Silver Bells – Holiday Festivities in Downtown Waukesha

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 below at the list of events taking place throughout the downtown area. There will be activities and entertainment for all ages from through December 30th. It will certainly be a Christmastime Celebration to remember in Downtown Waukesha this Holiday Season. You can view all the details on their webpage.

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. silver bells

Tree Lighting

November 16th at 5:30pm


Holiday Stroll Downtown & Parade

November 18th 12-7
Parade @ 5:30pm


Santa Run

December 2nd at 10:30am


Waukesha Silver Bells Art Crawl

December 1st from 4-10pm

Join us for our annual Silver Bells Art Crawl #104 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

October 27 – December 13

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 16, 17, 23, 24, 30 – 6:00pm -9:00pm
Dec 1, 7, 8, 14, 15, 21, 22, 28, 29 – 6:00pm -9:00pm


Friday Music After Dark

November 16, 23, 30 6:30 – 10pm
December 7, 14, 21, 28 6:30 – 10pm


Pictures with Santa

November 24 at 1-4
December 1, 8, 15, 22 1-4pm

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 Roots Coffee Bar & Cafe will be offering free photos with Mr. Claus himself. Also while you’re there don’t forget to grab some warm freshly brewed holiday coffee drinks and food at Roots Coffeebar & Cafe!



Carriage Rides

Friday’s 6 PM – 9 PM
Saturday’s 1 PM – 5 PM
November 23 – December 29th

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!!

View this post on Instagram

Thank you to all the readers that entered the Silver Bells giveaway to win a free carriage ride through downtown Waukesha! Stephanie took her little guy for an adventure there last weekend – look at all the fun they had on the carriage ride and seeing Santa at Fruits of the Spirit Candles. They are still offering carriage rides this upcoming weekend if you haven't had a chance to experience the festive downtown Waukesha area yet! #silverbells #downtownwaukesha #marthamerrellsbooks #fruitsofthespiritcandles #winterfun #festivefun #holidays #santa #carriagerides #cookiedecorating #storytime #lakecountryfamilyfun #familyfun #decemberinwisconsin #december2017 #christmas2017

A post shared by Lake Country Family Fun (@lakecountryfamilyfun) on


12 Days of Christmas Savings

November 24,
December 3, 4, 10, 11, 12, 17, 18, 19, 24

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

December 1, 8, 15

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

December 1, 8, 15, 22, 29 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!


Ugly Sweater Party

December 8th 

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!


Santa’s Breakfast Workshop

December 1, 8, 15, 22, 29

Santa’s breakfast workshop will be at Martha Merrell’s Books 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!


Christmas Book Readings at Martha Merrell’s

Polar Express on Dec 1 at 6pm
Rudolph on Dec 16 at 3pm



Family Christmas Activities

December 2, 9, 16, 23, 30 from 2-3pm

Bring your family over to Martha Merrell’s Books & Toys for some holiday Sunday group activity time! Great for the entire family and even friends.


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 this Facebook link. *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, 2018 at 11:59 pm (CST).

This giveaway has ended.
Congratulations to Lisa V. and Mindy F. for being our two lucky Lake Country Family Fun winners!

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!