Supporting the busy holiday season for our merchants, making the shopping experience more enjoyable and festive for our residents and visitors!

Westport holiday stroll

The Westport Downtown Merchants Association will host a festive evening on Thursday, December 13 from 4:00PM to 7:00PM that invites all to come shop local and get into the holiday spirit. Stores on Main Street and all around downtown will keep their doors open until 7:00 PM, welcoming shoppers with warm hospitality and seasonal ambience that is sure to melt even the grinches heart! Enjoy strolling music around the town, complimentary Hot Cocoa served by Rye Ridge Deli, our favorite DMA elf handing out candy canes and of course, Santa will be visiting our stores throughout the evening delighting children and adults alike. Restaurants will offer featured holiday items just for our stroll night, so don’t miss out.

Valet Parking will be available in Bedford Square turning circle in front of HSBC Bank.

Please save the date and come downtown and support the wonderful shops, restaurants and people that make our town such a special place to live and visit. If this year is a success, there are plans to make this a much bigger event for 2019! The event will feature:

Holiday Music from 5:00 PM - 7:00 PM

Holiday caroling will be provided by two professional quartets, the Jolly Jingles and Frosty and the Fa La La La’s.

The Jolly Jingles and their Santa escort will start out on Riverside Avenue at Noya Fine Jewelry at 5:00 PM and make their way over the bridge, to Post Road and Jesup, stop at the mid-point on Jesup Hall and Rothbard’s patio at 6:00 PM, and head across the street to visit the Bedford Square Shops, ending at the corner of Church and Elm in front of Savannah Bee and the Library Pop-Up Shop.

Frosty and the Fa La La La’s and their jolly Santa will begin at the corner of Main Street and Avery Place and head down Main Street ending at Main Street and Post Road at 7:00 PM.



A town favorite, Horse and Wagon rides will be available on Saturday, December 15th from 12 - 4pm. The pick up location will be at the Historical Society at 25 Avery Place, directly across from Town Hall. The Historical Society will also host a family day with Santa that will include photos with Santa, holiday crafts, and a silhouette artist. This year the horse and wagon rides are brought to you by The Westport Downtown Merchants Association, The Westport Weston Chamber of Commerce and The Westport Historical Society.


At the WDMA we know that nothing adds to the holiday mood like a fun, festive atmosphere, and with that in mind we have once again challenged our merchants to outdo each other with their holiday decor by running a contest for the best downtown holiday windows. The contest will be held across three categories: national chains, independent merchants and restaurants and bars. The DMA will secure an industry professional to judge the winners, and we will also run a “People’s Choice” campaign through social media, and all participating window will be photographed and up on the WDMA website.

Winners will be chosen the week before Christmas.