If you’re visiting the Janesville area, make sure to explore Milton and Edgerton. Both of these small communities have their own unique personality, blending in to create one adventurous weekend full of stops! Whether you’re a history buff, a wine enthusiast, or simply looking to get out on the water & enjoy some nature, Milton and Edgerton have some great places worth checking out! Clocking in around 4.5 hours from the Twin City metro, these surrounding towns of Janesville are under 1-2 hours from Madison, Milwaukee, and Chicago as well! Here’s where we stopped during our weekend in Wisconsin! And don’t miss my post on all the things to do in Janesville too!
Milton
Sharla’s Coffee Stop
Kickstart your day in Milton by visiting Sharla’s Coffee Stop. Located in a beautiful historic building, this shop used to be the old Milton College Library! The coffee shop has freshly baked goodies and an impressive menu of coffee drinks (and even coffee flights coming soon!) The cozy and welcoming ambiance is perfect really for any time of day.
Milton House
Continue your journey in Milton at the Milton House, a historical gem that takes you back in time. As Wisconsin’s oldest grout-walled, cement house, built in 1844, it’s a testament to the region’s history. You can visit the grounds, lobby, and shop for free, otherwise, tours run every hour for $12/person. With the full tour, a guide takes you through the entire house, even taking you through the Underground Railroad. This is the last authenticated location in Wisconsin for the Underground Railroad.
Timber Hill Winery and Vineyard
For a little wine and lunch break, we popped into Timber Hill Winery. They have a quaint location near the Milton House but are currently about to open a beautiful new space outside of town. Â With its scenic views and exquisite wines, it’s going to be a must-stop! They have a fun weekly rotating menu of Frozen wine drinks (Frose) so I opted for one of those and Eric opted for a mixed drink and both were actually very good! Their wine menu has a lot of adventurous wines and fruit-forward wines too. We also shared an appetizer and each grabbed a sandwich that really hit the spot for the day!
North Leaf Winery
Another gem in Edgerton’s wine scene is North Leaf Winery. This family-owned establishment offers a warm and welcoming atmosphere in a really unique building! The building started as a wheat house in 1844 then went on to be a car dealership and much more. It still has its historic charm and character. I sipped a Rose that was delightful. They also have a space across the way that serves up beer on tap and other options too! Enjoy a tasting of their handcrafted wines while taking in the charming surroundings.
Sober Inn
With all the wine around, you might need a little break so make sure to check Sober Inn‘s socials for their event calendar! They are a brand new local mocktail pop-up bar that hosts events featuring friendly atmospheres, food trucks, live music, and more! The team behind Sober Inn is Melissa and Sharla (from Sharla’s Coffee Stop). These ladies and their team were so welcoming and made great NA cocktails! I love that the sober movement is hitting even rural Wisconsin for a small change of pace! My favorite had to be the Berry Blossom, a lavender lemonade with fresh mint and muddled blackberries!
Edgerton
Floating Toy
For a dose of fun, we spent most of our time in Edgerton on the water! With Floating Toy, you can rent a pontoon to head out on Lake Koshkonong! It was big enough to cruise around but small enough that we weren’t overwhelmed by an unfamiliar lake. They’ll get you all set up to take it out on your own and we packed a cooler to enjoy the day on the water with drinks and snacks. The lake also connects to the Rock River where you can float along down the river for a bit as well. I actually loved floating down the river just as much! If you’re looking for a fun way to spend the day out on the water, Floating Toy was an easy pick!
Anchor Bar and Grill
After a day out on the water, we were getting hungry for something a bit more satisfying so we popped into Anchor Bar and Grill which was right across the water from where we got on the pontoon. The place was huge and had an amazing back patio with a long list of live music all summer long! I will say our waitress honestly made our experience top-notch! She was attentive, so kind, and quick to serve us. We opted for the wings and a burger and I had the Friday Fish Fry. They definitely have your typical bar fare but it hit the spot for us. It was the perfect stop after a long day on the water.
Healing Garden
Need a moment of serenity? The Healing Garden at the Edgerton Hospital is actually one to put on your list if you enjoy flowers. I’ll be honest this isn’t usually my cup of tea, but I do love wildflowers blooming in August so I decided to make a visit as it was just a few minutes from the Anchor Bar and Grill and wow was I impressed! There are plenty of signs to direct you there to pop in and just wander through. It really was stunning and I had the whole garden to myself! It was the perfect place to take a leisurely stroll among the vibrant blooms and listen to the soothing sounds of water.
Fermenting Cellars Winery
We ended our day in Edgerton at Fermenting Cellars Winery and wow! The grounds were breathtaking as they were tucked back in a little rural oasis. They have a covered space to sit or tables amongst the hills along the fields where you can cozy up next to the fireplace or catch some sun on their grassy area. They do have food options as well and also make great frozen wine drinks too! Ps – Ask for a frozen cocktail to go! They can safely pour one for you and you can take it with you to your hotel or Airbnb to enjoy. I opted to try a wine flight where I could select my own and it was the perfect way to end the day.
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 From stepping back in time at the historic Milton House to savoring the flavors of local wineries, Edgerton and Milton were a lovely addition to our Janesville weekend, offering a blend of history, relaxation, and outdoor fun.
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