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Event Category Recreation

Upcoming Events › Recreation

November 2019

Santa’s Mailbox

November 27 - December 18

Santa’s elves will sneak into Winnetka and drop off this magical mailbox on Wednesday, November 27 on the southwest corner of Elm and Chestnut Streets in Winnetka (near the Post Office).

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December 2019

Candy Cane Lane

December 6, 2019 - January 6, 2020

Do visions of sugar plums dance in your head this holiday season? Use that creativity and register your organization, club, troop, neighborhood or family to decorate your very own tree.

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Santa’s Visit

December 7 at 10:00 am - 12:00 pm

Children will enjoy hot chocolate, pictures with Santa and his elves, a trackless train ride, cookie decorating, real reindeer, and more!

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Gingerbread House Workshop

December 11 at 5:00 pm - 6:00 pm

Using a variety of sweets and candies, children can use their creativity and imaginations to design and decorate a one-of-a-kind gingerbread house.

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Winnetka Winter Express

December 14 at 9:13 am - December 15 at 11:13 am

Choo! Choo! Come aboard the Winnetka Winter Express where children and parents will hop on a magical ride from Hubbard Woods Train Station to the North Pole. During the trip, each little boy and girl will receive a copy of a The Polar Express.

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Holiday Sing

December 24 at 6:00 pm - 6:25 pm

Join families, friends, and neighbors for the 22nd annual Holiday Sing. Bring your singing voices and your own candles (or flashlights) and gather around Village Green Park to sing everyone’s favorite holiday songs.

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January 2020

Middle School Ski Trip

January 17, 2020 at 8:00 am - 5:00 pm

Have your teenager hit the slopes at Wilmot Mountain with the Winnetka Park District for our annual Middle School Ski Trip! If your child hasn’t skied before or needs a refresher, ski instructors will be available.

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February 2020

Daddy Daughter Date Night

February 6, 2020 at 6:00 pm - 8:00 pm

New & Improved Format! Dance the night away with your favorite princess at the Rennaissance Chicago North Shore Hotel.

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March 2020

Mother Son Date Night

March 5, 2020 at 6:00 pm - 8:15 pm

New & Improved Format! Moms and sons are invited to a special evening filled with fun games, great food and dancing at Pinstripes in Northbrook!

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