9 Mailboxes in Milwaukee Where You Can Drop Your Letters to Santa (2022)

Santa Claus is placing his bright red mailboxes all over town 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. 1-Dec. 12, 2022

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)

1134 Vel R. Phillips Ave, Milwaukee, WI 53203
Starting November 18th, 2022

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

The Deer District will become the “Cheer District” during the holiday season, and there will be a Mailbox to the North Pole stationed near the city of Milwaukee’s Christmas tree outside the Fiserv Forum. You can find the mailbox there during the night of the tree lighting (Nov. 18, 5-7 p.m.) and into December.

Kids, be sure to include your parent’s email address to receive an email from Santa himself!

3. Colectivo Coffee

All locations

Colectivo Coffee cafe North Pole Mailbox letters to Santa Milwaukee Wisconsin

New this year, 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.

4. The Corners of Brookfield

20111 W. Bluemound Rd., Brookfield, WI 53045
Nov. 23-Dec. 22, 2022

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.

Be sure to check out the larger-than-life light installations and displays, too. You’ll find Santa’s sleigh and throne, plus a light tunnel boasting more than 16,000 lights that provide ambiance for the perfect photo opportunity or holiday stroll.

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. Santa’s Workshop

Washington Ave., Cedarburg, WI 53012
Nov. 25-Dec. 23, 2022

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. On Tuesday, December 23, Santa and Mrs. Claus will spend the evening in Cedarburg walking around and posing for photos.

8. Whitefish Bay

316 E. Silver Spring Dr., Whitefish Bay, WI 53217
Nov. 25-Dec. 23, 2022

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 on Nov. 25 at 6 p.m.

If you go on Dec. 10 (11 a.m.-1 p.m.), you can enjoy free pony rides and a meet and greet with characters from Frozen. The 3rd annual Ice Sculpture Crawl & Demonstration will take place on Dec. 17 (10 a.m.-Noon).

9. Mequon Public Market

6300 W. Mequon Rd., Mequon, WI 53092

Photo Credit: Instagram, @bauerbach2

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

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Places to Meet Santa

Unique Holiday Experiences

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