New Canaan Holiday Stroll Schedule

An easy-to-use guide to the shopping, strolling, tasting and entertainment at the Holiday Stroll. All that, and Santa, too!

                  Friday, December 2
When What Where

10 a.m.-9 p.m. 

Strolling, Shopping and Dining Downtown New Canaan 5:30-6:30 p.m. Saxe Middle School Sax Ensemble
5:30-8 p.m. Gingerbread Man 5:30– 8:30 p.m. Holiday Trinkets for Sale
5 lighted carts roaming downtown 5:30-8:30 p.m. serves homemade waffles
5:30-8:30 p.m.
Cookies served by  
Elm Street by the alley
5:30-9 p.m. Gingerbread House Tour
New Canaan Store Windows 5:30-8:30 p.m. Cathy Kangas & Neil McAuliffe
5:45 -7:30 p.m.

New Canaan Town Street Lighting and Outdoor Staged Program with MC First Selectman Rob Mallozzi:

  • 2 Little Snow Flakes Play
  • Students of the Studio, a School for the Performing Arts
  • Cast of Characters including Rudolph and Elves
  • Audience Sing-a-long with song booklets
  • Santa arrives
  • Lighting of the downtown trees
  • Performing Arts Conservatory Perfor
6-8 p.m.
Wendy Kerner Lucas, harpist

6-8:30 p.m.
Chestnut Soup prepared by Chef Brian Lewis
Elm Restaurant
6-8 p.m.
Holiday Cocktail Party

6-8 p.m.
Refreshments Available
Various New Canaan shops
6-8:30 p.m. Red Barn Applesauce and Rudi's Swiss Chocolate 6-9 p.m. Holiday reception, Waterways Exhibit Heather Gaudio Fine Art Gallery 6-8:30 p.m. Complimentary face painting & tattoos 6:30-8:30 p.m. Toy Soldier, Elf and Reindeer Sponsored by 6:30-6:40 p.m. Santa arrives on Old Faithful Sponsored by 6:45 p.m. Lighting of downtown trees
7:30-8:30 p.m. New Canaan Dance Academy
7:30-8:30 p.m. EJ the Singer Downtown New Canaan
              Saturday, December 3
When What Where 7 a.m.-noon 10 a.m.-5 p.m. Strolling, Shopping and Dining
Downtown New Canaan 10 a.m.-4 p.m. Holiday Trinkets for Sale 10:30 a.m.-3 p.m.
Elf, Reindeer and Toy Soldier
Sponsored by , WFL Real Estate and  12-4 p.m.
Come and see the clown downtown
12-12:30 p.m.

Norwalk Symphony Quintet, sponsored by the

12-1:30 p.m.
Ice Matters, Single block ice carving
12:45-1:15 p.m.
Norwalk Symphony Quintet, sponsored by the New Canaan Advertiser
New Canaan Playhouse
1-3 p.m.
Photo op with Santa in his sleigh, sponsored by New Canaan Playhouse
1:30-2 p.m. Norwalk Symphony Quintet, sponsored by the New Canaan Advertiser

1:45-3 p.m.


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