There will be new faces on the Board of Education, after November’s election.
At last week’s first meeting of the 2025-26 school year, there already was one.
Anwara Olasewere joined the BOE as one of 2 Staples High School student representatives. The junior joins Souleye Kebe, a senior beginning his second year.
Though the 2 students cannot vote, they participate in discussions. Last year, Board members found their insights particularly important in areas like the proposed cellphone ban, and a new master schedule.
Anwara moved to Westport at 4 from St. Louis, for her mother’s job with MasterCard. She attended Long Lots Elementary and Bedford Middle School, before Staples.
A member of the Westport Youth Commission, Staples Student Council, Teen Awareness Group and several honor societies, she is perhaps best known as a swimmer. A sprinter (50 and 100 free) for Chelsea Piers in Stamford, she spends 15 hours a week in the pool — plus more time in the weight room. (One of her 2 sisters, Annam, who graduated in June from Staples, now swims at Stanford University.)
Anwara Olasewere
Anwara sees the Board of Ed as a natural extension of her work with Staples’ Student Council.
In her application video and subsequent interview with current members, she stressed her desire to connect the high school with the board, and to help current students.
“I’ve never been on a board before,” she notes. “I want to learn more about leadership.”
Her friends are excited to actually know a member of the Board of Education. She hopes to educate them — and many other Staples students — about it.
“They know there is a Board of Ed,” she says. “But they don’t know a lot about it.”
Board chair Lee Goldstein looks forward to working with Anwara.
“We’re in our third year of student representatives participation on our goard, and each of them has exceeded all our expectations,” she says.
“Anwara impressed us with her thoughtfulness and ability to see issues from multiple perspectives. We are excited to welcome her.”
Souleye Kebe, Westport’s other Board of Education student representative.
(“06880” regularly covers education in Westport — and the students in our schools. If you appreciate these stories, or anything else on this hyper-local blog, please click here to support us. Thank you!)
The signatures have been gathered and verified. Today, Stephen Shackelford and Jodi Harris launched their campaign for the Board of Education.
Though running as Democrats, the pair were not endorsed by the Democratic Town Committee. Those nods went to incumbent Abby Tolan and Lauren Karpf, deputy moderator of the Representative Town Meeting. Earlier this month, Karpf left the race, to seek re-election to the RTM. The DTC has decided not to replace her on the ticket.
The Republicans have nominated 4 candidates: incumbent Dorie Hordon, plus Michelle Hopson, Andy Frankel and Kaitlin Zucaro.
Board of Ed members serve staggered terms, so not every seat will be contested in November. There are currently 4 Democrats, 2 Republicans and 1 unaffiliated member on the board. Because by law one party can have only a bare majority — 4 seats — on the 7-member BOE, only 2 of the 3 Democrats could be elected. All 4 Republicans, however, could get the voters’ nod.
Shackelford is an attorney, and former RTM member. Harris recently completed a term as Staples High School PTA co-president. They say:
Today, on the first day of school, we’re excited to officially launch our campaign. Like so many families, including our own, we’re feeling that familiar mix of promise and excitement as our kids head off to another year in Westport’s public schools. It’s a powerful reminder of how fortunate we are to live in a community with exceptionally dedicated teachers, staff, coaches and administrators.
Stephen Shackelford and Jodi Harris.
Over the coming months we look forward to meeting many more of you, hearing your perspectives, and sharing our ideas. To our students, parents, teachers, staff, coaches and administrators: We wish you a wonderful, rewarding school year.
And to our neighbors: We look forward to earning your trust and your vote this November.
Shackelford and Harris’s Instagram — with information on their principles and plans — is @HarrisShackelfordBOE. Their email isharris.shackelford@gmail.com.
Posted onAugust 26, 2025|Comments Off on Roundup: Parks & Rec Programs, 1st Day Of School, Westport Community Theatre …
A technical glitch prevented yesterday’s Instagram Live conversation with Independent Party 1st selectman candidate David Rosenwaks. “06880” apologizes to those who tuned in.
For a couple of decades now on the first day of school, Pamela Long has taken a photo of elementary school children waiting at the Juniper Road/Caccamo Lane bus stop.
The faces may change, but the anticipation is always the same. Here is this year’s shot:
(Photo/Pamela Long)
Have a great year, kids.
And parents: Savor the moment. In a week or two, you’ll be dropping them off at college.
For 68 years, the Westport Community Theatre — a black box-style space in the lower level of Town Hall — has entertained local audiences.
Whether you’re a longtime audience member, or have never heard of it — read on for details for the 2025-26 season. It includes comedy and drama, and new plays and modern classics.
“Dooley at the Bar” (September 12-28): At the height of the Gilded Age, America’s favorite news analyst was Mr. Dooley — a fictitious bartender created by humorist Finley Peter Dunne. At his hole-in-the-wall tavern Mr. Dooley takes on robber barons, newspapers, political corruption, and a new century, in a hilarious one-man show.
“Conscience” (November 14-30): Connecticut premiere. In the 1950s, as Senator Joseph McCarthy rose to power through fear and intimidation, one Republican senator – Margaret Chase Smith of Maine – stood against him. This is the story of a remarkable woman who refused to back down.
“Happy Days,” by Samuel Beckett (January 30-February 15): Winnie is a middle-aged married woman determined to make the best of an absurd situation, by finding joy in little things, and hoping to catch the attention of her oblivious husband.
“The Savannah Sipping Society” (April 10-26): Four Southern women – an unemployed workaholic, a lonely widow, a boisterous good ol’ gal, and a life coach – are drawn together by fate (and an impromptu happy hour).
“The Matchmaker,” by Thornton Wilder (June 12-28). In 19th-century New York, wealthy widower and merchant Horace Vandergelder hopes to marry the milliner Irene Molloy. He turns to Dolly Levi for help, but she wants Horace for herself.
A 5-play subscription is $130 – that’s 5 plays for the price of 4 if purchased individually. Subscriptions include priority seating, and 2 bonus tickets to introduce friends to the theatre. Click here for details, or call 203-226-1983.
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La Plage — the Longshore restaurant — will close after Labor Day for the season.
They’ll reopen in early summer next year. The adjacent Inn at Longshore begins its remodeling project November 1.
The Inn and La Plage are part of the Delamar hospitality group. Dandelion — the new Westport hotel’s restaurant — holds a job fair today (Tuesday, noon to 4 p.m.0 for many positions.
A pre-opening cocktail party is set there for September 6. Organized by realtor Judy Michaelis, it’s a fundraiser for Westport Volunteer Emergency Medical Service. Click here for tickets.
The Planning & Zoning Commission meets tomorrow (Wednesday, 7 a.m. — yes, that time is correct — in Town Hall Room 201).
They are expected to immediately vote to go into an executive session to discuss pending litigation: ROAN Development Ventures vs. the P&Z, regarding the Hamlet at Saugatuck project.
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Tom Kretsch is one of Westport’s most talented, and favorite, photographers.
His exhibit “A Symphony of Color” is on display in the Westport Library’s South Gallery now through October 5.
Tomorrow (Wednesday) is the opening reception. The 6 p.m. event will be followed by a 7 p.m. conversation between him and Artists Collective of Westport co-founder Miggs Burroughs.
The Library says, “Kretsch’s background as an educator and lifelong traveler informs his ability to see beauty in the simple and the small. Whether he’s photographing New England, further afield or right here in Westport, his work speaks to his genre of peaceful places.” Click here for more details.
Congratulations to Team Schur — champions of this year’s resurrected Monday night men’s basketball league at Compo Beach.
A crowd of 50 people — including Staples head coach Dave Goldshore and associate head coach Chris Pickens — watched the title game. The scoe was 66-43.
The champions’ roster includes Jordan Schur, Travis Test, Noah Hammond, Zach But, Don Snyder, Connor Whelan, Kevin Cline, Brandon Barton and Michael Smith.
One Bad Oyster brings ska, surf and happiness to the Weston History & Culture Center’s outdoor summer concert series “Music at the Barn” on Sunday, September 7 (5:30 to 7 p.m.).
Guests should bring a lawn chair, and their own beverages. Tony Pizza Napolitano will be selling thin crust pizzas. Members of the Weston History & Culture Center receive a complimentary glass of beer or wine.
Today is the first day of school. Student energy will be high.
Yesterday marked the opening convocation for the 965 educators and support staff in the Westport Public Schools. Their energy — at a welcoming breakfast at Staples High, and the only all-staff meeting of the year — was off the charts.
There were several standing ovations, including for teachers marking milestone anniversaries in the district, and the 11 Teacher of the Year nominees. The winner, Dr. Dan Cortwright, earned special applause.
Another standing ovation: Staples Orphenians, under the direction of Lauren Pine (right), for their rendition of the national anthem.
But the biggest ovation may have been for a group that never gets one: bus drivers.
Near the beginning of his remarks, superintendent of schools Thomas Scarice singled out the work of the 60 First Student employees. He cited several incidents of “above and beyond” service — “small actions that have large impact” — and then invited the drivers to the front.
As they marched proudly down the aisles, hundreds of teachers and administrators rose to their feet, and cheered lustily.
First Student bus drivers enjoy a standing ovation.
There were cheers too for the Teacher of the Year nominees: Emily Boyle, Kim Chu, Erik Dey, Jeff Doornweerd, Jenna Giordano, Erin Hines, Eric Lawrence, Maggie Robinson, Jeremy Royster, Julie Sanzo and Katie Sullivan.
The selection of Dr. Dan Cortwright — an 8th grade science teacher at Bedford Middle School — was an affirmation of what Scarice called all the honorees: “the best of our profession.”
BMS principal Dr. Adam Rosen hailed the University of Michigan biochemistry Ph.D. as “a compassionate innovator and tireless advocate. He regularly includes the mot vulnerable students.”
Rosen said that Cortwright cultivates “creativity, belonging and engagement. He makes science come alive. His classroom is a place of challenge and joy. He inspires everyone. He teaches a master class in our district’s values.”
As head coach of the state champion and national contender Science Olympiad team, Cortwright reached out to a student in the intensive resource program. State judges said it was the first time a special needs youngster participated in the Olympiad.
After an emotional video in which that student spoke lovingly of Cortwright, he took the stage. The Teacher of the Year saluted the BMS students who made the young girl feel part of the team, then described the joy he gets from helping children “see the magic that happens when they figure things out.”
Westport Teacher of the year Dr. Dan Cortwright (right), with (from left) superintendent of schools Thomas Scarice, and assistant superintendent John Bayers.
Scarice, meanwhile, is trying to figure out artificial intelligence. So is everyone else in education.
His keynote address used the collapse of monasteries as a metaphor for colleges today.
Once central to all of European civilization, monasteries fell under the spread of a new technology: the printing press.
An array of forces — economic, demographic, political and technological — now buffet universities, Scarice said.
Combined with AI, the future is very uncertain.
Superintendent of schools Thomas Scarice. (All photos/Dan Woog)
“What does this mean for educators?” Scarice asked rhetorically.
His answer: It is an opportunity to “re-humanize” education.
For example, artificial intelligence can “lift the burdens on teachers, so they can spend more time with students. It can help us point our ethical compass to the true north. It can help us stay human-centered, and transparent.
AI is here to stay, he emphasized. The job of educators, Scarice said, is to “be architects, leading the pathway forward.”
He urged the Westport Schools “not to wait for change to happen, but to shape the way forward for students.
“If it can’t happen here in Westport,” he concluded, “it will never happen.”
AFTER THE BELL:Teacher of the Year Dr. Cortright is entering his 15th year as a WEstport teacher. Previously, he spent nearly 15 years in science research, contributing to advancements that help patients manage conditions like multiple myeloma …
The Westport Public Schools welcome 27 new teachers this year. There are also nearly 30 newly hired non-certified staff members, and 10 interns and student teachers. Combined with coaches, other extracurricular and stipend positions, and substitutes, there are nearly 1,200 WPS employees …
Scarice began the convocation with a moment of silence for Kristen Ryan Beirne. The popular and talented Bedford Middle School physical education teacher — a former star athlete at Staples — died earlier this month, after a long illness.
According to the New York Post, Manhattan developer Vessel Technologies is warning officials that they face “expensive legislation” if they reject a proposal for a 4- or 5-story, 75-unit, steel and glass apartment complex.
Among the concerns: “worsening traffic, parking shortages, safety issues, loss of privacy and environmental impacts from stormwater to wildlife.”
The Post calls Vessel “perhaps Connecticut’s most controversial develop, specializing in steel-and-glass buildings and targeting wealthy suburbs with projects that trigger the 8-30g statute.”
8-30g is a Connecticut housing regulation that overrides much local zoning and other control, if 30% of the proposed units will be rented at “affordable” rates, according to a state formula.
The original proposal for an 8-30g housing complex in Bethel.
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“06880” continues our Instagram Live conversations with the first selectman candidates today (Monday, 4 p.m.). Dave Briggs and I will chat with independent David Rosenwaks.
You can find us on Instagram @06880danwoog. We welcome your questions!
Just about every town organization was represented on Saturday at Compo Beach.
The pickleball courts were named for Tom Lowrie. The 97-year-old — “Mr. Pickleball,” to many — has done more than any to drive growth of the game here.
Among those honoring him were members of the Representative Town Meeting, Recreation Commission, Y’s Men and Sunrise Rotary Club.
A demonstration by professional players followed the ceremony.
Tom Lowrie (center), with Andrew Colabella (RTM member who helped name the courts) and Tom’s daughter Anne.
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Back at the beach yesterday: A group of friends — all Westport residents, 3 of them Staples High graduates — spent every Sunday morning since June training for a swim from Compo out to Cockenoe Island.
Yesterday morning, they did the real thing.
The water was choppy and the swim was long. But, Alex Klein says, “the experience made us all feel a tiny bit younger.”
From left: Alex Klein, Evan Rutchik, Justin Zale, Zach Bilchik, Jordan Lert, Andrew Zimmerman, Ari Pollack, Josh Shapiro, Adam Gilbert, Gary Straus. Missing: Matthew Linsky (boat support). Klein, Lert and Shapiro are Staples High School Class of 2003 graduates.
Speaking of sports: Yesterday’s Staples High School boys basketball Slam Jam was a day of action, fun — and competiton. Nearly 200 boys participated, at Bedford Middle School.
Speaking of basketball: As is often the case, competition was friendly but fierce last night, at a Compo Beach pick-up game.
Ben Meyer caught some of the action.
(Photo/Ben Meyer)
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Also last night: Eight to the Bar brought their roots music to the Levitt Pavilion.
Eight to the Bar (Photo copyright DinkinESH Fotografix)
Meanwhile, as summer fades, the riverside amphitheater continues to offer entertainment, both free and ticketed.
Tonight (Monday, August 25, 7 p.m.), is the rescheduled Josh Ritter with Bhi Bhiman show. Tickets are still available, online and at the box office. Ritter — a prolific singer-songwriter, musician and best-selling author, is known for his narrative lyrics and Americana blend of rock, country and folk.
Tomorrow (Tuesday, August 26, 7 p.m.) is a free show: the Fairfield counts, with vocalists Janet Richards and Levitt favorite Frank Mastrone.
Also ahead:
September 6 (5 p.m.): Mihali, with Soule Monde and Mr. Mota. The Twiddle co-founder returns to the Levitt for his 10th show, with his full band and special guests, plus reggae-infused Mr. Mota (with Westport roots). Click here for tickets.
September 7 (7 p.m.): Amy Irving and the Goolis Orchestra (free). She’ll offer songs by longtime friend and “Honcysuckle Rose” co-star Willie Nelson.
September 11 (7:30 p.m.): The Levitt’s annual tribute to first responders, starring DNR and in support of Westport Volunteer Emergency Medical Service. The show is free, but donations to WVEMS are encouraged.
September 14 (7 p.m.): Tedeschi Trucks Band: Levitt Pavilion fundraising gala. Click here for tickets.
September 20 (7 p.m; free): Argonaut & Wasp, with Wild & Co.: Neo-disco and folk rock.
A few more shows are in the pipeline, through October.
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VFW Post 399 hosts an array of activities: veterans’ events, blood drives, Thursday night jazz.
So why not comedy too?
4 comedians — Steve Marshall, Brad Bruckner, Cara Amore and Joe Pontillo — headline Comedy Night at the VFW on September 5 (doors open at 7 p.m., show at 8). Click here for tickets, and more information.
Also ahead: Rock star/soul singer/multi-intstrumentalist Eliot Lewis — a longtime member of the Average White Band (1989-2002) and Hall & Oates’ band (2003-23) brings his many talents to the VFW on September 27 (8 p.m.). Tickets are $15 in advance, $20 at the door; click here to purchase, and for more information.
Plus: Every Tuesday is “Burger & Brew Night” at the VFW (5-8 p.m.).
After setting 2 previous novels in Westport, 1979 Staples High School graduate Jim Noble is moving further afield.
His most recent — and 5th — book, “IOU,” is set in 1970s Norwalk.
Amazon describes it: “A struggling seaside town along the Long Island Sound is trying to rescue itself from the grips of economic depression and a malevolent force unlike anything ever seen. Caught in the carnage are seven people whose lives, loves, and hopes are altered forever.”
(Another week, another Roundup filled with news, events, photos, and random songs. If you appreciate this daily feature, please click here to support our work. Thank you!)
One Canada goose eats up to 4 pounds of grass a day.
And dumps 3 pounds of fecal matter, also daily.
Multiply that by our very large and active population of geese. That’s a lot of grass chewed up on Compo Beach, the Longshore golf course, and athletic fields.
A lot of geese poop too.
(Photo copyright/DinkinESH Fotografix)
But we don’t have to take all that lying down.
Enter … The Goosinator!
A low-tech, low-cost solution to an insistent, if not high-priority, problem, our 2 machines are already in use — with dramatic effect.
A Goosinator is a remote-controlled device that mimics a bird’s predators. Seeing it gooses geese to fly away.
Geese don’t like the Goosinator’s shape, look or color.
And — because geese are not as dumb as they look — the Goosinator imprints itself on their goose brains. Soon, just seeing the device’s vehicle sends them skedaddling.
The Goosinator came to town through Erik Barbieri. Westport’s new Parks & Recreation Department had used the tool effectively in New Britain, his previous post.
Westport was using actual, live dogs to scare the geese. The owners were “great,” Barbieri says. But the Goosinator is more effective.
And cheaper.
Seeing the Goosinator (far right), and preparing to flee.
(Connecticut allows the “termination” — aka “killing” — of a certain number of geese. But, Barbieri notes, “the optics are not good.”)
Westport’s head Goosinator is Rick Giunta. Recently retired after a long career with Parks & Rec, the Westport native now spends several early mornings a week goosinating. (That’s a goose’s favorite time to eat and poop.)
Hopefully, he’ll put himself out of a regular job. According to the Goosinator website, geese eventually get the message. Regular goosinations turn into less frequent forays.
Rick Giunta at Compo Beach, with his remote-controlled Goosinator.
An added benefit: Geese who go elsewhere lay their eggs elsewhere too.
Westport’s 2 Goosinators are used now at Compo Beach, and on athletic fields (another favorite goose territory). One may be deployed on the Longshore golf course, after the season.
Barbiieri may purchase a third Goosinator, too.
See ya! (Compo Beach photos/Carmen Roda)
“No one can argue that geese droppings aren’t an issue,” Giunta says
“But the Goosinator doesn’t harm them. It just relocates them.”
Unfortuately, Barbieri notes, Canada geese no longer fly south for the winter. They stay here — eating grass, then fouling our land.
Of course, those goosinated geese have to go somewhere. That may be another town, or private property. They prefer being near water, so they can escape predators.
“My job is to protect our parks, our facilities and their users,” Barbieri explains. “We’re trying to provide a service, in the right, humane way.”
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