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Weekend in Whitewater

Updated: Dec 22, 2022

I spent a weekend in Whitewater, Wisconsin, with my fabulous sister, Haley. It was a great sister weekend where we kept very busy hiking and attending local events. Whitewater would also be a perfect destination for a cozy couple getaway or trip to crush some miles on the Ice Age Trail. Here is everything you need to know for your weekend in Whitewater!


While in town, I definitely recommend staying at the stunning Hamilton House Bed & Breakfast. We had the Renoir Suite and it was incredible! We loved the fireplace, big plush robes, and attention to every detail. The building also has a mysterious history and was used for all different groups and purposes throughout the years. Gloria, the super sweet and accommodating Innkeeper, went to The Culinary Institute, so each morning guests get to start their day with the most remarkable breakfast.


Whitewater is an IAT Community and has many segments for hikers to enjoy! We met so many kind hikers over the weekend when we did the Blackhawk, Whitewater Lake, and Clover Valley segments.

Blackhawk Segment: It’s 7 miles from point to point and is the best labeled/blazed segment I’ve ever done! It provides great views of Lake La Grange and takes you along extremely tall pines and through a beautiful prairie. (We shuttled ourselves for our hikes this whole weekend– Haley parked at the finish and I met her, picked her up, and took us back to the start. After hiking, Haley drove me back to my car.) After completing Blackhawk, we went up the road to have lunch at Avant Cycle Cafe, the coolest bike shop/restaurant. They are open Friday-Sunday 10am-5pm and have breakfast options, soup, and pastries on their menu. We crushed one of their massive Boar’s Head sandwiches, and it was just what we needed after a morning of hiking!

Whitewater Lake Segment: (Near the trailhead of this segment, you can find Artesian Well with fresh spring water, so make sure you stop by to fill up your water bottle before you set out.) This stunning 4.6 mile segment was my favorite hike of the weekend! It takes you through gorgeous wooded areas and opens up to breathtaking views of Whitewater and Rice Lakes. This is one of the more challenging segments in the area, as it has a stretch with a decent amount of elevation change that makes for a great workout. I need to s/o Sprecher Brewing because thanks to them, this was the first time I got to experience Trail Magic! We walked up to a cooler of root beer for hikers to enjoy! Haley and I shared a can halfway through our hike, and we savored every refreshing sip as we were there on an oddly hot day for the season. Thank you, Sprecher! After hiking up an appetite, we headed back into town to check out 841 Brewhouse*. I highly recommend the Asiago Chicken Wraps as an appetizer. They were massive, topped with great sauce, and absolutely delicious!

Clover Valley Segment: This 1.6 mile segment is easy and super pretty, especially in the fall. It takes you along farmland and over many boardwalks. This is a State Natural Area so be sure to keep your pup on a leash and on the trail the entire hike!

As always– remember to leave no trace on the trail. Pick up after your pup and if you pack it in…pack it out!


Whitewater is such a great location for exploring the Kettle Moraine Forest area. While visiting, I highly recommend you make the short drive to check out Old World Wisconsin. Step back into the 1800s and see how Wisconsinites lived. Walk around and visit restored buildings from farms and villages of immigrants that came to different parts of Wisconsin just the way they were in the 1850s - 1910s. At most locations, you can find someone dressed like a member of the family that inhabited the house or just dressed on trend for the era. They’re ready to tell you their story and answer any questions about the family that lived in that home or the time period in general. Old World is truly a Wisconsin hidden gem!


Another gem of the area is The Fuzzy Pig. They have a beautiful farm market store, but the star of the show is Whiney’s Wine and Beer Haus. Their wine selection is incredible, the wood-fired pizza is delightful, and they have live music on the weekends! We really enjoyed the spinach and artichoke dip and the Bruschetti pizza. Next time, I’ll be sure to check out one of their wine slushies– I hear they’re great!

If you’re in need of breakfast, coffee, or a sweet treat, head to The Sweet Spot Bakehouse. They have a beautiful case of assorted baked goods, but the massive cookies and beautiful specialty cupcakes caught my eye right away. I ordered the cupcake of the month, caramel apple, and it was everything I could ask for in a dessert!

Rosa’s Pizza* downtown could be your stop for a slice or late night eat, but I also highly recommend stopping in for their build-your-own ice cream sandwich! They have two cases of Chocolate Shoppe ice cream to choose from. I chose chocolate chip cookies and stuffed them with Zanzimint– it was to die for!


As always, be sure to drink locally! Right in downtown Whitewater, you’ll find Second Salem Brewery. Due to its spooky history, Whitewater is actually known as Second Salem, and it was so fun to be there during the spooky season. The beer cans have beautiful can art, and the beers themselves are great too! I really liked the Beast of Bray Road, a nice amber. They have happy hour Monday-Friday 4-6, so be sure to stop by for a flight!


Although we kept very busy this weekend, there’s still a lot in Whitewater I need to see. I still hope to explore Taco Fresco, Fanatico (supposed to be incredible Italian), Blue Spring Lake IAT Segment, Rushing Waters Trout Farm Store, Staller Estate Winery, and many more!

*=Not dog-friendly. Restaurants without a * have a dog-friendly patio.

2 commenti

27 ott 2022

Great info!! I haven’t been to Whitewater in years!! Obviously I need to get back there—so many great places to experience!

Mi piace

Whitewater is another place I need to check out! Looks incredible 😊💕

Mi piace
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