Tag Archives: Peter Jennings

Who Is Buried At Burying Hill?

Posted on October 23, 2025 | 9 comments

Descendants of the Jennings and Couch families gathered at Burying Hill Beach on Sunday to dedicate one of 4 new monuments extends the Jennings Trail.

What is now named Burying Hill Beach was referred to over 200 years as “The Couch Family Burial Ground/ Couch Burial Hill.” Purchased by Simon Couch around 1660, what he called “his beautiful hill overlooking the sea” was the only burial ground in Green’s Farms, until the West Parish developed its own in 1725.

Couch Burial Hill most likely holds the remains of many colonial settlers, including members of the Jennings, Couch and other local families. All were neighbors and relatives.

Members of the Jennings and Couch families gathered for Sunday’s celebration. (Photo/Emily Jennings)

Francis Andrews, a founder of Hartford, early settler of Fairfield (and Simon Couch’s father -in-law) is also said to be buried there.

The town of Westport acquired the property in 1893, after claiming that the last headstone had gone missing. The name “Couch Burial Hill” was changed to “Burying Hill Beach.” It was the first shoreline park to be designated and approved as a recreation area by the State Legislature.

The Jennings Trail Committee worked for 2 years to research, organize and fund the 4 additional monuments. Jennings Trail Committee chair Peter Jennings joined local historians Morley Boyd, Wendy Crowther, Robert Liftig and Bob Weingarten to complete this first phase of the project.

Peter Jennings and Inez Liftig install the plaque. (Photo/Bob Liftig)

Jennings Trail is a self-guided tour of 2 dozen historic Westport sites, each marked with a plaque. It was conceived in 1974, as part of Westport’s part of the US bicentennial.

The Trail is named for Bessie Jennings, whose family first settled in this area around 1650. She guided 3rd graders along it for many years.

Now under the stewardship of the Westport Historic District Commission, it is maintained — at his own expense — by Peter Jennings, an 11th-generation Westporter and Bessie Jennings’ cousin.

(For more information on Burying Hill Beach, click here.)

(“06880” reports regularly on today’s Westport news — and occasionally looks back. If you enjoy learning about our history, please click here to support our work. Thank you!)

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Posted in Beach, History

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Unsung Hero #338

Posted on June 12, 2024 | 24 comments

Longtime local historian Bob Weingarten writes:

Peter Jennings is an 11th-generation Westporter. His family settled in this area around 1650.

For the past 23 years Peter has quietly maintained Jennings Trail, Westport’s network of roadside historic markers.

And he’s done it at his own cost.

Jennings Trail is named in honor of Peter’s cousin, beloved educator and well- known authority on Westport history, Bessie Jennings.

Originally conceived in 1974 as part of Westport’s plans to celebrate the Bicentennial, the Trail was initiated by the Westport Historical Society in collaboration with the Westport Young Woman’s League.

One of the plaques on Jennings Trail marks the Elmstead Lane home where Bessie Jennings was born, and died.

23 markers were installed at historic locations throughout Westport. They are made of bronze, mounted on stone plinths, and contain brief narrative descriptions that describe the significance of each site. Jennings Trail is now under the stewardship of the Westport Historic District Commission.

As it has been nearly 50 years since the markers were first installed, maintenance is necessary. On a recent weekend, Peter was spotted at Machamux Park off Greens Farms Road – site of our community’s very first meeting house.

Peter Jennings, rebuilding the Machamux marker base …

He carefully rebuilt the masonry base and reinstalled the bronze marker for the park’s Jennings Trail marker.

… and reinstalling the marker …

Meanwhile Peter, together with a small group of other local historians, is currently planning the first major expansion of Jennings Trail since the Bicentennial.

The group knows that a number of Westport’s most historic sites remain hidden in plain sight. Initially, 4 new markers will be installed. Each has a fascinating story to tell.

In the meantime: Thank you, Peter, for keeping Westport’s past alive.

(Unsung Hero is a weekly “06880” feature. To nominate a hero, email 06880blog@gmail.com. To support our work, please click here. Thank you!)

… and inspecting a site for a new marker. (Photos/Bob Weingarten)

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Posted in History, Looking back, Unsung Heroes

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Roundup: General Judah’s Grave, 246 Hillspoint Road

Posted on April 21, 2024 | 5 comments

After 158 years, Henry Moses Judah has a headstone.

The Westporter was the last Civil War general in the nation with an unmarked grave.

For 158 years, his remains lay in the town cemetery at the corner of Wilton Road and Kings Highway North. He shared his grave with several dozen others — including his father, Rev. Henry Judah, and mother Mary Jane. — in a tomb marked for Ozias Marvin.

The Judah family was among the first Jewish residents of Westport (then part of Norwalk). Michael moved from New York City in 1742 because of anti-Semitism. He was a merchant trader, specializing in corn shipped to the West Indies.

His son Henry became an Episcopal minister. (There was intermarriage in the family with non-Jews, including the Jesup family.)

Rev. Judah’s Henry Moses Judah fought in both the Mexican-American and Civil Wars. He died at 44 less than a year after the Civil War ended, apparently of alcoholism.

The Judas family owned an estate in Saugatuck, which was named for them. Over the years, Judah’s Point morphed into Judy’s Point.

Peter Jennings — an 11th generation Westporter, and the author of a book on local cemeteries — helped give General Judah his headstone. He also cleared brush from the site, before the headstone’s installation.

It was paid for by the US Department of Veterans Affairs. Installation costs were covered by Shrouded Veterans. The non-profit identifies, marks and restores 19th-century graves.

Meanwhile, plenty of restoration is needed for the graveyard at one of Westport’s most visible corners.

Grayson Braun, chair of the Westport Historic District, notes with chagrin that debris has been dumped throughout the cemetery.

Before the headstone was laid, she caught a neighbor dumping yard waste there.

(Want to learn more about this, and other Westport’s cemeteries? Click here.)

Brigadier General Henry Moses Judah’s tomb …

… and headstone. (Photos/Grayson Braun)

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The end is near for 246 Hillspoint Road.

The tiny wooden shotgun house has stood — if not tall, then proudly — as all its neighbors were torn down and replaced by far larger homes.

The 2-bedroom, 1-bath, 695-square foot house sold in 2022 for $1.5 million.

A demolition sign hangs on the side.

Another in front says “Luxury Homes.”

And though this is not luxurious — it’s just one of the last beach shacks left in Westport — we all know: This soon will be a luxury home too.

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Johanna Keyser Rossi describes today’s “Westport … Naturally” photo:

“This squirrel outfoxed the fox. He knew how to get to the bird feeder attached to the outside window at the Senior Center.

“He climbed up the wall. It was funny to watch. Then he chased  away the dove on the ledge.”

(Photo/Johanna Keyser Rossi)

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And finally … today in 1965, the New York World’s Fair opened for its 2nd (and final) season.

“06880” featured the fair in Friday’s “Flashback.” Readers added many comments.

Plenty of them referenced Disney’s “It’s a Small World After All.” They still remember it, 6 decades later.

So here, for your listening pleasure — and to bring back visual memories too — is that classic earworm.

(It’s a small world — and “06880” connects Westport with all of it. But we can’t do it without our readers’ support. Please click here to make a tax-deductible contribution. Thank you!)

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Posted in History, Looking back

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Who You Gonna Call? 15 Generations Of Westporters.

Posted on November 4, 2022 | 2 comments

Peter Jennings’ family has been here for 11 generations.

Maxx Crowley — a 4th-generation Westporter — is, by comparison, a new arrival.

For years, the 2 families’ businesses have been friendly rivals — and sometimes partners — in the property management field.

Now they’ve joined forces. A recent merger created a new firm that offers a wide range of services — leasing, maintenance, bookkeeping and more — to commercial and residential owners from Westchester to Hartford.

But they’ll still concentrate on — and be headquartered in — Westport.

SCA Crowley trucks and team outside one of their properties: the 55 Greens Farms Road office complex.

After 28 yeas with the HK Group, Jennings started his own firm, Bayberry Property Management, in 2009. He eventually serviced, and served as a broker for, 80 buildings.

SCA Crowley — the business formed by Maxx’s father Steve — recently celebrated its 40th anniversary. Steve started as a real estate broker, but soon realized that property owners wanted leaf removal, snow shoveling, landscaping, pothole fixing, painting and many other services.

COVID sparked a change in SCA’s real estate management. Homeowners moving from Manhattan and Brooklyn needed help learning about irrigation systems, hot water heaters and pools, and jobs like power-washing patios. The company — whose clients already included Playhouse Square, MoCA Westport, office buildings, medical centers and Homes with Hope facilities — expanded their residential property portfolio.

(From left): Bobby, Steve and Maxx Crowley.

SCA and Bayberry had been friendly for a while. They referred customers to each other’s services.

Now, Crowley says, their combined operations will be even more seamless.

“We’re a Swiss army knife,” Jennings adds.

The merged company will be called SCA Crowley Real Estate Services. (“Steve won the coin toss,” Maxx Crowley jokes.)

Peter Jennings

The only change, Jennings adds, is the purchase of new logowear and business cards.

The new firm’s offices will be on Kings Highway North, near Main Street. Its trucks will be at Riverside Avenue.

Though properties extend from White Plains to Hartford, it will still be a “mom-and-pop” company.

Plus other family members.

Maxx Crowley works with his siblings Bobby and Judy.  Jennings is joined by his sister Karen, daughter Katie, and sister-in-law Beth.

Both families will continue to contribute to Westport, in non-property management ways too. Steve Crowley is a longtime volunteer with many civic causes. Maxx Crowley is president of the Westport Downtown Association. Jennings is the Green’s Farms Congregational Church historian.

After 15 combined generations, the Jennings and Crowley family histories continue.

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Posted in Local business, Real estate

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