November 24 @ 4:00 pm - 7:00 pm

The 57th Annual Christmas Parade will be held on Sunday, November 24, 2019 @ 4PM. Watch as a Magical Main Street Christmas trails through the streets of Downtown Waukesha! Come down early and enjoy a Holiday Stroll through the downtown area before the parade.


November 18 - December 15

Write Santa a letter and let him know what you want for Christmas! Stop by Santa’s bright red mailbox just outside of Martha Merrell's Books & Toys at 321 W. Main St. and drop off your letter addressed to Santa Claus by December 15. 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.


November 29 - December 28

Enjoy an elegant horse-drawn carriage ride through the streets of downtown Waukesha! Purchase your tickets and hop on the carriage at Martha Merrell’s Books at 231 W. Main St. Carriage rides will run from 6 - 9 p.m. on Fridays and from 1 - 5 p.m. on Saturdays.


November 29 - December 21

Enjoy authentic Christmas caroling throughout the downtown Waukesha area during this winter holiday season and help raise money for Plowshare. Contact Sara at 262-547-5188 to sign your group up.


November 24 and November 30 - December 21

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


November 30 - December 21

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! Every Saturday (11-30 to 12-21) from 8 - 10 a.m. at 231 W. Main St.


Saturday November 30

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.


December 7 @ 4:00 pm - 10:00 pm

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


December 21 from 11 a.m. - 1 p.m.

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.


December 14

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


Monday - Thursday Dec. 2 - Dec. 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 and look for Holly Days Savings!


November 15 - December 20

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


November 30 - December 14

Come join us at Stroke of Genius for Santa's Workshop. Painting and hot cocoa for children and adults! Saturdays from 1 - 3 p.m. and 7 - 10 p.m. from November 30 to December 14.


December 7 @ 6:00 pm

Bring your family over to Martha Merrell’s for a live reading of the Polar Express.


December 1, 8, 15 from 4:00 - 6:30 pm

Sign up for a Holiday Appetizer class at Chef Pam's. Assist Chef Pam in creating three Holiday Appetizers such as Crostini with thyme roasted tomatoes, steak au poivre potato cups and creamy chicken vol-au-vent. Check out Chef Pam's Kitchen at


December 21 from 1:00 - 3:00 pm

Otto's Fine Art Academy will be hosting this Holiday Gift Making Workshop for children from 1 - 3 p.m. on Saturday, December 21, 2019. $25/child, all supplies included.


Join us in the beautiful historic downtown Waukesha area for this year's Silver Bells holiday celebration. Each year we transform our city into a winter wonderland of fun and holiday magic.  We have activities and entertainment for all ages from November 18th through December 28th. We look forward to seeing you for a Christmastime Celebration to remember.


Waukesha is the Christmas Caroling Capital of the World!

The most people caroling is 1,822 and was achieved by the Waukesha Downtown Business Association (USA) in Waukesha, Wisconsin, USA, on 22 November 2013.


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