Supporting the busy holiday season for our merchants, the WDMA has a number of things planned to make the experience for our shoppers easier and more convenient, as well as festive!

Key activities will include:

  • Valet Parking - available on Black Friday and Weekends until December 24, and including Friday, December 23rd. Shoppers can drop off and pick up their cars at the intersection of Elm & Main Streets, between noon and 6 pm.  The cost will be $5, plus discretionary gratuity. 

This activity is sponsored by David Adam Realty


A true crowd pleaser for young and old, Santa will be visiting downtown 5 days throughout the holiday season. On the 13th and the 20th he will give his reindeer the day off and hitch a ride downtown with the Westport Fire Department on one of their shiny red trucks. 

December 13th - Meet Santa and his fire truck escort at the Paper Source and Steven Alan Patio at 4 pm.  Enjoy music by Acoustic Dizzy Fish and Paper Source will offer a “Make and Take” holiday craft for $8. 

December 20th -  Santa will arrive on the fire truck at the corner of Avery Place and Main Street at 4pm. Enjoy music by Acoustic Dizzy Fish, as well as plenty of opportunity for photos. 

Santa will also be visiting stores around downtown on the 11th from 2pm - 5pm, the 17th from 12pm - 3pm, and the 22nd at 3pm - 5pm.  



Enjoy the sounds of the season as you walk, shop and dine around downtown on various days throughout the holiday season. 

Jake Bernard - Friday November 25th and Saturday November 26th 12:30pm - 2:30pm
Orphenians Caroling - December 10th 12-2pm and December 22nd 5-7pm
Acoustic Dizzy Fish - December 13th 4-6pm and December 20th 4-6pm
Pop Music Academy - December 17th 12-3pm
Suzuki Music School - December 18th 12-3pm



Back by popular demand, Horse and Wagon rides will be available on December 22nd from 3-6pm. The pick up location will be in front of Bedford Square on Church Lane (across from Pink Sumo Sushi).



Give your little one(s) a break from all that Holiday shopping and stop by Branson Hall at Christ and Holy Trinity Church on the following days for different holiday inspired activities for kids.

Saturday November 26th 12-4pm - “Polar Express” Movie and other Holiday favorites
Saturday December 10th 12-2pm - Earthplace Crafting and Animal Encounter