Lake Country Holiday & Winter Bucket List 2021-22

Ever discover a relatively unknown band or artist that you hope deep down other people don’t also discover, so they can stay “all your own”?


That’s how we feel about Lake Country.


When we think of everything we’d want in a dream destination: winding country roads, great restaurants, incredible views and hiking, amazing community and family events, and of course, lots and lots of crystal clear waters to play and recreate on, Lake Country, the place we are so fortunate to call home, checks all the boxes. 


They can have New York City and Chicago during the holidays, we’ll take Lake Country, and everything it has to offer!


That being said, here is our “Lake Country Holiday & Winter Bucket List” for 2021-22. This is a comprehensive list of all the “must do’s”, “must see”s”, and the best holiday and seasonal food & drink during the holiday and winter months. 



1. Vintage Christmas Sale at Stone Bank Farm Market
November 17th-November 21st

Stop in during normal business hours at the Historic Stone Bank Church, and partake in some unique, vintage Christmas shopping opportunities. While doing your shopping, enjoy specialty foods from the farm, hot cider, and mulled wine. 


2. Christmas Market at The Barn
December 3rd & December 4th
Head to “The Barn” at Terra Yard Creations to find the perfect gift for that hard to buy for person. In addition to their home and gift barn being transformed into a Winter Wonderland, filled with holiday cheer and decor, they will have various local makers, artisans, and crafters showcasing their wares. To learn more, and/or to RSVP to the event CLICK HERE.



We teamed up with Lake Country Family Fun, the leading resource for all things to do with the kiddos in Lake Country, to get their top holiday and winter picks for the family. To check out their complete ‘Holiday Fun Guide’ CLICK HERE.




3. Illuminated Walk Through Country Christmas
November 19th-21st

Get the whole family in the Christmas spirit by taking a walk through the Ingleside Hotel’s Illuminated Country Christmas, and help benefit the Christmas Clearing Council of Waukesha County. Dogs are also allowed on the walking trails. CLICK HERE for exact times and for more information. **Lake Country Family Fun Top Pick

4. Downtown Oconomowoc Christmas Parade
December 4th

The Downtown Oconomowoc Christmas Parade officially lights up the holiday season. The parade is lighted as it travels through Downtown. You not only see the dazzling lights, but you’ll see a live nativity head through downtown as they prepare to present at local church, St. Matthew’s, following the parade. Be sure to have your Christmas wish lists ready for Santa, as he’ll be making an appearance, and will have his  elves in attendance collecting them. For details on exact time and location CLICK HERE.

5. Attend a Tree Lighting

The “lighting of the tree” is a Christmas tradition that’s been around for as long as we can remember. Taking the family out to an official tree lighting ceremony and celebration is a great way to get out and celebrate a holiday tradition with other friends and families in your community. Lake Country Family Fun has an amazing, and comprehensive Christmas Tree Lighting Guide.



6. Ice Castles in Lake Geneva
Opening January 2022

This bucket list item is outside of Lake Country, however, Lake Country Family Fun describes it as “a true Winter Wonderland”, making it well worth the drive as their Top Pick for winter. For more info on the opening of the Ice Castles season, and to purchase tickets CLICK HERE.



7. Winter Market at Stone Bank Farm

Every Saturday from now thru the end of the Winter season, Stone Bank Farm is playing host to local farmers, makers, and vendors from 9am-1pm. For a full list of dates and vendors CLICK HERE. 


8. Hike Nashotah Park 

With the popularity of Lapham Peak, Nashotah Park could be considered a bit of a hidden gem for hiking in Lake Country. It has tremendous trails, is extremely dog friendly, and has great trails for winter hiking. For more information on Nashotah Park check out the Waukesha County Parks page, and to view a map of the winter trails for Nashotah Park CLICK HERE.



9. Waukesha Janboree 
January, 2022

Cap off your “Bucket List” by attending the Waukesha Janboree. From fireworks, to a pancake breakfast, scavenger hunt, and so much more, the Waukesha Janboree is Wisconsin’s premier Winter Festival. Dates and further details will be announced in December. To stay up to date, CLICK HERE to check out their official website. 


10. Widow’s Wine Walk
November 19th
Calling all the “widows for the weekend” to Deer Hunters! Enjoy a night of sipping wine and strolling through, and checking out the shops of Downtown Oconomowoc. Participating shops will have wine samples, along with drink specials at the participating bars and restaurants. To learn more, and/or RSVP to the event CLICK HERE. 




11. Oconomowoc German Christmas Market
November 24th-28th
This is the 10th Anniversary of Lake Country’s biggest party and celebration of the holiday season. Awesome vendors, amazing food & drink, and all the great music, all combined with plenty of holiday cheer! What’s not to love!? For a full list of vendors, food & drink options, and schedule of entertainment, check out the German Christmas Market of Oconomowoc.


12. Healthy Holiday Inspired Treats at NONA Nutrition
Begins November 29th

We may be a partial, but we think we knocked our “Holiday & Seasonal Menu” out of the park. Featured smoothies include: Keto Holiday Spice, Keto Chocolate Mint, and Cranberry Orange. There will also be warm, healthy, low sugar hot drinks, and we’ll be dropping for the first time, a Mexican Hot Chocolate Superfood Smoothie Bowl. To view the full menu online CLICK HERE. To be the first to see announcements on the full release of the “Holiday & Seasonal Menu” be sure to follow NONA on Facebook and Instagram.


13. Winter-Beergo! 
December 4th

Head to Pewaukee Village Park for a festive holiday event hosted by MobCraft Beer and The Beergo. Hang out, enjoy some great craft beer, and Be Merry! For information, and to RSVP to the event CLICK HERE.




14. Dine in a Dome at Belfre Kitchen 

The outdoor Domes on the patio at Belfre Kitchen are back and available for booking! They can be reserved for Brunch, Lunch, and Dinner for 90 minutes, and provide an amazing outdoor dining experience during the cold winter months. And be sure to get your tickets early for their “Retro Classic Christmas Dinner” on December 15th, as tickets go fast! To check availability for the “Retro Christmas Dinner” or to reserve your own Dome, check out Belfre Kitchen.


15. Go Supper Clubbing at Palmer’s 

A family owned, and multiple award winning steakhouse in downtown Hartland is always a great choice around the holidays for get togethers over dinner with family and friends. The best steaks around, combined with that famous Midwestern Supper Club service and hospitality always makes for a great evening. Try a festive handcrafted cocktail off their seasonal drink menu like a “Bourbon Maple Winter Fashioned” or a “Winter Cosmo”. 


16. Nickel & Nickel / Dolce Dinner at Artisan 179 
January 12th
This ticketed dinner will provide for a festive, post holiday experience. Enjoy 5 courses with passed appetizers, with every course being paired with a wine from the Nickel & Nickel or Dolce Vineyards. Tickets have not yet been made available, and courses are still in the works, so be sure to check back at Artisan 179 for further details and announcements.