Over 2,000 Westporters (and out-of-towners) of all ages (especially kids) filled downtown yesterday afternoon (and evening).
They posed for photos with Santa (and Buddy and his elves) (and in a photo booth), roasted s’mores, petted piglets, caroled with the Orphenians, sent letters to Santa, dropped off toys for the Police drive, got face paint, shopped and enjoyed store giveaways, met neighbors and friends — and did it all in perfect almost-winter weather.
The 5th annual Holiday Stroll was by far the biggest and best yet.
S’mores by Nômade, elves and more. (Photo/John Walker)
Co-sponsored by the Westport Downtown Association and “06880,” it’s our gift to the town. And the town embraced it.
Thanks to all who made it happen — especially the hard-working WDA crew (Maxx Crowley, Beth Meyer, Huong Belpedio, Brian Spurr and others). Thanks to Santa; the fabulous Staples Orphenians, characters and face painters; the retailers and restaurants and non-profits who welcomed all and handed out “stuff” — and everyone who strolled.
Staples Orphenians’ first stop, above Brandy Melville. Other caroling spots: the clock, “Tunnel of Love,” and Bedford Square courtyard. (Photo/Dan Woog)
Westport sure rocked around the Christmas tree.
And the brand-new, but looks-like-its-been-there-forever, Main Street clock.
At the clock: 1st Selectman Kevin Christie, Westport Downtown Association president Maxx Crowley, “06880” founder Dan Woog. The WDA donated the clock to the town; the WDA and “06880” co-sponsor the Holiday Stroll. (Photo/John Walker)
A classic shot. (Photo/John Walker)
Staples Players Scarlett Shope, Claire Kresser, Ellis Maroney and Seamus Brannigan are all in character. (Photo/Dan Woog)
Riverside Realty’s piglets were favorites. (Photo/Thomas Samaranayake)
Senior Cat Betit conducts the Orphenians. The day before, they sang at Radio City Music Hall. . (Photo/Dan Woog)
Orphenians singing at the clock. (Photo/John Walker)
Listening to the Orphenians. (Photo/John Walker)
(Photo/John Walker)
Annette Norton’s Savvy + Grace mailbox was filled with dozens of letters to Santa. The popular downtown store also sponsored the photo booth. (Photo/Dan Woog)
Grand Central Terminal’s enormous clock is a central meeting place.
So is the clock in New Canaan’s downtown.
Tomorrow, Westport will have its own clock. And its own easy-to-meet-up spot.
The handsome new addition — at the corner of Main and Elm Streets, where one-way Main Street becomes two-way near Gap — is a gift from the Westport Downtown Association. The flower bed at the site will be enhanced too.
Two views of the new clock.
The WDA is paying for the purchase, installation, insurance, maintenance and repairs.
The clock arrived recently. The site is being prepared today. Installation is set for tomorrow.
Just in time for the Westport Downtown Association/”06880″ Holiday Stroll on Saturday, it’s one more attraction for the 5th annual event (4 to 7 p.m.). Besides selfies with Santa and the town’s favorite piglet, visitors can take photos with the newest downtown attraction.
The clock is “a beautiful addition to Westport,” WDA president Maxx Crowley notes. Black with gold trim, and two-sided — saying “Town of Westport” and “1835,” the year of our founding — it fits in with the lampposts currently downtown, and is designed in the same style as the Grand Central clock.
Ready for installation.
“This isn’t just a clock. It is a symbol,” Crowley adds.
“It’s a symbol of our past, our progress, and our promise to future generations.
A symbol of the timeless charm that makes Westport more than a destination, it makes it home.”
Crowley — a lifelong Westporter — calls the clock “one of the greatest honors of my service” as Downtown Association president.
“It represents the elegance of old New England town centers, the character that defines our community, and the pride we feel every time we walk through our downtown.
“It will stand as a daily reminder that Westport’s story is still being written — and we are all a part of it.
The clock aligns with the WDA’s mission to beautify and enliven the town. They string the holiday lights and season greenery, and sponsor major events like the Fine Arts Festival, Westoberfest — and Saturday’s Stroll.
The clock will be installed here tomorrow.
Crowley says, “a project of this significance is never accomplished alone. Our thanks go to former selectwomen Jen Tooker, Andrea Moore and Candice Savin; and Public Works director Pete Ratkiewich and assistant town attorney Eileen Lavigne, whose leadership, support, and enthusiasm helped make this vision a reality.
“Enormous gratitude also goes to Jimmy Izzo of Izzo Electric and Marc Bolduc of Guinta Bolduc Masonry, whose craftsmanship and dedication brought the clock to life with extraordinary care.”
Crowley also thanks “the remarkable WDA board and team. Your passion for Westport is visible in every detail of this project.
“As Westport comes together this weekend, strolling, celebrating and sharing in the joy of the season, a new symbol of community pride will take its place. With every moment spent beneath it, this clock will remind us why Westport is such a special place to gather, shop, celebrate, and call home.”
Posted onDecember 1, 2025|Comments Off on Roundup: Holiday Stroll, Winter Concert, Classic Rock …
Several more favorites have joined the “06880”/Westport Downtown Association Holiday Stroll. The 5th annual event is less than a week away: this Saturday (December 6, 4 to 7 p.m.).
Joining the more than 50 merchants and vendors offering giveaways, promotions and more: Joe’s Pizza, SWTHZ, Lululemon and Massi Co. Scroll down for the full list.
The Holiday Stroll also features plenty of family fun: Orphenians caroling, photos with Santa Claus (and a piglet), face painting, and much more. (Plus the Westport Police “Toys for Tots” drive: There’s a collection box for new toys at the corner of Main and Elm Streets).
Here’s the full list of retailers and restaurants:
American Colors by Henry Lehr: 20% off Hampton Wash and American Colors clothing
Bartaco:Hot chocolate table
Bella Bridesmaids: $25 off per dress
Bloom Salon:Holiday treats, and discounted hair tinsel
Bridgewater Chocolate:Raffle for $50 gift card, with purchase
Brooks Brothers: 30% off nearly everything
Candle Caboodle: TBD
Chait Gallery/Photography Studio: 20% off all artwork, portraits in studio; $200 for 1-hour session, includes 8×10 print
Chocolatieree: Blissfully toasted & gooey S’morestick with every purchase (minimum $20)
Clarendon Fine Art: Holiday cheer; live music by Warren Bloom
Cold Fusion: Free wrapped chocolates
Core Burn Pilates:Discounted group class and private sessions (booked on day of Stroll)
Courtgirl:15-30% off storewide
Earthplace: 10% off Winter Solstice Campfire on December 21 (register here on Saturday)
Eleish Van Breems:Raffles; cider in courtyard
Everything But Water: Fit sessions; $25 off $150+ with Beach Club signup
Faherty: Refreshments and cool vibes
Fred: Gift with purchase
Gabriele’s: Buy $500 worth of gift cards; get $100 extra
It’s called “On This Silent Night.” It features Camille Saint-Saëns’ “Christmas Oratorio” and other music of the season, with harp and strings. Plus carols sung with the audience.
But this Friday’s concert (December 5, 7:30 p.m., Unitarian Universalist Congregation in Westport) also includes Chanukah songs, and works celebrating winter.
Tickets are $25 in advance, $30 at the door (students and children free). Click here to purchase.
Speaking of holiday music: Longtime Westporter Alex Anvari was on the Big Island of Hawaii yesterday.
He enjoyed the Waimea Community Chorus’ “Celebrate in Song” concert.
He especially enjoyed hearing their second number: “Hanukkah,” an original 3-part composition by Suzanne Sherman Propp.
Yes — the same Suzanne Sherman Propp who has spent over 20 years as a beloved music teacher at Greens Farms Elementary School.
And who — while growing up in Westport — sang the “Hallelujah Chorus” as the rousing finale as a choir member at Staples High School’s Candlelight Concerts, back in the 1980s.
Coincidentally, Handel’s “Hallelujah Chorus” was also performed yesterday in Waimea. It too closed out the program.
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For music of a different kind, check out Westporter Gary Shure’s classic rock band Ten$Grand.
They’re playing on December 13 at Odeen’s Restaurant in Norwalk (7 p.m.; $5 cover; reservations recommended 203-438-1741; info@odeens.com).
On January 10, they’ll be at VFW Post 399 (7 p.m.; free, with complimentary hors d’oeuvres and cake; cash bar).
(Happy December! A great month … and as the year ends, the perfect time to make a tax-deductible gift to “06880,” to support our 24/7/365 work. Just click here — and thank you!)
Comments Off on Roundup: Holiday Stroll, Winter Concert, Classic Rock …
In just 5 years, the “06880”/Westport Downtown Association Holiday Stroll has become a cherished tradition. It’s coming soon: Saturday, December 6 (4 to 7 p.m.).
The Staples Orphenians carols, Santa (selfies, and a box for letters), a DJ, face painters, Nômade’s s’mores, our own piglet, and over 50 special offerings from stores and restaurants (click here to see) draw hundreds of residents to Main Street and environs every year.
Don’t forget the Westport Police “Toys for Tots” drive. There’s a collection box for new toys at the corner of Main and Elm Streets.
But it’s really an all-Westport event. Retail and non-profit vendors will be there too, with booths filled with giveaways and fun.
They include Cobs Bread, Real & CO Candies, The Clubhouse and more.
There is something for everyone at the Holiday Stroll. See you there, a week from Saturday!
Staples Orphenians: a Holiday Stroll favorite. (Photo/Stacie Curran)
Yesterday’s gorgeous weather drew hordes of Westporters outside. They ran in Pequot Runners’ Turkey Trot. They played in Staples soccer’s annual alumni contest. They headed to Greenwich for the Wreckers’ football game.
They took walks: at Winslow Park. Around their neighborhoods. At Compo Beach.
Molly Alger took this photo (below), at Schlaet’s Point on Hillspoint Road. “Must be no one left at home cooking,” she says.
House Bill 8002 — a revised version of a controversial housing bill vetoed earlier — was signed into law Wednesday by Governor Lamont.
CT Mirror says it “expands fair rent commissions, eliminates most off-street parking requirements for smaller housing developments and requires towns to create housing growth plans, among other measures.”
Lamont said, “This bill tells mayors and first selectmen ‘What do you want your town to look like in five or 10 years? Start planning accordingly. Where do you want that housing to go? Are you going to zone accordingly? What else do you need? We want to be your partner.'”
Governor Lamont — shown here at the dedication of Westport’s 122 Wilton Road apartments in 2024 — has advocated for affordable housing legislation. (Photo/Dan Woog)
Today’s eye-catching early Thanksgiving morning “Westport … Naturally” photo comes from Rayfield Road, thanks to always-intriguing photographer Jerry Kuyper:
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