10 Magical Santa’s Mailboxes Around Milwaukee (2023)

Santa Claus is placing his bright red mailboxes all over the Milwaukee area for your children’s letters and wish lists. Make your list, and check it twice! Then spread holiday cheer by bringing it to one of these mailboxes:

1. Cathedral Square Park

Santa’s Mailbox presented by Educators Credit Union and Serving Older Adults
520 E. Wells St., Milwaukee, WI 53202 
Nov. 7-Dec. 17, 2023

Cathedral Square Park Santa mailbox Milwaukee Wisconsin

Downtown Milwaukee has a magical connection to the North Pole right in Cathedral Square Park! Children can drop their letters into Santa’s Mailbox where wish lists will be expedited to the North Pole. 

Best of all, every boy and girl who write to Santa will receive a personalized letter in return. No postage required. Holiday spirit ensures delivery. (Be sure to include your return address so the elves know where to send the reply!)

While you’re there, be sure to check out the Milwaukee Holiday Lights Festival and Community Spirit Park, where the trees are all uniquely decorated by more than 90 local schools and organizations.

2. Cheer District (Deer District)

November 17 – December 20, 2023
Deer District Plaza near The MECCA

B93.3 FM Santa Mailbox Deer District Milwaukee Wisconsin
Photo Credit: Facebook, @B933FM

Stop by B93.3’s Santa Mailbox this holiday season, located at Cheer District, illuminated by We Energies Foundation. Bring the family down and send your holiday wishes to the North Pole! 

3. Country Christmas

2810 Golf Rd, Pewaukee, WI 53072

Find this magical mailbox in Christmas Village at the Ingleside Hotel. It shows an animated scene of the letter flying to the north pole once the child places the letter in the mailbox.  Letters to Santa are answered by elves if they choose to leave an email address.

4. The Corners of Brookfield

20111 W. Bluemound Rd., Brookfield, WI 53045

Starting November 23, kids can drop off their letters and wish lists to Santa in the North Pole mailbox at the Corners of Brookfield. The mailbox will be located in Market Square Escalator vestibule.

Be sure to check out the Corner’s holiday decorations and events, too.

NOTE: Although Santa won’t be responding to letters this year, it’s a magical opportunity for kids young and old to write to Santa!

5. Natty Oaks

11505 W. National Ave., West Allis, WI 53227
Year-round mailbox

This North Pole mailbox is out all year round in front of the Natty Oaks restaurant, and kids will get a personalized reply to their correspondence.

During the holidays (Nov. 29-Dec. 22, 2022), Natty Oaks has Santa Chalets outside that you can book Saturday-Sunday or Tuesday-Thursday. Each chalet seats up to six, and you can visit with Santa or catch him as he’s walking through 12,000 square feet of Christmas lights. Eat fresh popcorn and grab a cup of hot cocoa or cider while you wait to see the big guy.

6. The Pfister Hotel

424 E. Wisconsin Ave., Milwaukee, WI 53202
Nov. 25-Dec. 18, 2022

Enter the lobby of The Pfister Hotel, and you’ll find a red mailbox near the Christmas Tree where your child’s letter to Santa can be deposited for delivery to the North Pole.

All letters receive a personalized response, and each child can get a special gift of a cookie from the front desk or concierge after dropping off their letter.

For kids who prefer to share their Christmas lists in person, The Pfister also offers a Breakfast With Santa on December 4, 10-11 and 17-18.

7. American Family Field

1 Brewers Way, Milwaukee, WI 53214

Ensure Santa knows what’s on your wish list this year with the Brew Crew’s very own North Pole Mailbox. The mailbox will be open Tuesday, Nov. 28 through Friday, Dec. 22 inside the Left-Field entrance.

8. Milwaukee Mitchell International Airport

5601 S. 6th St., Milwaukee, WI 53221

A special “Santa’s Mailbox” is back at Milwaukee Mitchell International Airport just in time for the holiday season! Passengers flying through Concourse D can drop off their letters December 1-8.

The mailbox is near the clock tower on Concourse D. Passengers can bring their letters to the Airport or write one with the available stationery.

Alaska Airlines will fly the letters from Milwaukee to the North Pole and deliver them to Santa Claus! Responses will be mailed ahead of the holiday.

9. Santa’s Workshop

Washington Ave., Cedarburg, WI 53012
Nov. 24-Dec. 23, 2023

After you drop off your letter in the nearby mailbox, take a peek inside the charming 15×15-foot gingerbread house that graces Cedarburg’s Washington Avenue for the entire Christmas season.

Santa and Mrs. Claus will be stopping by Santa’s Workshop on select dates in November and December. Walk-up visitors will be scheduled into time slots on the same day.

10. Whitefish Bay

316 E. Silver Spring Dr., Whitefish Bay, WI 53217

The Merchants of Whitefish Bay have a direct connection to the North Pole, so they know Santa will get each letter that’s dropped off in this mailbox.

You can catch a glimpse of the man in red himself in the Holiday Stroll parade down Silver Spring Drive, taking place the Friday after Thanksgiving.

11. Mequon Public Market

6300 W. Mequon Rd., Mequon, WI 53092

12. Colectivo Coffee (TBD for 2023)

All locations

Colectivo Coffee cafe North Pole Mailbox letters to Santa Milwaukee Wisconsin

TBD for 2023: New in 2022, all Colectivo cafés will have North Pole mailboxes available for anyone – children, adults, young at heart, pet owners – to drop off a letter that needs to get to the big guy himself.

Inside each café is a darling pint-size mailbox ready to collect your letters ((along with paper and crayons to craft your correspondence). All kids will get a FREE hot chocolate (or a pup cup for dogs!) with any purchase when dropping off a letter. 

A list of Colectivo Coffee locations can be found on their website.

Do you know of another Santa’s Mailbox? Submit the information to hello@mkewithkids.com.

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About the author

In 2013, Calie Herbst, a former teacher with three little ones, saw a need for a “One Stop Shop” for family fun in Milwaukee. So she founded Milwaukee With Kids. Her goal was to find the best this city has to offer families and share it with other parents. In one place. In 2019, she published "Exploring Milwaukee WIth Kids", a comprehensive Milwaukee travel guide for families and kids. She appears regularly on WISN News, Fox 6's 'Real Milwaukee', B93.3, and Wisconsin Morning News. She has been featured in Medium, the Milwaukee Journal Sentinel, NPR, the Wisconsin Jewish Chronicle, and on CBS 58 News. Calie is available for hosting, moderating and media appearances.

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