The 2016 Holiday Stroll will be held on Friday, December 2nd and Saturday, December 3rd!


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.

Saturday includes pictures with Santa at Santa’s workshop, characters roaming the streets, more live entertainment, a Gingerbread House Tour and much more.

Delicious Food Available including Vermont's Waffle Cabin

Check out the Google 360 View of the 2015 Holiday Stroll Captured by Elizabeth Gentile of Evergreen Studios