When you think of a perfect getaway with your best girls, bustling cities and exotic beach resorts might come to mind. But nestled in gorgeous Wisconsin is a small gem waiting to be explored—Milton. This quaint town offers a mix of charm, history, and a sense of community, making it an ideal spot for a memorable girlfriends’ getaway to Milton, WI.

Introduction to a Delightful Retreat
Why Milton, you ask? The highways might bypass this enchanting town, but it has yet to lose an ounce of its appeal. Whether planning a solo trip or bringing along your favorite companions, Milton promises a delightful escape.
From lively wineries to traditional supper clubs and historic sites to eclectic shops—Milton’s got a lot.

If you’d like more Midwest towns to consider visiting, we’ve got you covered in this post: Midwestern Cities You Must Visit
The Lively Timber Hill Winery
The first stop on our adventure is the incredible Timber Hill Winery. Picture this—a place where laughter fills the air, and live music sets the mood as you savor a glass of exquisite wine.
Timber Hill offers indoor and outdoor seating, making it perfect for any weather. There’s always something happening here, from book clubs to trivia nights and even corn hole games.
For a pocket-friendly price, you can sample five different wines at Timber Hill Winery. My personal favorite? The Big Buck Blueberry.
And don’t miss out on their delicious snacks. Sara and I couldn’t resist the onion dip and house-made chips. The vibrant atmosphere and youthful crowd make Timber Hill a destination not to be missed.

The Laid-back North Leaf Winery
If you prefer a more relaxed vibe, head over to Northleaf Winery. This place is perfect for unwinding with friends. Not only do they offer wine, but also delightful pairings like wine & chocolate or wine & cheese.
The ambiance is inviting, adorned with trinkets and unique stocking stuffers.
Their award-winning wines are a testament to their excellence. I tried the Blueberry Rare Blend, which was outstanding. The wine and chocolate pairing was another highlight, with six different confections complementing each sip.
We could have easily spent hours here, chatting and savoring the flavors. Fun fact—Northleaf can ship to many states!

Shopping on Your Girlfriends’ Getaway to Milton
Milton is home to a few darling shops you won’t miss. One standout is Hattie & Elsie, a gorgeous store filled with curated goods: decorative housewares, gifts, and fun accessories.
I bought a charming camper tea light holder that is perfect for outdoor picnics. And as girlfriends would, we couldn’t resist trying on the cute weathered caps for an Instagram-worthy photo.

Another gem is the Red Rooster inside the Old Junction Mill. This 150-year-old renovated feed mill has treasures from nearly 50 artisan contributors. I loved the pet gifts and jewelry selections but went home with a Wisconsin t-shirt. It’s a shopping experience that’s sure to delight.

The Ice Age Trail
Ready for some adventure? Lace up your hiking boots and hit the Ice Age Trail! This picturesque path offers fresh air and beautiful scenery. Plus, it’s steeped in history—Abraham Lincoln once camped in these very woods! Hikers can find the trailhead on E. Storrs Lake Road.
So gather your friends and immerse yourself in nature; it’s a perfect way to balance your shopping and wine tasting with outdoor exploration.

Milton House Museum
Step back in time at the Milton House Museum, a top spot and National Historic Landmark, to explore the Underground Railroad’s history in Wisconsin. This historic museum once served as a haven for those seeking refuge, with rock tunnels leading to freedom.

The Milton House Museum offers a glimpse into this compelling history with period furnishings and artifacts. It’s a moving experience that reminds us of the importance of this chapter in American history.
Please note they are closed on Mondays; tours are $15 per adult.

Breakfast or Hearty Lunch at Cafe 26
No getaway is complete without delicious food, and Cafe 26 is the place to start your day. This cute spot offers friendly service and an extensive breakfast menu. Sara and I were blown away by the crepes drizzled in hollandaise sauce.
If crepes aren’t your thing, don’t worry—Benedicts, pancakes, and omelets are all on the menu.

Need more places that are great for a girlfriend’s road trip? How about the Perfect North Michigan itinerary?
Milton Family Restaurant
You can’t go wrong with Milton Family Restaurant for lunch or dinner. Their spaghetti and meatballs tasted just like my grandma made them, and the toasted garlic bread and grated parmesan cheese were the perfect complements.
Sara opted for a burger and fries, and we both loved the friendly, community feel of the place.

Fredrick’s Supper Club is another fantastic option, offering a modern touch and an elegant atmosphere. The menu boasts tasty steak and snow crab legs, served with potato pancakes. The bread and flavored, whipped butter that starts your meal is a delightful touch.
If seafood is your thing, the fresh fish comes highly recommended.

If you’d like to know more about Wisconsin and its supper clubs, check out the ‘100 Things to Do in Wisconsin Before You Die’ book by my friend Dannelle Gay, The Traveling Cheesehead.
Sharla’s Coffee
No trip is complete without a great coffee spot, and Sharla’s Coffee is a must-visit. The menu offers every tea, soda, and coffee option imaginable. The owner hails from Portland, Oregon, bringing a touch of that city’s renowned coffee culture to Milton.
And check out Sharla’s Bake Shop in the heart of Goodrich Square for a delicious and satisfying sweet treat.

Bonus Things to Do in Milton
Start your day with a stroll through downtown Milton, where you’ll find South Goodrich Park. This lovely park features a kid’s splash pad and beautiful flowers. The streets are clean, and you’ll notice the strong sense of community pride.

For more outdoor beauty, head to Royce Dallman County Park for views of the Glacial Heritage Area and Lake Koshkonong. It’s a picturesque spot with plenty of picnic tables and scenic views.
The drive along Route 35’s “Rustic Road” is a treat, offering a picturesque route to the park.

Whether sipping wine at Timber Hill, shopping at Red Rooster, or hiking the Ice Age Trail, Milton offers a superb blend of relaxation and adventure. Gather your besties and embark on a getaway to Milton that will be sure to make your Instagram story.
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