Photos with Santa Guide Lake Country Waukesha County

Where to Find Santa in Waukesha County in 2020

Is it a tradition in your home to get a photo with Santa every year? It is for us 🙂 This year, though, things may be different. Santa will still be out and about at places, but you are more likely to 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! It’s happening in 2020 and it’s outside. 

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 2020

Photos with Santa Guide sponsor: 

Wild Elegance Photography

2020 Opportunities to See Santa

Find Santa at Brookfield Square Mall in 2020!

  • 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 27 through Thursday, December 24, 2020.
  • Reserve a timeslot HERE.
  • Santa’s hours: 
    • Monday – Saturday: 11am – 8pm
    • Sunday: 12pm – 6pm
    • Please note: Santa takes a break to feed the reindeer from 3:30pm to 4:30pm on Monday thru Saturday, and from 2pm to 2:30pm on Sunday.
  • Special Hours Information:

    • Monday, November 30: CLOSED
    • Monday, December 7: CLOSED
    • Thursday, December 24: 9am – 1pm, 2pm – 5pm

Now through December 24, 2020 – receive a free photo with Santa, plus free crafts and activities.

Details HERE.

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

November 27 – December 24, 2020

Santa will be returning to Mayfair on Friday, Nov. 27. He will be visiting with guests in a socially distanced manner at level one in the Nordstrom wing. Santa and his guests will be required to wear face coverings throughout the visit. Daily health and temperature checks will be done for all staff, Santa included, and hand sanitizing stations will be made available throughout the experience. This year more than ever, guests are strongly encouraged to make a reservation ahead of their visit through the website at

For those that are not yet comfortable visiting Santa in person, Mayfair has partnered with Jingle Ring to provide an immersive, virtual Santa experience for the entire family. Users can pre-schedule and completely personalize their contactless visit and then watch as Santa’s live magical appearance takes flight from the comfort of their homes while still partaking in one of the most cherished traditions of the season. Each visit can be joined by up to four guests, from multiple devices, bringing grandparents, aunts and uncles, cousins and other loved ones together for the experience. Reservations can be made at

Says Chris Jaeger, General Manager, Mayfair Mall, “Visits and photos with Santa are some of the most beloved and sacred traditions of the year, and as we began to plan for a holiday season unlike any other, we wanted to do all that we could to preserve the magic of this experience while still keeping our guests as safe as possible. Our hope is that by continuing to offer the opportunity to carry out these traditions, whether guests choose to participate in person or virtually, we will not only help spread the joy of the holidays, but bring a sense of normalcy to our community.”

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 

November 20 – 28, 2020.

More details here.

Santa Sightings: Keep your eye out for Santa, as he will be making his way along a special route around the Milwaukee County Zoo from 10:00 a.m. to 2:00 p.m. This year he’s been extra busy and won’t have time for photos, but he’ll be able to give you a smile and a wave.

Dates: December 12, 13, 19, & 20
*You can also drop letters to Santa on these dates. See the details below. 

The following is a list to events where Santa will either be in person or virtual accessed locally. Please note that some in person events that require advanced registration may already be full due to demand and less opportunity. 

  • Christmas Fantasy House 2021

    The Christmas Fantasy House returns this year in 2021 in a newly-constructed Pewaukee home by Victor…

    November 4 @ 10:00 am8:00 pm
    |Recurring Event (See all)

    One event on November 5, 2021 at 10:00 am

    One event on November 6, 2021 at 10:00 am

    One event on November 7, 2021 at 10:00 am

  • Christmas Fantasy House 2021

    The Christmas Fantasy House returns this year in 2021 in a newly-constructed Pewaukee home by Victor…

    November 5 @ 10:00 am8:00 pm
    |Recurring Event (See all)

    One event on November 5, 2021 at 10:00 am

    One event on November 6, 2021 at 10:00 am

    One event on November 7, 2021 at 10:00 am

  • Christmas Fantasy House 2021

    The Christmas Fantasy House returns this year in 2021 in a newly-constructed Pewaukee home by Victor…

    November 6 @ 10:00 am4:00 pm
    |Recurring Event (See all)

    One event on November 5, 2021 at 10:00 am

    One event on November 6, 2021 at 10:00 am

    One event on November 7, 2021 at 10:00 am

  • Christmas Fantasy House 2021

    The Christmas Fantasy House returns this year in 2021 in a newly-constructed Pewaukee home by Victor…

    November 7 @ 10:00 am4:00 pm
    |Recurring Event (See all)

    One event on November 5, 2021 at 10:00 am

    One event on November 6, 2021 at 10:00 am

    One event on November 7, 2021 at 10:00 am

  • 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 4 @ 8:00 am12:00 pm
  • Midnight Magic Mukwonago


    Midnight Magic Mukwonago 2020 Check out Midnight Magic in Mukwonago on Saturday, December 4, 2021. T…

    December 4 @ 10:00 am11:55 pm
  • Holiday Gift Fair with Santa

    The FBBG Holiday Gift Fair is back! Skip the Holiday shopping mall madness and enjoy a relaxed even…

    December 5 @ 10:00 am2:00 pm
  • Christmas in Dousman, Santa Comes to Town

    Save the date! We will fill Main Street in downtown Dousman with festive cheer! Walk the street and …

    December 5 @ 1:00 pm6:00 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. 

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.

The Christmas in Okauchee 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.

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 amiling 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 5, 2020.

Hollywood Roadhouse in Nashotah has a small Santa Mailbox. 

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

North Pole Mailbox at the Milwaukee County Zoo: Bring your letter for Santa and drop it off at their special North Pole mailbox (located in front of the U.S. Bank Gathering Place) and 250 letters/day will get a postcard back from Santa. Dates: December 12, 13, 19, & 20

2020 Breakfasts with Santa

Join us for a family-friendly brunch at The Rivalry Pub at the Club at Lac La Belle. We will be utilizing both of our fabulous event spaces this year to offer more seating and social-distancing options.
Reservations required. 262-309-2240 and
Seating Times:
Limiting event to 25% capacity per seating time and sanitizing between seatings.
More info HERE.

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

Saturdays, December 5 and 12, 2020.

More details here.

Enjoy breakfast with Santa on December 7!

More details here.

Enjoy brunch with Santa on December 8 and 15!

More details here and here.

Join in for the 9th Annual Sons of the American Legion Pancakes with Santa event on December 14th 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.

Come have breakfast with Santa in downtown Oconomowoc at the Cornerstone Pub and Eatery on Saturday, December 12th, 2020. Seatings at 9, 10:30, and Noon. 

More details will be coming here.

Come have lunch with Santa on December 21 at The Corners of Brookfield at Bel Air Cantina.

Come have lunch with Santa on December 21 at The Corners of Brookfield at Wahlburgers. 

More details here.

2021 Holiday Guides

Thanksgiving Guide Lake Country Family Fun Pumpkin Pie
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
Holiday Fun Guide Corners Brookfield
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
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


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 2020”

  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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