The Orphenians were led by Staples High School senior Sam Betit. (Photo by Dawn Shmaruk)

WESTPORT — The first-ever 06880 Christmas Stroll held downtown on Saturday proved to be a holiday success.

Lisa Armstrong, left, of Ridgefield, and Tim Stevenson of Trumbull were the proud winners of the Ugly Sweater Contest. (Photo by Dawn Shmaruk)

The brainchild of local writer & activist Dan Woog, the 06880 blog-affiliated happening invited residents out to enjoy local shops, listen to holiday music, share an ugly sweater, and spend a few moments with the Big Man in the Red Suit.

Organizer Dan Woog watches a happy visitor share some face time with the Big Man. (Photo by Dawn Shmaruk)
The Staples Orphenians kicked off the festivities. (Photo by Dawn Shmaruk)
(Photo by Dawn Shmaruk)
The Staples High School Orphenians perform songs of the season at the 06880 Christmas Stroll. (Photo by Dawn Shmaruk)
Lila Newman, 6, of Westport sits quietly while Sophie Alcyone paints a “cheetah” design for her. (Photo by Dawn Shmaruk)
Visits with Santa and face painting were very popular events for children attending the 06880 Christmas Stroll. (Photo by Dawn Shmaruk)
The scene at the 06880 Christmas Stroll. (Photo by Dawn Shmaruk)