo Road North, 81 Clapboard Hill Road and 41 Kings Highway North.
(Speaking of Long Lots, spoiler alert: The term comes from land grants that were just 50 to 875 feet wide, but 10 miles long.)
The oldest home in Westport is on Long Lots Road, near the Fairfield line. (Photo/Larry Untermeyer)
Weingarten also discusses well-known Greens Farms residents, like Rodney Dangerfield, Gene Tierney and Robert Ludlum; modern topics like solar panels, and the “changing streetscape” of structures that have been moved, like the Kemper Gunn House (from Church Lane across Elm Street, to its current incarnation as Serena & Lily), and nearby Spotted Horse Tavern.
He also mentions the Red Barn restaurant, a historic structure on the other side of town from Greens Farms. It was in the news recently (after the book was published) because its owner, the Westport Weston Family YMCA, plans to build an ice skating rink on the site.
So is our historic architectural character — of homes, the Red Barn and more — in jeopardy?
Despite his deep love for old homes, Weingarten takes a measured tone: “We need to carefully study any proposal (for change) from both a preservation point of view and a property owner’s point of view. Not an easy task.”
“Westport Connecticut: The Old and New Historical Accounts” will launch officially with an event at the Westport Book Shop on July 8 (6 p.m.). There will also be a signing at MoCA\CT, at a date to be announced. For more information, and to purchase, email rwmailbox@aol.com.
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Bob is a master of reading old deed’s, among his many other talents. Love the new book.
Thanks BW for all you do !
I have the original deeds framed from my grandfather’s Old Road farmhouse and the 7.2 acres he purchased on the Post Road in 1917. The Old Road property which I think was 4 acres he brought for $600, and the Post Road property for one dollar down, and a $5,000 dollar mortgage at 5% and he paid it off in 1927. When he first purchased the Post Road property he erected gigantic advertising billboards on the part of the property where the bowling alley eventually was built. Somewhere I have a picture and the billboards can be seen in the background and they’re huge like maybe the height of a telephone pole. I could go on and on, but maybe later I’ll comment again.
This comment is called “ The Road that disappeared.” I have a photo of my father riding his horse into the driveway on the farmhouse on Old Road. Old Road is perpendicular, but you could see the driveway seems to cross over and go down to the Post Rd. Well, there was a dirt road and a sign saying “Private Road, and it was there for maybe 50 years. The people who bought the house across from the farmhouse covered up the road and it’s a lawn now. I wonder if legally these two homeowners could petition to open that road up again, and wouldn’t that make their property more valuable? I’m sure those who lived in the neighborhood remember that dirt road and used it to access the Post Road.
Bob Weingarten has done so much over many years to address historic issues and preserve or enhance historic structures and spaces. His book is one more chapter in Bob’s personal book as to his many accomplishments for Westport, indeed Connecticut.
Thank you, Bob
I can’t wait to add this one you our library! We moved from California to New England BECAUSE of its history and, back in 1990, we had a real sense that this was the case. But today, it’s bitterly not so much…The Red Barn: an ice rink? How very sad.. I feel the sheer essence within the walls of our circa 1730 Banks Tavern, here in Weston, shivering in terror.
Looking forward to adding Bob’s book to my library of all things Westport!
I’m live in a historical house in Wesoton – 1763 called the Simon Couch house. Can there be two? Seems strange.
Sarah Barrington
There are all sorts of history errors..which is the fun of it!! For instance, the Nash house on the post road and Kings Highway isn’t the original Nash homestead. The original home was much more modest. I love thinking about what went on in the minds of owners and historic researchers from years ago. Probably the case with Couch a very early name!
The photo is for the 1805 Simon Couch Chaise house. The owner could have been a grandchild of the Simon who owned your house.
During Colonial times, and even today, first names were reused generation after generations. In some cases, families appended Jr. and Sr. until the death of Sr and then the Jr was omitted.
If you read my new book of Westport CT Historical Accounts of 1639-2025, you will understand why Simon Couch was the owner of my house, i.e. a barn in 1805. There is a article (chapter) devoted to how to determine when a house was built which uses my converted barn as the sample.
Definitely a must-read! I’m curious if he unveils new info about a particular “dead” brook and more we speculate about regarding Westport.