Cozy Holiday Weekend

If you seek a quiet, small town holiday weekend, Whitewater, WI offers all the cozy winter wonderland magic. Whether with family or traveling as a duo, we’ve got your holiday weekend fun scheduled!

Where to stay:

With a family: Baymont Inn & Suites - Comfy. Affordable. Heated indoor pool for the kids!

As a duo: Hamilton House B&B - Romantic. Historic. In-room jacuzzi tubs!

Cozy Holiday Weekend - Day One



Jessica's Family Restaurant

Grab stick-to-your-ribs goodness from this classic diner. Provides anything from omelettes and skillets to waffles and breakfast sandwiches.


Go sledding on “Killer Hill” at Trippe Lake Park. Pop by the Sled Shed to grab what you need. Then drive to the top of the hill and fly down the 823ft slope for your morning thrill.



Second Salem Brewing Co - Warm up from your morning outside with Wisco Beer Cheese soup or Lobster Mac from this brewpub. Hot. Gooey. Oh so good.


If you don’t need a nap at this point, walk off lunch on the Trail of Many Terrains at Natureland Park. Gorgeous any time of year, there is something a little extra special about the pine forest after it has snowed.



841 Brewhouse

Winter holiday weekends need comfort food. Cozy up with family at this favorite local spot and opt for a table full of starters with "mouth-watering dippin' sauces" or fill up on a plate full of pasta. And of course, try their in-house brewed Winter Porter.


Hop in your warm car and take a tour of the neighborhoods to admire the Christmas lights. Every year, many area homes participate in Deck the House - a lighting contest that runs throughout the month of December. Pick your favorites! OR meander downtown to check out the festive Windows of Whitewater.


Candlelight Ski/Hike the Nordic Trail. Enjoy the magic of a two mile hike under the stars. Check out the DNR Events page for current details.

Treat Yourself

In the afternoon

After exploring Natureland, treat yourself to hot cocoa at The Cafe. Everyone needs a little chocolatey goodness for their afternoon pick-me-up. Feeling adventurous? Add a shot of espresso and extra whip.

In the evening

After Deck the House or a candlelight hike, treat yourself to dessert at Fanatico before you settle into your hotel or B&B for the night. Opt for the traditional tiramisu if you’re feeling the Italian dessert. Otherwise, any cake or cheesecake of the moment will certainly hit the spot.

Cozy Holiday Weekend - Day Two



Pick up a breakfast sandwich from Center St. Cafe and a coffee. In no rush? Cozy up in a booth and relax. Maybe try a Turkish coffee!


Do a little Christmas shopping at The Fuzzy Pig. This antiques and curiosities country mall just outside Whitewater has anything you might want to gift any person in your life.



Whiney's Food & Wine Bar

While you're already at The Fuzzy Pig, pop into this "fine dining in a cozy atmosphere" establishment for wood-fired pizza and a brew or grilled walleye and wine.


End your holiday weekend at the Ice Castles in Lake Geneva. This winter jaw dropper is just a short drive away from Whitewater and will leave you breathless.

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