Category Archives: Real estate

Then & Now #18

No matter where in town Dave Matlow went, he found soon-to-be-demolished homes to photograph.

Now, wherever he goes, he finds their replacements.

This week, Dave’s images take us to the northeast corner of town.

It’s a neighborhood of some of Westport’s oldest homes, and split levels and Colonials built from the 1950s on.

Like the rest of town, things change. Check out these 4 roads below.

Woody Lane, October 2007 …

… and June 2026.

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Cross Highway, June 2010 …

… and June 2026.

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Silent Grove, June 2007 …

… and June 2026.

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Bayberry Lane, December 2005 …

… and June 2026.

(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

After 26 Years, A New Westport History: 1639-2025

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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“Then & Now”: #17

Dave Matlow’s photographic journey, from now-demolished homes to their replacements, continues.

Today’s images take us all over town: from Half Mile Common (off Cross Highway), to Guyer Road (off Hillspoint Road), and Narrow Rocks Road (off Compo Road South).

Half Mile Common, October 2007 …

… and June 2026.

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Also on Half Mile Common, November 2004 …

… and June 2026.

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Guyer Road, November 2004 …

… and June 2026.

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Narrow Rocks Road, January 2012 …

… and June 2026.

(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

“06880” Podcast: Rick Redniss

Rick Redniss is principal planner and former president of Redniss & Mead.

A design firm that works throughout Fairfield County, they’ve been involved in residential, commercial, retail, industrial, educational, religious, government and cultural projects, as well as waterfront, parks and open space.

Their imprint on Westport is substantial. The other day, Rick and I chatted on the Library stage. Our conversation focused on our town — including the affordable housing efforts that Rick is passionate about.

Click here or below, to learn all about a design firm’s impact on a town.

“Then & Now”: #16

This week, Dave Matlow’s photographic chronicle of Westport’s homes — those that were demolished, and the ones that replaced them — takes him to what was once called “Westfair Village.”

One of the town’s earliest post-war developments, off Bulkley Avenue North and behind Westfair Shopping Center, it’s a tight-knit neighborhood with smaller-than-Westport-average lots.

During its near-80-year history, it’s seen many generational turnovers. Today — once again — it’s filled with families with young children.

Three homes from that neighborhood are featured today. The fourth — Blue Coat Lane — is off North Avenue, near Bedford Middle School.

Hunting Lane, April 2017 …

… and June 2026.

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Westfair Drive, December 2012 …

… and June 2026.

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Dexter Road, January 2005 …

… and June 2026.

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Blue Coat Lane, February 2014 …

… and June 2026.

(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

50 Sylvan Road: Historic Home Restored, Ready For Next Century

All over town, builders and families are buying old (and some young) homes, and tearing them down.

Some were poorly constructed, and go easily. Others are more sturdy. But they too succumb to the wrecking ball.

It will take a lot to topple 50 Sylvan Road North — the 1920 Tudor Revival owned by a host of well-known people, including actor Frank Gorshin and billionaire Marc Lasry.

(Photo courtesy of MLS)

Fortunately, that won’t happen.

And not just because the walls are more than 2 feet thick.

50 Sylvan Road North, today. 

The 9-bedroom, 8 1/2-bathroom stone home, on a 3-acre lot, was bought 2 1/2 years ago by attorney Jeffrey Ment and Dr. Mary Murray, Westporters since 2000.

Sturdy construction, from 1920.

They’ve painstakingly renovated the long-neglected property, both inside and out.

Mary Murray, in her back yard.

The interior was in bad shape. The exterior — including gardens, statues and fountains that had disappeared under weeds and algae — was worse.

It’s taken time, energy, creativity and love. But now, 50 Sylvan — beckoning behind an old-style stone wall — looks much as it did when Charles Cutler designed it over 100 years ago.

If it looks a bit like other local landmarks, there’s a reason: Cutler also created the Westport Bank & Trust (Patagonia) building downtown, and Greens Farms Elementary School.

The first owner was Arthur Dare Whiteside, president of Dun & Bradstreet. Subsequent owners included a variety of artists and actors, including Gorshin — The Riddler on “Batman,” among many other notable roles.

But by the time Murray and her husband — who passed it often, on their walks from nearby Marion Road — bought it, it had fallen into disrepair.

It took them a while to figure out what to do, or even where to begin.

As landscape architects Beate Hochman and Emilio Mandujano explored, they found overgrown sculptures, rock gardens, even a pond. “It was like an architectural dig,” Murray recalls.

This sculpture and fountain was rediscovered, and restored.

Gradually, the property has been transformed. The owners have added their own touches too, like a farm building with 10 chickens and 5 ducks, and a nearby koi pond.

The chicken and duck coop, with pond in front.

Inside, Murray and Ment have restored carvings — of Latin sayings, animals and more — in nearly every room. They’ve brought old fireplaces back to life.

Intricate carvings, over one of many fireplaces.

They’ve worked on rooms that were important a century ago but are no longer needed, like the one where Whiteside’s driver could pull in and wait. He was not allowed anywhere else in the house.

It’s been a labor of love — and mystery — for the owner. “This is such a special place in Westport history,” Murray says. “I keep imagining that world, and what it was like, 100 years ago.

“Westport is a place of creativity. It’s nice to remember who we were, and still are.

“I don’t why anyone would need new construction, when they could have this.”

Mary Murray, at the rear of her home.

Another restoration at 50 Sylvan Road North.

Landscape architect Beate Hochman is responsible for much of the work on 50 Sylvan Road North. The detached garage in the back was added by a previous owner, after the home was built. (All photos/Dan Woog unless otherwise noted.)

(“06880” regularly covers Westport’s past, real estate now — and like today, their intersection. If you enjoy stories like this, please click here to support our work. Thank you!)

 

P&Z Gets First Look At Spinnaker Pre-App

What’s next for Saugatuck?

The Planning & Zoning Commission held its first hearing yesterday on the new Spinnaker project. “06880” reporter John Palmer writes:

The Planning & Zoning Commission and members of the public got their first look last night at the latest development proposal for Saugatuck since the Hamlet was rendered dead.

Representatives for Norwalk-based Spinnaker presented a pre-application –a first look at the developer’s plans, and a chance for any last-minute concerns to be discussed before a formal application is submitted.

The Architectural Review Board discusses the pre-application at their meeting tonight (Tuesday, 7:30 p.m., Town Hall Room 201; click here for materials).

“We know this property has a long and at times, frustrating history for the neighborhood,” said Matthew Edvardsen, principal at Spinnaker, who added he lives in town with his wife.

“We want this to be a project the neighborhood enjoys and is genuinely happy to be a part of.”

One view of the proposed Spinnaker development. Riverside Avenue is on the left, Charles Street on the right.

Spinnaker, which has developed properties in Norwalk, New Canaan, Darien, Fairfield and New Haven, bought 606 Riverside Avenue for $12.795 million, and 96 Franklin Street for $3.25 million. The rectangle parcel is anchored by Minute Man Cleaners.

“This is not the Hamlet,” said Adam Blank, an attorney with Wofsey, Rosen, Kweskin & Kuriansky, acting as land use counsel for Spinnaker. “We can assure you the project will comply with all town engineering standards.”

He added that the developers have already met with the Fire department, businesses and other town officials, as well as the state Department of Transportation. Spinnaker has also created a project website.

Unlike Hamlet, which involved a complicated mix of several properties, Spinnaker’s proposal calls for 175 mixed units within 1 block of property. Eighteen — or about 10 percent — would be considered affordable, less than the 20% that town regulations require for similar developments.

Seelan Pather, managing principal for Beinfield Architecture, which will handle design for the proposed development, said the intent is to create a “New England Village” that provides a walkable environment.

A view looking at Railroad Place (left) and Riverside Avenue.

Rather than providing a development with many amenities, he said the idea is to create a “symbiotic relationship” with downtown Westport, which he said would be the draw for people to visit.

“We are familiar with Westport, and we are trying to achieve some of that wonderful Westport energy that exists,” he said. “We will pay attention to detail. Needless to say we’ve done this before, and we know how to get it right.”

The parcel to be developed would be bordered by Charles and Franklin Streets, Riverside Avenue and Railroad Place.

Designers plan to preserve the historical feel of Saugatuck by retaining buildings such as the post office to provide a hint of nostalgia.

Along Charles Street and Riverside Avenue, street level buildings would be limited to 4 stories to avoid an urban “canyon effect,” and would feature townhouse-like apartments with stoops, as well as street-level retail and entertainment space.

A 5-foot setback from 13-foot sidewalks would help shield sightlines of a larger, 6-story structure that would house 2 levels of above-grade parking, and 4 levels of apartments that would surround a common plaza area for residents.

“You’d have to be on I-95 to see most of what’s going on there,” Pather said of the higher building.

A key feature of the new development, which differs from Hamlet, is 283 parking spaces. Most are on 2 levels that would be located at grade or on the second level, with entrances that would be hidden within the façade of the street level façade.

By comparison, Hamlet proposed 2 underground parking garages that would feature “stackers” employed to accommodate more vehicles. It would have also eliminated most on-street parking.

Spinnaker’s street-level parking plan.

Spinnaker’s version will provide 49 off-street parking spaces plus 10 on-street spaces on Charles Street, in addition to the 283 contained garage spaces.

According to Marissa Tarrallo, a traffic expert with AKRF, studies were done at 11 intersections in the area from March through May, collecting 3 days of turning movement counts as well as 9-day traffic recorder counts.

The project as currently planned would generate 57 more weekday morning trips, 88 more in the afternoon, and 129 more on Saturdays.

She said that Spinnaker’s development will generate about 80% fewer vehicle trips than the Hamlet would have generated, and almost no traffic delays more than 10 seconds at all intersections with Saugatuck Avenue.

Planning commissioners largely viewed the proposal positively, but several expressed concerns that the developers provide only 10 percent of affordable housing, when town regulations require 20 percent.

“It would be very difficult to approve something that is substantially lower than what we require of other developers in town,” said Bre Injeski, adding that a text amendment would likely need to be approved to allow a change in regulations.

“That would be a sticking point for me. I like that you have sufficient parking and the traffic numbers are not going to make traffic significantly worse.”

The current site of the Spinnaker property. Riverside Avenue is at the bottom of the photo; Charles Street is on the right. 

“This is a massive development in an area that is already congested,” noted Michael Calise. “We just don’t have the infrastructure.”

Chairman Paul Lebowitz said that he’d like to see more setbacks integrated into the streetscape, to allow for opportunities to enjoy the environment.

“When I go to Saugatuck it’s for the experience of the places there, like eating ice cream and sitting on a nice evening,” he said. “I’d like to see more of that integrated into the sidewalks.

“It’s night and day from what we were presented with previously. I will be drawn to the negative space that will make Charles Street look like something it hasn’t looked like in many years.”

(Since our founding in 2009, “06880” has covered Saugatuck from every angle: real estate, business, transportation, history and more. Please click here to support our work. Thank you!)

The Anchorage: Westport’s Newest Waterfront Views

If you’re like most Westporters, you figured the construction at 251-253 Riverside Avenue — at the foot of Sylvan Lane, on the left just before JR’s Deli heading toward I-95 — had something to do with the nondescript office building nearby. You didn’t give it a second glance.

The next time you drive past, you will.

Last week, Christine Finch Oleynick showed the finished product to the world. Well, to at least a few dozen very interested fellow realtors, and potential renters.

The renovation of a former office building flew way under the radar. It’s now 8 apartments — 2 and 3- bedrooms, right on the Saugatuck River.

The Anchorage (right) hugs the Saugatuck River.

Six are market rate: $10,500 to $12,500 a month (unfurnished). The other 2 are deemed affordable, according to state formulas.

As Westport debates large apartment complexes — some planned, some already under construction — at sites like the train station, Hiawatha Lane and Post Road West, smaller ones are cropping up all around town.

Think of the new units near Pizza Lyfe and Lyfe Café, for example.

But it’s doubtful any have the river views of “The Anchorage at Saugatuck.”

The view from the kitchen (virtually staged) …

With floor to ceiling windows, and balconies hanging almost over the water, these take advantage of the Saugatuck River in a way Westport seldom sees.

The Bridge at Saugatuck restaurant, Saugatuck Rowing Club and Rive Bistro all pay homage to the river. There’s a riverwalk at the medical complex. But this renovation has gone out of its way to maximize its location.

… and a bedroom (also virtually staged).

Standing in the unfurnished living rooms and bedrooms, and on the balconies — looking both upriver and downriver, with a turn of the head — I saw and considered the Saugatuck in a way I’d never done before.

The renovation is almost complete. Still to come: electric car chargers, and $75,000 worth of landscaping.

Views from the deck are both downriver …

Oleynick hopes the first tenants can move in around June 15. The Anchorage has elicited plenty of interest, from residents looking to downsize, New Yorkers looking for a weekend home, even folks looking for a rental while their own home is being renovated. All rentals are for 1 or 2 years.

… and upriver. (All photos courtesy of MLS Smart)

I’m not looking to move. I’m happy where I am. And — go figure — the price range is a little beyond what I can afford.

I must admit, though: I was intrigued. I began imagining myself in The Anchorage, on the river.

But then I looked out from one of the bedrooms, which I could convert to an office.

I know I can’t live there.

With those views of the river, I’d never get any work done.

(To learn more about The Anchorage at Saugatuck, click here.)

(“06880” regularly covers real estate — and much more, including everything Saugatuck River related. If you enjoy this hyper-local blog, please click here to support our work. Thank you!)

“Then & Now”: #15

High Point Road is the longest cul-de-sac in Westport.

It’s also the street I grew up on.

It was quite a place. Nearly every home — about 70, by the time they were all built — had 2 or 3 kids, all around my sisters’ and my ages.

We rode bikes, played in yards (and in the “circle” at the end), wandered in and out of houses. Someone’s mother fed us dinner. Then we were outside again.

Staples High School was just over the hill, on the west side of the street. We took over the athletic fields as our own.

High Point is still filled with children. It’s still a great place to grow up.

Some of the original 1950s homes remain. But many others have been torn down.

From the time Dave Matlow began photographing houses set to be demolished, and the time he stopped 6 years ago, 14 High Point homes fell to the wrecking ball. Others have been razed since.

Here is a sampling:

May 2010 …

… and May 2026.

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September 2008 …

… and May 2026.

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June 2012 …

… and May 2026.

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May 2007 …

… and May 2026. (All photos/Dave Matlow)

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And here are bonus shots. This is #34, where I grew up:

June 2017 … (Photo/Dan Woog)

… and now.

Click here for a story I wrote in 2021, when my childhood home came down.

(“06880” regularly covers Westport real estate, history … and much more. If you enjoy features like this, please click here to support our work.)

Roundup: Lacrosse Champs, Field Lights, And Non-Sports Stuff ..

Congratulations to the Staples boys lacrosse team!

The Wreckers won the FCIAC (league) championship for the 2nd time in 3 years last night. They edged New Canaan 10-9, in a nail-biter.

Seven straight 2nd-half goals gave the blue-and-whites the lead. They hung on when the Rams scored the last 5 — and their final shot hit the post.

Junior Nate Maurillo was the game’s Most Valuable Player.

Coach Will Koshansky’s squad, with a 15-4 mark — is the 5th seed in the state tournament. Play begins Wednesday (June 3, 6 p.m.), with a home match against #12 Hamden.

The last school to win both the league and state title in the same year was Darien in 2017.

Click here for a full story from The Ruden Report.

Staples High School: FCIAC champs! (Photo courtesy of Gregory Vasil for The Ruden Report)

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Speaking of sports: As the Planning & Zoning Commission plans to debate lights on 2 athletic fields (Monday, June 1, 6 p.m., Zoom), Staples High School student Loewe Epstein hopes to rally support.

He started a Change.org petition, which is nearing 200 signatures. It is focused on Wakeman Field, which is used by a variety of school teams.

Epstein cites scheduling difficulties and community involvement as key reasons to add lights.

Wakeman turf field. 

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Congratulations to Faith Sweeney!

The Coleytown Middle School gifted program teacher, and Westport Public Schools No Place for Hate coordinator, will receive the Connecticut Education Association’s Mahatma Gandhi-Martin Luther King Jr. Peace Award.

The honor recognizes an individual who has developed or implemented a program in a school or community that advances peace education, promotes cooperation, supports the peaceful resolution of conflict, and expands opportunities for students and educators.

The Westport district’s No Place for Hate initiative “helps create school communities where all students feel valued, respected, and supported. The initiative focuses on identity, bias, bullying prevention, and proactive responses that strengthen school climate across the district.”

Superintendent of schools Thomas Scarice says that Sweeney “has helped lead work that strengthens belonging, empathy and respect across our schools. This recognition speaks to her dedication to students and to the kind of school community we are always striving to build. Her work reflects the very best of Westport Public Schools and our commitment to building inclusive, caring learning communities.”

The award will be presented June 18 in Hartford.

Faith Sweeney

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A vehicle crashed into a parked car, then an apartment building yesterday afternoon at Canal Park.

The driver was treated for non-life-threatening injuries.

No one was inside the building. Fire crews shored up and stabilized the structure.

A vehicle strikes Canal Park …

… and a firefighter stabilizes the building. (Photos courtesy of Westport Fire Department)

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The Historic District Commission meets June 9 (7 p.m., Zoom).

The agenda includes discussion of demolition permits for:

  • 36 Hiawatha Lane
  • 12 Gault Park Drive
  • 1 Reimer Road
  • 15 West Parish Road.

15 West Parish Road.

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A new business is moving into Compo Shopping Center, next to Gold’s:

(Photo/Sal Liccione)

But that’s all we know. There’s no phone or email, QR code … nothing.

A quick web search brought up a “Flora Aesthetics & Wellness” in Ventura, California. An email to them bounced right back, with an error message.

Flora: We’d love to give some love to Westport’s newest aesthetics and spa place. But who are you? Contact us: 06880blog@gmail.com.

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June is Pride Month.

Westport Pride kicks it off on Monday — June 1 — with a 4 p.m. flag-raising ceremony at Jesup Green. First Selectman Kevin Christie and State Senator Ceci Maher will attend. The public is invited.

Westport Pride — the non-profit that advocates for LGBTQ+ inclusion and respect — says the Pride flag :more than a seasonal decoration. It carries history, identity, grief, celebration and visible support.

“Pride Month, observed each June, honors the legacy of LGBTQ+ activism and the ongoing pursuit of dignity and equal rights for all. This flag-raising is a public expression of Westport’s values — a visible signal to LGBTQ+ residents, families, and visitors that they are welcome and celebrated in this community.”

Westport Pride is also organizing the town-wide Pride celebration on Sunday, June 14 (12 noon, Jesup Green).

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A night of classic rock, pop and dance hits tonight (Friday, 7 p.m.) will help raise funds for Homes for the Brave, the Bridgeport-based housing, vocational skills and life coaching support non-profit serving area veterans.

The show’s site is appropriate: VFW Post 399.

The Gold Dust band will play. Admission is free, but donations are encouraged — and important.

Can’t make it, but want to help? Click here to donate!

Gold Dust

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Want to join a yacht club?

Cedar Point hosts an open house on Sunday, June 14 (4 to 6 p.m.). Everyone is invited to learn about membership, sailing and social opportunities.

The Bridge at Saugatuck will serve appetizers and cocktails.

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Four 10-minute plays — each revealing a different aspect of reproductive health care — will be staged at the Westport Country Playhouse Lucille Lortel White Barn on July 12.

“R Rated: Reproductive Rights and Resistance On Stage” — directed by Keria Naughton — is a collaboration between The A Chronicles and Reproductive Equity Now.

The performances will be followed by an open conversation exploring reproductive rights, bodily autonomy, and the realities facing today’s patients and providers. Click here for tickets, and more information.

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Jennifer Kobetitsch sends a very cute photo, for today’s “Westport … Naturally” feature.

“Baby season!” she writes. “This one was in our yard on North Avenue. Mama came back for her/him.”

(Photo/Jennifer Kobetitsch)

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And finally … on this date in 1953, Edmund Hillary and Sherpa Tenzing Norgay become the first people to reach the summit of Mount Everest.

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