8 Mailboxes in Milwaukee Where You Can Drop Your Letters to Santa (2021)

Santa 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 bring 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. 18 – Dec. 15, 2021

Santa’s elves have been busy building an official mailbox at 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!

2. The Corners of Brookfield

20111 W. Bluemound Rd., Brookfield, WI 53045
Nov. 26 – Dec. 16, 2021

Rendering by Artistic Holiday Designs

Starting November 26th, 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 the Market Square escalator vestibule. While you’re there, be sure to walk through the new Candy Corners Lane holiday lights display. It features dazzling pathways, more 4,000 feet of lights, a gingerbread house, a candy cane archway, magical selfie stations and more. More details to come soon!

Vroom Tip

Download the Vroom App to add learning to mealtime, bathtime, bedtime, or anytime with 1,000+ fun, free activities.

3. Drexel Town Square

361 W Town Square Way, Oak Creek, WI 53154
Nov. 22 – Dec. 19, 2021

Near the middle of Drexel Town Square, amid thousands of twinkling holiday lights, is the Santa’s Mailbox sponsored by B93.3 FM. Santa can’t wait to read letters from kids all over the Milwaukee area, but he’s pretty tech savvy too.  Kids — please include a parent’s email address, and you’ll receive an email reply from Santa faster!

4. Mequon Public Market

6300 W Mequon Rd, Mequon, WI 53092

Photo Credit: Instagram, @bauerbach2

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 response to their correspondence. During the holidays (Nov. 27 – Dec. 23, 2021), Natty Oaks hosts a breakfast with Santa, and they have 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. 26 – Dec. 17, 2021

The Pfister Hotel is all decked out for the holidays.

Enter the lobby of The Pfister Hotel, and you’ll find a red mailbox near the Christmas Tree where letters to Santa can be deposited for delivery to the North Pole. All letters receive a reply, and each child can get a cookie from the front desk or concierge after dropping off their letter. For kids who prefer to share their wishlists in person, The Pfister also offers a Breakfast With Santa on December 5, 12 and 19.

Vroom Tip

Download the Vroom App to add learning to mealtime, bathtime, bedtime, or anytime with 1,000+ fun, free activities.

7. Santa’s Workshop

Washington Ave., Cedarburg, WI 53012
Nov. 19 – Dec. 18, 2021

After you drop off your letter in the nearby mailbox, take a peek inside the charming 15′ x 15′ 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 Fridays and Saturdays from Nov. 19 to Dec. 18.

Note: At this time, private visits with Santa are not being scheduled due to COVID-19. Closer to the holidays, if conditions are such that Santa feels it is safe to have families inside the Workshop, he’ll be welcoming walk-up visitors and families scheduled into time slots on the day of each event.

8. Whitefish Bay

316 E. Silver Spring Dr., Whitefish Bay, WI 53217
Nov. 22 – Dec. 23, 2021

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. 26 at 6 p.m. If you go on Dec. 18, there will be an ice sculptor demonstration and crawl from 10 a.m. to noon, followed by a visit from Santa (1-3 p.m.).

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

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