PHOTOS: 12 Bright Moments in Greenwich This Holiday Season

by Jess Reid

Nothing about 2020 is typical, and so the holidays, the traditions, the time with family and friends has been and will be anything but typical.  However, in a year when folks need it most, many neighbors, businesses and organizations came up with new ideas to still keep the holiday spirit alive in Greenwich. 

After a tough year, for just about everyone, there have been many bright moments this holiday season, and here are a few worth mentioning, IMHO (in my humble opinion) and in no particular order.

GEMS lighted ambulance. Photo: Jessica Reid
GEMS lighted ambulance Santa with Maggie Reid, Sadie Tromboli and Evie Reid. Photo: Jessica Reid
  1. Greenwich Emergency Medical Service (GEMS), after many Santa inquiries during their Halloween Crawl visits to homes, obliged. They brought Santa to several families this month.  And they did this with a spectacularly decorated ambulance decked in 10,000 lights. As if this wasn’t enough, Santa traveled in the back of the ambulance providing joy and gifts to those they visited.  It’s important to note that it was the amazing GEMS staff members bringing this experience around town to families on their days off – a beyond generous gesture!   More about GEMS here:
Greenwich Ave Lights. Photo: Sebastian Dostmann
Lights on Greenwich Ave at Restoration Hardware. Photo: Jessica Reid
Greenwich holiday drive in movie. Photo: Kristen Jones
  1. If we’re talking about lights, then we must bring up the brightest display in town, the lights decorating Greenwich Ave.  Getting these lights up has been a difficult task to fund in years past, but this year, when it was more important than ever, Greenwich resident Alyssa Keleshian and the Let There Be Lights team (an initiative by the Greenwich Community Projects Fund), as well as so many generous donors, funded and organized the project.  The lights started to go up in November and will remain through January.  As if lights weren’t enough, the Greenwich Community Projects Fund provided four complimentary holiday drive-in movies these past two weekends. Thank you Alyssa, the Greenwich Community Projects Fund and to all sponsors for the brightest display of holiday spirit in town this year.  Visit for more information.
Cards and coffee for Greenwich Police. Photo: Barrie Silverman
Paying it forward with cars. Photo: Barrie Silverman
  1. A new Facebook Group, called Pay It Forward – Greenwich, where you can give or get items at no cost, took their mission to the next level for the holidays.  Group founder Stephanie Fox, with group admins and members partnered with multiple organizations this holiday season to give more.  Coordinated with the Greenwich Junior United Way, there was a holiday gift wishlist on Amazon that helped 31 families. In three short weeks, members contributed over 380 gifts for 87 children and $2,000 worth of grocery gift cards. The Pay It Forward – Greenwich group coordinated drop-offs totaling in 500 cards and $500 worth of coffee for Nathaniel Witherell nursing staff, the Greenwich Police Department, and Greenwich Hospital NICU, Labor & Delivery staff.  Well done Pay It Forward – Greenwich crew, you’ve helped hundreds of neighbors this holiday season and spread joy and cheer. If you are a Greenwich resident join the FB Group here: Photos by Barrie Silverman
Holiday Stroll.
  1. This year the annual Greenwich Holiday Stroll had to shift gears, and they did so by taking it virtual.  Understanding just how important this holiday season is to local merchants and shops they brought on over 100 businesses, organizations and sponsors from throughout town to promote them for “24 Days of Holiday Shopping & Dining.”  Merchants were given the opportunity to produce their own short videos showcasing their businesses, products and services or the TMK Event Marketing Team created custom videos for the merchants. Please take some time to check out the Greenwich Holiday Stroll website or social channels to enjoy these videos!

The 12th Annual Greenwich Reindeer Festival, featuring Santa’s three reindeer, also returned to Greenwich this year bringing some much needed holiday joy during a very challenging year! A big thank you to Sam Bridge Nursery & Greenhouses for helping to make this possible and the many other sponsors listed on the event website, The reindeer departed back to the North on December 22.

Elves and mensch say good morning to Mike Capalbo at Tod’s Point booth. Photo: Jess Reid.
  1. I may be partial to this particular season brightener as I run them all over town, but the IN Greenwich elves on a shelf and mensch on the bench definitely specialize in holiday cheer.  This is the fourth year of their visits that start at the beginning of December through Christmas Eve. They not only help promote the businesses, organizations and people they visit, but they, hopefully, offer some holiday laughter!  In 2020, Vin and Lynn, the IN Greenwich elves and Bin, short for Binyamin, the IN Greenwich mensch, who is around during Chanukah, have visited over 20 locations in town.  From sunrise at Tod’s Point with caretaker Larry Imbrogno, to enjoying pizza at the new-ish Grigg Street Pizza, some martial arts time at Greenwich Jiu Jitsu and fun with the kids at the Boys & Girls Club Greenwich, they’re spotted all over town this time of year.  Follow along on Instagram or Facebook to see where they adventure to next until they leave for the North Pole on Christmas Day.

Instagram inGreenwichCT
IN Greenwich Website:

  1. You may know Chris Jordan as the head custodian at Central Middle School, but I’ve decided he is in fact the real Santa Claus.  Chris grew out his beard this year and perfected his outfit so that he could visit many families and locations, including a visit to Kids In Crisis (KIC) coordinated by the Junior League Greenwich.  When he visited KIC in Cos Cob and inquired with the youth there what they really wanted for Christmas, one teen said he wished to reconnect with his father.  Low and behold, Chris knew a police officer in the department of the city that this teen’s father lives in. By making this connection and reaching out to the officer, a Christmas miracle is in the works. Well done Chris Jordan Krigle!  Feel free to contact Chris about Santa visits by emailing [email protected]
The volunteers at the Cos Cob Fire Police Patrol (CCFPP) brought joy to families throughout town this holiday season through “Operation Santa.”
  1. Other than by sled, there’s only one better way for Santa to travel… and that is in a fire truck.  The volunteers at the Cos Cob Fire Police Patrol (CCFPP) brought joy to families throughout town this holiday season through “Operation Santa.” Arriving in the CCFPP truck was Santa along with the Grinch, bearing gifts for everyone they visited. With sirens blazing the children of Greenwich may believe that Santa only travels in a fire truck from this point on. Great job CCFPP!  More info here:
Acacia Lodge #85 donated trees to families through Neighbor to Neighbor. Photo: Christmas Tree Committee head and Lodge Treasurer Scott Sargeant.
  1. Often we donate toys, money, food, etc. during the holidays, but imagine, assuming you celebrate Christmas, that you didn’t have a Christmas tree?  Particularly important this year, when the need is greater than ever, the Acacia Lodge #85 again teamed up with Neighbor to Neighbor to donate Christmas trees to local families who can not afford to purchase their own. This is the first Christmas tree some of these families have ever had. What brighter symbol of holiday spirit than a Christmas Tree?!  Thank you Acacia Lodge #85 for making sure this special project could happen again this year and donating 100 trees in 2020. The Acacia Lodge #85 is a 501(c)10 fraternal organization in town founded in 1857 and this year is their third year donating trees.
Greenwich Police Stuff-a-Cruiser. Photo: Jess Reid
Freccia Brothers filled a Volkswagen with 100 toy donations that went to the Greenwich Police Toy Drive. Photo: Jess Reid
  1. Donating toys has always been relatively easy this time of year, but Covid has complicated the traditional toy drive.  Luckily, the Greenwich Police Dept coordinated not one, but two days of the Stuff-A-Cruiser Toy Drive, where they filled over 10 police cruisers with toys.  Who better to safely collect toys that will go to Toys for Tots?!  Impressive job as always, Greenwich PD.  And, a shout out to Freccia Brothers Garage, who filled a Volkwagen with 100 toy donations that went to the Police Dept toy drive as well.
Cadillac Santa. Photo: Jessica Reid
  1. The myth, the legend, Cadillac Santa, has been spotted around town this past weekend.  You may have seen him driving down Greenwich Avenue or around Greenwich Point, or perhaps on the highway, like the rapper 50 Cent saw and videoed him last year.  Cadillac Santa, in his 1965 Cadillac DeVille, with the top down, drives around town bringing smiles to thousands in a season.  He throws wrapped candies to pedestrians, stops for photos, and chats with anyone just because he wants to brighten a strangers’ day.  Be on the lookout as Cadillac Santa, also known as Greenwich resident Victor Samuelsen, will return to town on December 28th as Santa, to provide holiday cheer through the New Year. Follow Cadillac Santa on his Instagram Account:
House in Riverside decorated for the holidays. Photo: Jess Reid
Illuminated tree in Greenwich Harbor courtesy of IHYC. Photo: Jess Reid
  1. It has come to my attention that fellow Greenwich residents have kicked it up a notch with their holiday decorating!  Lights and outdoor decor went up earlier this year and those that said they’d never hang lights or invest in blow up decorations changed their minds.  Thank goodness, because we need it more than ever this year.   Darlene O’Connor Raiente’s daughter took it upon herself to compile an online list, via Apple Maps, of all the local light displays and share on Facebook.  Thank you to Darlene and her daughter and to all who have gone above and beyond with their decorations to brighten your neighbors’ holiday.  Everyone feel free to keep decorations up through Christmas 2021 😉   Map Link:
Chamber of Commerce window display: Arch in Bloom.
  1. And last, but certainly not least, the Greenwich Chamber of Commerce has done a great job with promoting shopping local this holiday season.  They haven’t missed a beat with sharing business’ holiday promotions, products and services.  Brightest of all, they’ve awarded businesses for their holiday decorations and window displays.  It has been a lot of fun seeing these displays in photographs and video, shared by the Greenwich Chamber, especially when I may not have seen many of them in person otherwise.  Thank you for adding extra fun to the holiday season, Greenwich Chamber of Commerce. More info here:

I realize that the above list does not include everyone in this town that has played a role in brightening Greenwich for the 2020 holiday season, the list is already too long at 12.  Thank you to many residents, businesses, organizations, and our Board of Selectmen and departments that contributed to the above and other efforts that have become a silver lining to this year’s COVID challenges.

This list doesn’t even cover the healthcare heroes, emergency services, teachers, delivery and postal workers, staff at grocery stores and other shops that are keeping us safe or making it possible for us to receive or give gifts. 

There’s no way to ever repay them for what they do and have done during the pandemic.  In the meantime I’ll be soaking up these final holiday moments, sending happy holiday wishes to all and hoping that 2021 is as bright or brighter than this holiday season in Greenwich.

Jessica Reid lives in Riverside with her family and is a Greenwich native. She is co-owner of the digital marketing firm Greenwich Point Marketing and co-founded IN Greenwich.

Greenwich Point Marketing