"One of my favorite Westport traditions during the Holidays is the lighting of the tree in front of Town Hall. The community gathers, the Orphenians sing, and the tree looks amazing! Please join us this year." -Jennifer Tooker, First Selectwoman of Westport
"My favorite thing is the ‘06880’/Westport Downtown Association Holiday Stroll! Main Street comes alive with families and kids; the atmosphere is small-town, friendly, and fun, at the unofficial kickoff to the season. See you there, December 7!" -Dan Woog, editor and publisher of '06880'
"Is there anything more festive or symbolic of the holidays than the lights on the Saugatuck River Bridge? I love the town’s holiday display, and we get to enjoy the view from Kawa Ni all season long.” -Bill Taibe, chef and owner of Kawa Ni, The Whelk, and Don Memo
"Westport transforms into a winter wonderland during the holiday season, creating a charming and inviting atmosphere for residents and visitors. Streets and homes are adorned with lights, festive wreaths, and decorations, turning the Town into a beautiful display of holiday spirit. It is a time filled with warmth, joy, and a sense of togetherness that I cherish deeply. The Town's unique shops offer a perfect opportunity for holiday shopping for one-of-a-kind gifts and handmade items that reflect the character of Westport. Strolling through downtown with its festive window displays and lights creates a magical backdrop for holiday shopping while supporting local businesses. Westport also celebrates the season with a variety of cultural and community events that highlight the Town's diversity. The annual tree lighting and Menorah lighting ceremonies are traditions that bring families and neighbors together in celebration. Holiday markets, concerts, and art exhibitions allow residents to enjoy different aspects of the season. These events help strengthen community bonds and foster a sense of belonging. Generosity and giving back are central to the holiday season in Westport. The community participates in charitable events like the Westport Police Department's toy drive, food donations, and other local efforts to support those in need. This spirit of kindness and compassion reflects the true essence of the season and Westport." -Foti Koskinas, Chief of Police
"Being a bit of a foodie, I love supporting our local restaurants, which often feature seasonal or holiday menus, making it a special time to enjoy festive meals with family and friends." -Bill Harmer, Executive Director of the Westport Library
"I believe what makes Westport special is how Westporters are so caring of their neighbors in need. 365 days of the year, lunch and dinner is taken to Gillespie and served to those who reside at The Gillespie Center and Hoskins Place Homeless Emergency Shelters. Other Westporters volunteer at the food pantry, the After School Program, or in one of the numerous other programs offered by Homes with Hope. The people of Westport care about their neighbors in need and that is what makes Westport a special Community. It takes a village, and Westport is a brilliant one! By the way, this generosity is not just during the Holidays but all year long! At the Holidays people pick buying gifts for our clients’ children rather than getting gifts for themselves. Isn’t that so kind?" -Helen McAlinden, President & CEO of Homes With Hope
"The Santa Run is a highlight of the holiday season. For nearly ten years, the Westport Fire Department has come to our doorstep and graced us with Santa’s presence. It’s always such a fun day for both of our kiddos.” -Craig Melvin, news anchor, and Lindsay Czarniak, sports reporter