I cannot believe that it’s already the holiday season! Luckily, we have many local events during the holiday and winter to keep us busy. Around here, there are activities for all ages. I have a list below with six local events. Some are holiday focused, and some are not!

PS – Have you started your Christmas shopping yet? Check out my local shop local guide here right here.

German Christmas Market of Oconomowoc 

The German Christmas Market is always a popular event that usually takes place the weekend of Thanksgiving. It’s the perfect event to kick off Christmas with good food, shopping, live music, and more. Visit their website for more information.

CP Holiday Train

The CP Holiday Train is back! It’s stopping in Oconomowoc on Friday, December 9th, at 6:40 pm at the Silver Lake Street railway crossing. If you’ve never seen the Holiday Train, I highly recommend it! There’s holiday music and good cheer. You can visit their website for up-to-date information.

“A Candyland Christmas” Christmas Parade

The Oconomowoc Christmas parade is Saturday, December 3, at 5 pm! This beloved Christmas parade is presented by the Oconomowoc Kiwanis Chapter. The parade starts at Pleasant St and Walnut Street and makes its way through downtown.

Country Christmas 

This is a wonderful way to experience the magic of Christmas! The Ingleside Hotel hosts A Country Christmas with a spectacular holiday light display that you can drive through or walk through. The walk-through nights are November 18th and 19th. The drive-through nights are November 25, 2022 – November 30, 2022, and December 2, 2022 – January 1, 2023. For ticketing information, please visit their website.


This event isn’t until January, but I had to include it! The 14th Annual Chili Festival is coming up on January 28th, 2023. This event is presented by the Downtown Oconomowoc Business District. It’s the perfect mid-winter event with lots of delicious chili to try. There are other events included, such as an Ice bar, ice skating, and more! You can visit the website for more information.

BONUS: Ski Club

Little known fact, I coordinate a Ski Club at Little Switzerland every year, and this year YOU’RE INVITED! If you’re interested in skiing or snowboarding for 50% off on four Friday evenings in January, reach out or sign up here! With the free lessons included, it’s the perfect way to introduce your kids to skiing/snowboarding. I love making memories on the slopes with our children and I’m sure you will too!

Holiday Events Near Downtown Oconomowoc, WI 

The holiday season is just around the corner, and I hope it’s the best one yet for your family. Hopefully, you found a local event that you’d love to check out. My family of six has our favorite holiday traditions that we do every year. If family portraits are on your mind, now is the time to reach out and schedule them. Please send me a message here.


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