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It’s the most wonderful time of the year. Right? Tis the Season for gift giving, cookie baking, and spreading cheer. One particular event is all about making the holidays special for those in need. The local organization Santa in a Shoebox has become a holiday tradition to many families across Southeastern Wisconsin. Boxes are filled with items such as toys and treats as a way to bring holiday cheer to those in need.

Santa in a Shoebox was founded by Diana Higgenbottom Anagnostopoulos. This is the 12th consecutive year that this event will take place. What started in her basement at filling 80 boxes has turned into distributing thousands of boxes over 3 counties in Wisconsin. These boxes benefit different organizations and shelters.

Coming Together

Businesses, families, and community organizations are focusing on spreading holiday cheer with others despite COVID-19 and health concerns. 2020 has been a year full of uncertainty, but what’s certain is that Santa in a Shoebox is bringing people together. In a time where human connection is continually changing, this event aims to unite.

Santa in a Shoebox benefits more than just those receiving boxes. The founder says “to be honest, I thought about maybe not doing it this year, but as far back as July, all three counties we serve expressed a willingness to do this, wanting to give back and spread kindness.”

Participating in the Event

Businesses, church groups, and community members participate to build boxes or donate items to go into boxes. You too can collect, donate, and package. Getting involved is a great way to help those in need and give back.

How to box?

Before you can wrap the box, you must fill the box. Shoeboxes that are donated should be labeled to fit specific genders and age groups.

  • Age Groups & Genders :
    • Newborns to 2 years old (Female & Male)
    • 3 to 5 years old (Female & Male)
    • 6 to 8 years old (Female & Male)
    • 9 to 12 years old (Female & Male)
    • 13 to 17 years old (Female & Male)
    • Adult (Female & Male)
    • Seniors (Female & Male)

What goes in a box?

Every kid wants to open a gift on Christmas. This event allows you the freedom of stuffing boxes with toys, treats, gifts, and toiletries, and these items all make great shoebox stuffers.

  • Stuff the shoebox with:
    • Books, Crayons, Gift Cards, Mittens, Playing Cards, Toothbrushes, Coloring books

If you do not have a physical shoe box to fill, items are greatly appreciated to donated individually. These donations can be made at the drop off locations

Kenosha Information

Kenosha kicks off Santa in a Shoebox starting on November 19, 2020. The final drop off date in December 16, 2020.

Items can be dropped off:

  • Stinebrink’s Piggly Wiggly-7600 Pershing Blvd
  • Kenosha Unified ESC Building- 3600 52nd Street
  • Comprehensive Orthopedics- 7401 104th Avenue
  • Stinebrink’s Piggly Wiggly-2801 14th Place

Racine Information

Racine kicks off the Santa in a Shoebox event at 2 locations. Starting November 19, 2020 until December 16, 2020 you can participate.

Racine drop off locations:

  • Malicki’s Piggly Wiggly-5201 Washington Avenue
  • Javier’s Cuisine- 2011 Lathrop Avenue

Follow Santa in a Shoebox on Facebook for updates here.

Milwaukee Information

The Milwaukee/Oak Creek area participates in this year’s event, starting on November 19, 2020 until December 16, 2020.

Drop off location:

  • Malicki’s Piggly Wiggly- 2201 East Rawson Avenue

For more information, contact Diana at 262-939-7375

Pet Edition

Show extra love to pets that are in need this holiday season by participating in the Santa in a Shoebox Pet Edition. Santa in a Shoebox has partnered with The Woof of Racine. This supply drive will take place starting November 18 until December 18.

Items to donate:

  • Toys & Treats
  • Canned animal food
  • Canned pumpkin
  • Cat bowls
  • Brushes
  • Waste bags

Drop off location: The Woof- 5326 Durand Avenue

Drop off time: Monday through Friday from 9 a.m. until 7 p.m.

Items can be placed in the tote outside of The Woof location.

For more information: 262-497-8787 or email


Diana Higgenbottom Anagnostopoulos says ” I see all the good in people during Christmas, I’ve been blessed to meet incredible people.”

If you want to get involved by have questions, reach out via their Facebook page here. Call for more information, by contacting Diana at 262-939-7375 or email

Rating: 5 out of 5.

Your contribution is appreciated.