Op-Ed: What Is the New Canaan Holiday Stroll All About?

For the past 16 years the weekend after Thanksgiving has been dedicated to putting the spotlight on New Canaan’s downtown stores and restaurants. 

The Holiday Stroll was started by a group of local merchants 17 years ago and has evolved to be one of New Canaan’s most beloved traditions. The Stroll allows residents and visitors to kick off the holiday shopping season by heading into downtown New Canaan to walk under the lights, look in to store windows, watch a show performed by young local talent, eat delicious food, and share your wish list with Santa.

We usually write a “Thank You” letter and publish it in the local press after the event. But we thought since we have so many new residents we should share our appreciation ahead of time, so everyone can understand how important this event is to our business district and how many people are involved in pulling it off.

We hope you will head to town this Friday evening with your friends and family. Whether you make a dinner reservation at one of or amazing restaurants or come and see the show and walk around looking for handmade gingerbread houses, the Stroll has something for everyone. Take the time to stop into stores, our local merchants plan all year and carefully curate their merchandise to feature the best gifts for everyone on your list. If you are not sure what to give head to the New Canaan Chamber of Commerce website and purchase a New Canaan gift certificate which is accepted at more than 40 local establishments.

For young families we encourage you to come back into town on Saturday between 10 a.m. and 3 p.m. to catch up with Santa who will be in front of Houlihan Lawrence at 161 Elm St.

The Chamber works for many months to produce the Stroll but could not possibly put on an event like this on without the support of the municipality and the time commitment and financial contributions of many.

• As you walk through town over the next month, please look at the lights in the trees which are 100% funded by residents and businesses who every year collectively contribute close to $25,000 to have the lights carefully and artfully strung by Hutchinson Tree Service on Elm, Main South, and Forest Streets.
• Have you noticed the lampposts? Each one was decorated with white pine garland donated by Greggs Garden Center and hung by a dedicated team of S.L.O.B.S. Check out the garland tags on each lamp post you will see the name of a business or a family who have “sponsored” that pole which helps the Chamber raise the necessary funds to put on the Holiday Stroll.
• The Gingerbread Houses you see in the window were purchased and handed out by the New Canaan office of Brown Harris Stevens; 150 families spent their Thanksgiving weekend decorating the houses which are placed in stores who volunteer precious window space for the young architects’ creations.
• Santa will be here both Friday Night and Saturday thanks to a generous contribution from the New Canaan Office of Houlihan Lawrence. On Friday night Mrs. Claus will be here thanks to our friends at Camp Playland.
• On Friday night you will see teams of National Charity League volunteers selling light up garb and trinkets. When you buy something from their cart you too will be helping fund the Holiday Stroll.
• The Show, which will take place at the Elm/South Avenue intersection will be emceed by the Town Players of New Canaan and feature performances from East School Singers, New Canaan Music, New England Academy of Dance, The Studio for Performing Arts, The Performing Arts Conservatory and Pender-Keady Academy.
• The Police, CERT, Departments of Public Works and Health, and the First Selectman’s Office all have a hand in making this event both fun and safe for everyone.

And finally, we can all do our part by shopping local. New Canaan’s business district is a terrific assortment of stores, cafes, restaurants, and service businesses. The mix of New Canaan’s business has evolved along with the seismic shifts in national retail trends. When you are downtown, you will see a unique blend of independent, regional, and nationally owned establishments. You may be surprised that over 60 businesses in town are owned and operated by women and over 20 are minority owned and operated. The result of such a diverse group of owners is a unique mix of goods and services. We cannot emphasize the importance of supporting all our businesses enough. These owners, managers and employees are our friends and neighbors who work extremely hard all year long to run their business. Keeping your shopping and dining dollars here benefits the businesses and the community at large. A vibrant downtown is one of New Canaan’s best assets.

As you can see it truly takes a village to pull off this event. New Canaan should be proud, the Holiday Stroll is truly “our” event.

The Chamber looks forward to seeing you downtown this weekend, please reach out if you have any questions.

Laura Budd 
Executive Director 
New Canaan Chamber of Commerce