Silver Bells 2020 graphic

Silver Bells – Holiday Festivities in Downtown Waukesha

The Waukesha Silver Bells festivities are a bit different in 2020, but holiday cheer is still in the air!

Join the fun in beautiful historic Downtown Waukesha area for this year’s holiday celebration, Silver Bells. Each year, Waukesha is transformed into a winter wonderland of fun and holiday magic. Take a look above at the graphic for a list of events taking place throughout the downtown area. There will be activities and entertainment for all ages from November 20th through December 26th, 2020. It will certainly be a Christmastime Celebration to remember in Downtown Waukesha this Holiday Season. You can view all the details on their webpage.

Waukesha Christmas Parade
Enjoying the Waukesha Holiday Parade in 2018.

2019 Silver Bells INFO:


Parking tip: there is 2 hour free parking at the South Street parking ramp (241 South Street). 

Plus, be sure to scroll down and enter to win a family carriage ride!

Details and photographs in this post used with permission by Silver Bells in Waukesha in conjunction with the Downtown Waukesha Business Association. 


Tree Lighting

November 22nd, 2019 at 5:30pm at the Rotunda

Holiday Stroll Downtown & Parade

Sunday, November 24th 
Parade @ 4:00 pm
“A Magical Main Street Christmas”

Santa Run

December 1st at 10:30am

Waukesha Silver Bells Art Crawl

December 7th from 4-10pm

Join us for our annual Silver Bells Art Crawl through Historic Downtown Waukesha. Select stores and shops will be open until 10 pm for and extended night of holiday shopping.

The Waukesha Art Crawl is presented by Waukesha West End Artists, UA, andJeff Seymour of SEEMOREART.CO. Our Media Sponsor is the Waukesha Freeman – Waukesha County’s Daily Newspaper. Special THANKS to Lynn & Jerry Gaffey & The Almont Gallery, Marli Connell, Bob Fesser, Connie Pelzek, ExactaGraphics, Jenn Dekorah Lee & everyone that helps out with the art crawl! For more information please visit

Letters to Santa

November 18 – December 15

Write Santa a letter and let him know what you want for Christmas! Stop by Santa’s bright red mailbox and drop off your letter address to Santa Claus by December 13. Santa’s helpers will collect the letters and make sure everyone who writes gets a personalized letter back from the big guy in the red suit.
The Letters to Santa mailbox is located at:
Martha Merrell’s Books & Toys
885 Gasper Street
Waukesha, WI 53186

Caroling for a Cause

November 15, 16, 22, 23, 29, 30 – 6:00pm -9:00pm
Dec  6, 7, 13, 14, 20, 21, 27, 28 – 6:00pm -9:00pm

Friday Music After Dark

Nov 15, 22, 29, 6, 13, 20

Get away from the holiday rush and enjoy some fun in Downtown Waukesha during the holiday season with Friday Night Music After Dark!

Pictures with Santa

November 24 at 1-3pm
Nov 30 – Dec 21st  1-3pm

A picture is worth a thousand words, and nothing is more precious than holiday pictures of your children and family with Santa Claus. The WDBA in partnership with Mountain Top Coffee, at 363 W. Main St. will be offering free photos with Mr. Claus himself from 1:00 – 3:00 p.m. every Saturday from November 30 to December 21, 2019. Santa will also be available for photos before the parade from 1 – 3 p.m. on Sunday, November 24, 2019

Carriage Rides

Friday’s 6 PM – 9 PM
Saturday’s 1 PM – 5 PM
November 29 – December 28th

Enjoy an elegant horse-drawn carriage ride through the streets of downtown Waukesha! Purchase your tickets at Martha Merrell’s Books @ 231 W Main Street. Carriage ride pickup located at Martha Merrell’s Books. Click here for a full map.

The cost for tickets is $5.00 per person or $12 for a family of three or more. Kids 2 and under ride FREE. Tickets can be purchased at Martha Merrell’s books.

Win a family carriage ride from Lake Country Family Fun!! See Below!!

12 Days of Christmas Savings

Mondays through Thursdays
December 2- 19

These special 12 days of celebration give everyone the chance to save big on holiday shopping in the Downtown Waukesha area. Shop local this Christmas season!

Cocoa & Canvas

Saturdays from 1-3 and 7-10pm
November 30 – December 14

Coming this Holiday Season Cocoa and Canvas at Stroke of Genius. Welcoming ages 8-80 $10 per person on Saturday Afternoons Santa’s Workshop from 1:00pm-3:00pm Or Saturday Evenings 7:00pm-10:00pm for adults.
Looking for a unique way to celebrate this holiday season? Want to create a beautiful, hand-painted gift or decoration you will cherish forever? Our instructors will guide you as we paint ornaments. Choose from Tiny Canvas, Wood Cutout, or Traditional Sphere. Grab a friend and create a memory! Also for the adults we’ll be serving Christmas Cocoa, w/ Schnapps, Kahlua, or Irish Creme.

Breakfast with Santa Saturdays

Nov 30, December 7, 14, 21 from 8 to 10am

Santa’s breakfast workshop will be at Martha Merrell’s Book again this year! Santa is looking forward to spending some time with all of the kids! Enjoy some hot breakfast, juice, cookies, and of course coloring and arts and crafts with Santa himself! Every Saturday (11-30 to 12-21) from 8 – 10 a.m. at 231 W. Main St.

Ugly Sweater Party

December 14th 

Join us for the annual Ugly Sweater Party! Downtown Waukesha shops & restaurants are hosting Ugly Sweater specials and parties throughout the area all day long for those who participate in the fun!


December 21st from 11-1

Come get your photo taken with live reindeer! Saturday, December 21 from 11 – 1 across from People’s Park on the corner of Clinton and Main St.

Christmas Book Readings at Martha Merrell’s

Polar Express on Dec 7 at 6pm


Small Business Saturday

November 30, 2019

Shop locally in Downtown Waukesha! The importance of locally owned small businesses was recognized by the United States Congress in 2011 and named “Small Business Saturday”. This is a day of recognition and celebration, dedicated to local shopping. The Saturday afterThanksgiving weekend is a great time for friends and family to come together and enjoy Holiday shopping. This Small Business Saturday expect to find great deals and sales at businesses of all sorts. Downtown Waukesha is a vibrant and diverse community of small businesses that offer a large variety of products and services. Join our beautiful downtown city community and support local this Small Business Saturday.

All of the information on Waukesha’s Silver Bells Festivities can be found on their website.  All details and photographs used in this posts were done so with permission from the Silver Bells in Waukesha in coordination with the Waukesha Downtown Business Association. Follow Waukesha Silver Bells on Facebook.

Giveaway Time:
Win a family carriage ride through
historic downtown Waukesha! 

Two lucky Lake Country Family Fun families will each receive a family four pack of tickets for a carriage ride through downtown Waukesha! You only need to enter once and be entered for all the opportunities. We will select the first winner on November 15th and the second on November 30th!

To Enter:

Simply enter your name and valid email address in the form below.  Be sure to also answer with your favorite seasonal event on the Facebook post from 11/4. *We will contact the winner via the email submitted in the form.

Only one entry per person. Duplicate entries will be deleted. Giveaway ends November 29th, 2019 at 11:59 pm (CST).

The giveaway has ended. 
Thank you to everyone who entered.
Congratulations to our local winners: Angela K. and Tamara K.-M.!!

Other: Entrants must be 18 years or older at the time of entering the giveaway. Entrants must be located in the U.S. The winner will be selected at random and notified via the email that was submitted. Winner must respond within 48 hours to claim their prize, or another winner will be chosen. Only one entry person. Duplicates will be deleted.

Disclosure: See disclosure and privacy policy here.  Many thanks to Silver Bells for providing the family carriage ride passes for this giveaway. The winner may be congratulated on Facebook (with the official prize notification going through email). For giveaways that are announced or promoted on Facebook, please note that these promotions are in no way sponsored, endorsed or administered by, or associated with, Facebook.

Happy Holidays and Merry Christmas!


6 thoughts on “Silver Bells – Holiday Festivities in Downtown Waukesha”

  1. I loved the christmas parade & seeing the sparkly lights & magical decorations light up downtown waukesha. Seeing all dressed in christmas attire & houses with lights also gets me into the christmas spirit.

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