Bring in the Holidays together

The Town of Windsor is designed for good times and gatherings. Join us in the celebration of this special time of year! Your family and friends can participate in plenty of Windsor’s holiday activities.

Beginning in December, bring your holiday spirit to the Town Green for the annual Holiday Tree lighting. Or challenge your friends and neighbors for best home holiday decorating. You can even create a special memory with your little ones by dropping Christmas lists off at Santa’s Mailbox. There are festivities for everyone and always room for more holiday spirit. Learn more via our event listing below!

Light up the Town GreenDecember 1, 2022, 5-8pm on the Town Green
Deck the Halls!

Entry Deadline: December 9, 2022
Judging: Voting until December 16, 2022

The 14th Annual Charlie Brown Christmas Tree GroveDecember 1 through 31 on the Windsor Town Green
Santa's MailboxStarting: December 1, 2022

Deadline: December 15, 2022

Winter Wine WalkDecember 8, 2022 from 6-9 PM

Light up the Town Green.Underline

Thursday, December 1, 2022 | 5 - 8pm
Windsor Town Green

Join us for the 19th Annual Holiday Celebration and Tree Lighting on Thursday, December 1, 2022 from 5-8pm on the Town Green!

Deck the Halls!Underline

Entry deadline: Thursday, December 9, 2022
Voting: Week of December 15, 2022

Do you love decorating your house and yard for the holidays?

Submit your information by December 9.

Submit Your Home Here!

It’s who is around the tree.Underline

December 1 - 31, 2021 | Windsor Town Green

The 14th Annual Charlie Brown Christmas Tree Grove by People4Parks will be on display December 1 through 31 on the Windsor Town Green.

Visit the Town Green and experience the magic of over 200 individually decorated trees. For more information please go to

From Windsor to the North Pole.Underline

Starting: December 1, 2021
Deadline: December 16, 2021

Santa's Mailbox will be back on the Town Green on December 1 and ready to accept your letters!

Please include the following if you wish to receive a reply from Santa:

  • A letter with the child's name
  • A self addressed and stamped envelope
  • Letters must be received by December 16, 2021.

Windsor WinederlandUnderline

Sipping-Shopping-Dining event hosted by the Chamber of Commerce! $65 per person includes a tasting glass, food, a map of locations, and specials. A portion of proceeds benefits the Windsor Presbyterian Church Food Pantry and Clothing Closet. Participating merchants will be pouring wines and hosting holiday shopping specials to help you with your gift list needs. Stroll from store to store while relaxing with your wine tastes poured by our local wineries in each of our locations. Purchase tickets here: