Stamford's "Heights and Lights" kicked off Sunday night with Reckson's Rappelling Santa.
St. Nick and his friends went down the 22 stories of the Landmark Building before they ziplined to the library.
Local businesses also got the chance to showcase products for sale this holiday season.
"The best way to help our businesses in downtown is to have events like this and to make downtown feel welcoming, attractive, engaging and warm...we invest so much in and we take great pride in our lighting in downtown, and it creates the environment...where people want to come out to our restaurants and into our retailers as well," said Stamford Downtown President Michael Moore.
The holiday festivities ended with a colorful fireworks show spectacular.