Friday, December 6, 2019 at 5:00 PM – 9:00 PM

Downtown New Canaan
91 Elm Street
New Canaan, CT 06840

The annual Holiday Stroll has become a family favorite for New Canaan residents and those of our neighboring towns. Downtown New Canaan transforms into something out of a Dickens’s story book. Friday night kicks off with the arrival of Santa Claus, a lighting of the trees, carol singing, live entertainment while the stores stay open late and offer refreshments and holiday cheer.

The Annual Holiday Stroll at Downtown New Canaan

As is the tradition of this highly anticipated kick-off to the holiday season in New Canaan, Friday evening will feature the arrival of Santa Claus and Mrs. Claus, who will help us officially kick off the holiday season! Residents of all ages and backgrounds gather on New Canaan’s Elm Street, which is closed to traffic, to enjoy the festivities: singing Christmas carols and enjoying musical performances by the Students of the Studio, Performing Arts Conservatory, The New Canaan Dance Academy, and the Magical Music Singers. The firepit will be glowing at the intersection of South and Elm with S’mores thanks to the Kiwanis Club of New Canaan. Don’t miss the Waffle Cabin in front of the playhouse for that once a year treat! If the weather does not cooperate, we will postpone some of Friday’s activities to Saturday so no one has to miss out!

The entertainment continues as a cast of holiday characters such as Frosty the Snowman, the Grinch and of course Rudolph roams the village spreading holiday cheer. Everyone warms up with delicious seasonal beverages provided by local merchants, as guests shop. Surprises can be found on Main and Forest Streets as well. To add to the magical atmosphere, light up holiday trinkets and garb will be available for sale during the event.

The merriment continues on Saturday: enjoy photo ops with Santa at Houlihan Lawrence at 161 Elm Street

Finally enjoy the Ginger Bread House Tour sponsored by Halstead Property which has become a New Canaan tradition for families to decorate and create together.
The houses will be on display in store windows throughout town during the month of December.