“06880” Stroll: Newest Holiday Tradition A Hit!

It’s the magic of the holiday season.

The predicted rain never fell. The temperature was perfect for strolling.

Which is what hundreds of Westporters, plus out-of-town relatives and friends and strangers did last night.

Sam Betit led the Staples Orphenians in a wide range of holiday music.

“06880”‘s first-ever Holiday Stroll featured packed sidewalks, folks wandering in and out of stores for gifts (and freebies), and tons of old-fashioned neighborly fun.

Amy Saperstein (center) and friends Allegra Zemel and Stephanie Tobin strolled Main Street. (Photo/Julian Zemel, age 8)

Staples High School’s Orphenians sang. Santa posed for photos. Staples senior Sophie Alcyone painted kids’ faces.

Samta poses with Zelda and Annabel Cohen.

And Tim Stevenson and Lisa Armstrong won a $50 gift certificate to Savvy + Grace, as Ugly Sweater Contest winners.

Ugly sweater contest winners Lisa Armstrong and Tim Stevenson.

If you were there: Years from now, you can say you were at the first year of this great tradition.

If you missed it: See you in ’22!

Santa poses with the youngest stroller … (Photo/Lynn Untermeyer Miller)

… and with Staples High School 1966 graduate Pam Pollack. (Photo/Lynn Untermeyer Miller)

Face painter Sophie Alcyone at work …

… and Lila Newman shoes off the finished (cheetah) product. (Photo/Lisa Newman)

One view of the Staples Orphenians …

… and another. (Photo/Danielle Dobin)

Cider at Le Rouge Aarti Chocolatiers was one of many merchant giveaways during the “06880” Holiday Stroll.

Santa poses with artist Rosie Jon and son Leo …

… and (2nd and 3rd from left) 1st Selectwoman Jen Tooker, Planning & Zoning Commission chair Danielle Dobin, and friends.

Jeffrey Pogue was another contestant in the Ugly Sweater Contest.

And a huge shout-out to all the retailers and restaurants who participated in the “06880” Holiday Stroll:

  • Age of Reason
  • Allison Daniel Designs
  • Calico
  • Cotelac
  • Dark Horse Health & Wellness
  • Franny’s Farmacy
  • The Fred Shop
  • Joe’s Pizza
  • Kerri Rosenthal
  • Le Rouge by Aarti
  • Local to Market
  • Nic and Zoe
  • Organachs
  • Rye Ridge Delicatessen
  • Sorelle Gallery
  • The Toy Post
  • WEST
  • Westport Book Shop
  • Whip Salon
  • Winfield Street Coffee

4 responses to ““06880” Stroll: Newest Holiday Tradition A Hit!

  1. Dorothy Robertshaw

    Dan🎄❤️ you are the best thank you so much for your efforts and Fabolous contributions to our town love Dorothy and George Robertshaw

  2. Congratulations Lisa Armstrong and Tim Stevenson … well done! Tim: the red bows are stellar! 😂

  3. mary schmerker

    This is wonderful Dan. I am surprised that there are not more comments of approval and thanks for making this happen. A wonderful new Christmas tradition and a positive for downtown businesses. I suspect there will be a new Hallmark Christmas movie next year featuring Westport’s Christmas Stroll sponsored by 06880!

  4. It was lovely! Will definitely be an annual tradition for me!
    Photo credit to Julian Zemel (age 8) for ‘Amy and friends’