Photos with Santa Guide Lake Country Waukesha County

Where to Find Santa in Waukesha County in 2021

Is it a tradition in your home to get a photo with Santa every year? It is for us 🙂  Santa is back out and about at places, but you can still find him waving from afar or at an outdoor only venue. Find the many different places to find Ole St. Nick around the Waukesha County and Lake Country area of Wisconsin below to snap that picture perfect moment in time.

*Our favorite Santa hangs out at the German Christmas Market

Is it a tradition for your family to have breakfast with Santa? The Breakfast with the Reindeer in Delafield is a fan favorite! Enter the giveaway here.

Check out Lake Country Family Fun’s Santa Guide to find an event near you.  More events will be added as they are announced.

Lake Country Family Fun has all your Holiday needs.

Check out our Holiday Fun Guide.

Happy Holidays from Lake Country Family Fun!

Please give a big thank you to our 2021

Photos with Santa Guide sponsor: 

Wild Elegance Photography

2021 Opportunities to See Santa

The 4th annual Feztival of Trees at The Tripoli Shrine Center 3000 W. Wisconsin Ave., Milwaukee is here!

Featuring Photos with Santa. 
Admission is $5.00 for Adults, Children 12 & Under FREE 

Santa will be checking his list twice from Saturday, November 20th through Saturday November 27th.
Bring your kids along so he knows what to leave under the tree,
kids 12 and under get in free!

More details here.

Santa will be in Watertown on select dates and times from November 27th through December 20. See the list of dates and times HERE.

Find Santa at Brookfield Square Mall in 2021!

  • In person visits will still be available, but you will have to reserve a special time to see Santa.
  • Visit Santa in the Center Court Friday, November 19 through Thursday, December 24, 2021.
  • Reserve a timeslot HERE.
  • Santa’s hours:
    • Monday – Thursday: 11am – 7pm
    • Friday – Saturday: 10am – 8pm
    • Sunday: 12pm – 6pm
    • Please note: Santa takes a break to feed the reindeer from 3pm to 4pm on Monday thru Thursday, 1pm to 2pm and 5pm to 5:45pm on Friday & Saturday, and 2:30pm to 3pm on Sunday.
  • Special Hours Information:

    • Thursday, November 25: CLOSED
    • Friday, December 24: 10am – 1pm, 2pm – 5pm
  • Santa Special Events:
    • Pet photos with Santa: November 22, November 29, December 6, December 13; from 4pm to 7pm

Now through December 24, 2021 – receive a free photo with Santa, plus free crafts and activities.

Details HERE.

Local Lake Country mom, Katie M. shares her wonderful experience HERE from 2020.

November 27 – December 24, 2020

Santa will be returning to Mayfair on Thursday, November 18, 2021. He will be visiting with guests in a socially distanced manner at level one in the Nordstrom wing.

Make this holiday magical by visiting St. Nick! Santa’s helpers have been working hard decking the halls, so don’t miss out! Take photos with Santa and create magical moments for you and your family.

Reservations are encouraged. Make them HERE.

The holiday isn’t complete without a visit with Santa! Come and greet Jolly Old St. Nick all the way from the North Pole.

See Santa at Discovery World on December 4, 11, and 18. 

RSVP to see him HERE

Visit Santa at select Sendik’s locations throughout the month of December 2021! During Santa’s scheduled appearance, enjoy holiday music from the Carribean Eclipse Duo & a holiday book signing/reading with Raejean Kanter, local children’s author of Some Call Me Santa and Two Countries, Three Friends.

Santa Schedule:

Saturday, December 4th

HARTLAND | 10:00 – 11:30 AM

GERMANTOWN | 12:30 – 2:00 PM

Sunday, December 5th

ELM GROVE | 10:00 – 11:30 AM

THE CORNERS | 12 – 1:30 PM


Sunday, December 12th

GRAFTON | 10:00 – 11:30 AM

WEST BEND | 12:30 – 2 PM

Saturday, December 18th

FRANKLIN | 10:00 – 11:30 AM

GREENFIELD | 12 – 1:30 PM

NEW BERLIN | 2:00 – 3:30 PM

The following is a list to events where Santa will be for your family to visit locally! Please note that some in person events that require advanced registration may already be full due to high demand and less opportunity. 

  • Hartland Lights

    Weekend guide Hartland Lights 2018 Lake Country Family Fun Santa


    December 2 @ 6:00 pm9:00 pm
  • Breakfast with the Reindeer, Delafield

    Breakfast with the REindeer 2021 Delafield

    Bring the whole family out for some holiday cheer and a festive atmosphere at this free event, makin…

    December 3 @ 8:00 am12:00 pm

Where to Drop Off Letters to Santa

Ebert’s Greenhouse created this template for writing letters to Santa. You can download and print at your convenience.  The template is found at the bottom of the screen through the link above. 

December 4th & 5th we’ll have activities for kids and the mailbox will be open; however, you’d be able to drop off letters anytime until until December 17th, 2021.

You can pick up a letter to Santa template at the Corners of Brookfield. 

Not local, but The Santa Claus House in Alaska, has a template available as well. 

Ebert’s Greenhouse Village in Ixonia has a special Santa mailbox in their Gift Shoppe. 

December 4th & 5th we’ll have activities for kids and the mailbox will be open; however, you’d be able to drop off letters anytime until December 17th, 2021.

The German Christmas Market event over Thanksgiving weekend, will host Santa and Mrs. Claus as well as take in letters. 

The Smiley Barn in Delafield has a Santa Mailbox. Children can write down what they want for Christmas and mail it to Santa. The store has the paper, envelopes, stamps and address.

Downtown Waukesha will have two red mailboxes to deposit your letters to Santa in. One can be found at Martha Merrill’s Books and the other at Mountaintop Coffee. There will be two additional, smaller mailboxes floating around downtown Waukesha, so visit all of the lovely small businesses and find a little red box to put your special letter to Santa in this year.

The Corners of Brookfield will have a Santa Letter Drop Off. The mailbox will be located in the Market Square Escalator vestibule.

The North Pole will be delivering a special mailbox to The Corners on Wednesday, November 24th!

New this year, all letters received by December 15th with a pre-addressed, stamped return envelope will receive a letter back from Santa!

Find all you need – including a special letter at the mailbox by Market Square starting November 24th.

This program is brought you to by LAUNCH students & The Corners who are working with Santa to bring this extra special program to the community this year!

Letters are collected at the Oconomowoc Christmas parade. The letters are collected prior to the Santa float, which is the last float. 

In Oconomowoc, if you write a letter to Santa and put your return mailing address on the letter,  the postal worker will take it and you will receive a letter back from Santa! Letters to Santa have already been rolling in to the Oconomowoc Post Office in November 2020. 

Drop Santa letters off at the Big Bend Library on December 12, 2020. 

There is a Christmas light show in Muskego called Lights on Glen Cove, that starts on Saturday, December 5, 2020. They have a cute red mailbox for Letters to Santa. Be sure to leave a return address for a Santa response!

Drop off your letters to Santa at the New Berlin Recreation Office by December 16, 2020. If you do, Santa will respond to all letters by December 25. Make sure to include your mailing address!

Throughout Waukesha County, and the USA, the postal service has added a digital letter to Santa option

The Postal Service is encouraging little ones to send in their snail mail letters through Dec. 15 to “Santa Claus 123 Elf Road, North Pole, 88888.” The Postal Service knows needs are sky-high this year, and Operation Santa workers are ready to embrace a blizzard of requests.

And for the first time ever, the letter adoption process is all digital – and nationwide. “If you live in Key West, Florida, you could log on and adopt a letter from Portland, Oregon,” Frum said.

The New Berlin community will have the opportunity for Santa Letters at their Tree Lighting event on December 4, 2021.

Hollywood Roadhouse in Nashotah has a small Santa Mailbox. 

Just outside of Lake Country, you can drop off letters to Santa at the Pfister in Milwaukee from November 26 thru December 19, 2021.

Not local, but through the The Santa Clause House in Alaska, you can order letters to Santa and whole packages from Santa. 

2021 Breakfasts with Santa

Join in for a family-friendly brunch at The Rivalry Pub at the Club at Lac La Belle. They will be utilizing both of their fabulous event spaces this year. Kids under 2 eat free!
December 5, 2021
Reservations required. 262-309-2240 and
More info HERE.

Back by popular demand, the Pfister Breakfast Buffet with Santa is a holiday tradition that creates lifelong memories.

Sundays, December 5, 12, 19, 2021 | 8:00-9:30am & 11:30am – 1:00pm

More details here.

The annual pancake breakfast with Santa at the Waukesha Masonic lodge will be December 4th starting at 8:00 am. There will be pancakes, sausage, and cold and hot drinks served. Please come and have breakfast with us during this time of healing.

Donations requested for United for Waukesha Community Fund to help our local families during a time of need. Let’s continue the healing process and begin the return to normalcy in our wonderful community. Please see flyer for details and bring your family and friends. Masks will be made available, but not required.

Cost is $5 per person.

More details HERE.

Join Rustic Manor 1848 and Saz’s Catering for our Annual Brunch with Santa! Enjoy an hour-long breakfast service where children can meet Santa as many times as they’d like in our intimate holiday experience. Manor Studios will be offering 1 complimentary photo with Santa FREE to download! Bring your cameras for other photos.

December 5, 2021

Find more details here.

Enjoy breakfast with Santa on December 5 or 12, 2021!

More details here.


Join in for the Annual Sons of the American Legion Pancakes with Santa event on December 18th, 2021 at the Flanagan Dorn American Legion Post in Hartland. This event draws hundreds of families from the Lake Country area to support the SAL mission and local Hartland Legion.

Again, this year if you bring a book – you will receive a book. This annual book exchange promotes the communities need for enhanced literacy. Extra books will be donated to local non-profits serving the Hartland community.

Santa’s elves have told SAL members he will be arriving at 9:00 a.m. – bring your camera to take your photos. SALS will not be providing photos.

Pancakes will be ready for eating at 9:00 a.m. for $5.00 a plate.

Hope to see you there!

More details here.

Oconomowoc’s Newest Bar and Grill is hosting Breakfast with Santa on December 5. Breakfast, Fun, and Memories made.

Breakfast Buffet Includes:

  • Pancakes / French Toast / Eggs / Sausage / Bacon

Santa can’t wait!!!

Snag your tickets HERE.

Come have breakfast with Santa in downtown Oconomowoc at the Cornerstone Pub and Eatery on Saturday, December 11th, 2021. 4 seatings beginning at 9:00 am, last seating at 1:30 pm. 

More details here.

December 19th from Noon to 5:00 pm 

$12 a person
2 and under are free
There will be a lunch buffet, crafts, a hot cocoa/apple cider bar, and cookie decorating. 

Santa will be there from noon to 3:00 pm 

Enjoy a Pancake Breakfast with Santa ~ Sunday, December 5 (8 a.m. to 12 p.m.)
Visit the Muskego High School cafeteria for a free pancake breakfast with Santa.
Sponsored by the Muskego Lions Club.

2021 Holiday Guides

Thanksgiving Guide Lake Country Family Fun Pumpkin Pie
the Mayhouse Collection
Holiday Craft Fair Guide Myth and Myrr
HOLIDAY CRAFT FAIR GUIDE sponsored by Brown St. Emporium
Photos with Santa Guide Lake Country Waukesha County
PHOTOS WITH SANTA GUIDE sponsored by Wild Elegance Photography
Holiday Fun Guide Corners Brookfield
HOLIDAY FUN GUIDE sponsored by
Ingleside Hotel
5 Ways to Stay Sane During Christmas Week Lake Country Family Fun
Winter Wonders
Lake Country Family Fun's Shop Small Holiday Guide
HOLIDAY SHOPPING GUIDE sponsored by local small businesses
Oconomowoc Tree Lighting Lannon Community Tree Lighting Okauchee Tree Lighting Downtown Waukesha Tree Lighting Brookfield Village Holiday Tree Lighting Pewaukee Christmas Tree Lighting Brookfield Tree Lighting Christmas Tree Lighting Annual Tree Lighting Ceremony
TREE LIGHTINGS sponsored by the Winter Farmers Market at Stone Bank Farm Market
Waukesha Christmas Parade
CHRISTMAS PARADE GUIDE sponsored by the Delafield Brewhaus
South East Wisconsin Christmas Tree Farms Guide Christmas Tree Lighting Guide
CHRISTMAS TREE FARM GUIDE sponsored by Wild Elegance Photography


If you are organizing a photo with Santa event in November or December and you would like it added to this list, please email us at erin@lakecountryfamilyfun(dot)com with your Santa photo opportunity information. You can also email us via the contact form below.
Be sure to track Santa on Christmas Eve as he makes his way to your house!
Santa Lake Country Family Fun Waukesha County


1 thought on “Where to Find Santa in Waukesha County in 2021”

  1. Santa Send Off at Tinus Marine 🙂 December 5 10-12:00!!
    Stuff the Boat Event at Tinus Marine ends on Saturday 5 with Santa visiting for socially distanced Santa pics for you and your family to participate in!! Make this year one that won’t be forgotten with “Boating with Santa” family pictures!!

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