‘New Canaan There & Then’ is sponsored by Brown Harris Stevens Realtors Bettina Hegel, Joanne Santulli, Dawn Sterner and Pam Stutz.
Long before online shopping and digital displays, New Canaan merchants had a special way of welcoming the holiday season. The Yule Window Contest brought together shopkeepers, civic organizations, and neighbors in a celebration that made downtown New Canaan the place to be each December.
The storefront decorating contest was one of New Canaan’s holiday traditions dating back to the 1940s. Local shopkeepers participated in this charming competition which was organized and sponsored by local organizations, primarily the Lions Club and the New Canaan Garden Club. This tradition beautified the town’s downtown while creating a festive atmosphere, and attracted patrons to local businesses.
Yule Window Contest judges in 1962. Photo courtesy of NCM&HS
Every year, a holiday theme was chosen to inspire the window presentations, such as: “Twas the Night Before Christmas” or “Joy to the World.” Judges ranked local shops for the most creative and detailed holiday window displays. The winner for most exquisite achievement would be awarded with a Silver Lion’s Cup, donated by the Lions Club, with runners up receiving ribbons of acknowledgement.
The windows often offered a delightful snapshot of their eras. In 1940, the Otto Cushing’s book store won with a simple elegance—two candles, a wreath, and books wrapped in colored cellophane. The 1954 winner, New Canaan Hand Crafts, impressed the judges with a scene inspired by the theme “A New England Christmas.” Praised for its detail, the storefront featured a turkey in a little oven and “children busily trimming the Christmas tree.” According to a 1954 Advertiser article, it was selected due to its balancing of tradition and modernity; “New Canaan prides itself on being a happy combination of the old and the new.”
The 1957 contest, themed “Christmas Carols,” attracted nearly 100 entries, with I. B. Woundy Company, an electrical business, taking their second Silver Lion’s Cup. The window featured electrical merchandise, holly and pine wreaths, and an organ setting of “Christmas Carols.” Woundy’s first customer was Lucius M. Monroe who hired him to install two sockets in his drug store (now known as the Cody Pharmacy housed in the New Canaan Museum) on Main Street. The cost was $1.20 – sixty-five cents for the sockets and the balance for labor.
Perhaps the most vivid display was Kathleen Inc. dress shop’s 1958 window, which celebrated “Christmas Traditions Throughout the World.” It depicted the Swedish Yuletide tradition of “Santa Lucia, Queen of Lights,” showing the loveliest girl in the village serving coffee and cakes, distinctively wearing a wreath of lighted candles on her head.
This collaborative, community-wide artistic endeavor not only brightened New Canaan’s streets but also served as a vibrant celebration of its local businesses and the unique character of the Town.
With the holidays right around the corner, the downtown is brimming with visitors enjoying the warmth and community spirit of New Canaan. Lamp posts are decorated, there are gingerbread houses in the store windows organized by the Chamber of Commerce, and the Town is in the process of raising funds for the holiday lights. Would 2026 be the year to bring back the Yule Window Contest?