Holiday Happenings in Downtown Waukesha

Mark Your Calendars as there are some great events coming up in downtown Waukesha for the holidays. I highlighted a few of the bigger events but I see that OurDowntown.com & Waukesha Silver Bells have rather extensive calendar with great events each night of the week in Waukesha. Live music, trivia nights, poker, karaoke, open mic, dance lessons and so much more fill each night of the week in Waukesha. There is always something going on.

11/21 – TREE LIGHTING – 8 PM – 9:30 PM
I have actually never attended this but I enjoy taking pictures of the gorgeous tree every year. I might just have the opportunity to be downtown during the tree lighting and might sing a song or too with the crowd. Listen for the tone deaf girl – that’s me! 

11/23 – HOLIDAY STROLL – 12 PM -4 PM
Enjoy the wonderful shops that will be all decorated for the season and take advantage of some great sales and discounts.

11/23 – PHOTOS WITH SANTA – 12 PM – 3PM
Leticia Guzman American Family Insurance Agency on South & Grand.

11/23 – OPEN HOUSE AT THE WAUKESHA COUNTY MUSEUM – 1PM – 4PM
Enjoy a FREE afternoon at the museum before the Parade! 

11/23 – 52nd ANNUAL HOLIDAY PARADE – 4 PM – 7PM
I have made it a tradition with my friends to watch the parade every year. For the last few years we have watched the parade from the warmth of a local business on Main Street but I want to keep that a secret for fear of the place getting overcrowded. And the Packers game is at noon so no interference there. Maybe we will have to make it a day-long event with my friends again.

11/28 – BLACK FRIDAY
I’m sure the shops in downtown Waukesha will have some sort of specials for the day after Turkey Day but I haven’t heard of anything specific.

11/28 – 12/20 – HORSE DRAWN CARRIAGE RIDES – $5 per person or $12 for a family of 3 or more.
Fridays – 6 – 9 PM
Saturdays – 1 – 5 PM

11/29 – SANTA’S BREAKFAST – 8 AM – 10 AM
Martha Merrill’s Bookshop – Advanced Reservations Required – 262-547-1060

11/29 – SMALL BUSINESS SATURDAY
You better believe I will be in downtown Waukesha on Saturday supporting our local shops and buying my holiday presents. I cannot think of a better way to personalize gifts than buying local. And you truly can find something for everyone. I urge all of you to Shop Local for at least some of your gifts this year. The more money you spend locally, the more stays locally to benefit the local communities.

11/29 – FREE PHOTOS WITH SANTA – 1 PM – 3 PM
Waukesha Wireless Store – They are offering this every Saturday until Christmas

12/6 – GUINNESS BOOK OF WORLD RECORDS CELEBRATION – 4 – 5 PM
Last year, Downtown Waukesha broke the record for the most carolers in one area singing together and we are celebrating that amazing feat this year. 

12/6 – ROCKIN’ KRINGLE ART CRAWL – 4 – 10 PM
The downtown shops stay open extra late and offer great deals and discounts to get that one of a kind, unique gift for that special someone in your life. 

12/7 – SANTA RUN/WALK – 10:30 AM
I participated in this a few times and both times there was a snowfall. Last year, it was even snowing during the run and I truly had snowflakes that stayed on my nose and eyelashes. I plan to participate again this year with friends.

12/13 – UGLY CHRISTMAS SWEATER SATURDAY- ALL DAY
If you are wearing an ugly Christmas sweater, local establishments in downtown will offer you a special discount. If you have ever needed a reason to wear an ugly sweater more than just to the office party or friend’s holiday party – this is it.