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A Fun Girlfriends’ Getaway to Milton, WI

A Fun Girlfriends’ Getaway to Milton, WI

If you’re looking for a hidden gem to add to your travel bucket list, make sure to put Milton on it! This quaint and charming town is packed full of surprises and unique experiences, just waiting for you to discover them. A girlfriends’ getaway to Milton, WI, is also a suggestion, which is how I explored it.

Despite being bypassed by the highway, Milton has managed to retain its charm and appeal as a must-visit destination. Whether you’re flying solo or prefer to bring along a companion or two, Milton has something for everyone to enjoy.


Bond with your besties over the many fun and exciting things to see and do in Milton, which we have listed in an easy to follow fashion for you.

The Lively Timber Hill Winery

If you’re looking for a lively atmosphere and good wine, look no further than Timber Hill Winery. This festive wine spot offers both indoor and outdoor seating, complete with live music and a variety of events to keep you entertained.


From corn hole and book clubs to trivia, there’s always something fun going on at Timber Hill. And for just $5, you can sample five different wines, a great price and way to sample the goods. Big Buck Blueberry was my top pick.

Timber Hill Winery also has food to complement your experience. My friend, Sara, and I couldn’t get enough of the onion dip and house-made chips. But the best part about Timber Hill was the fun, energetic vibe that attracts a youthful crowd.


The Laid-back Northleaf Winery

A second place to enjoy a wine & chocolate, wine & cheese, or a fun painting class (wine glasses) is Northleaf Winery The atmosphere is chill and inviting, making it the perfect spot to unwind and take in all the interesting trinkets they have on display.


From bottles of wine and accessories to gourmet snacks and unique stocking stuffers, there’s no shortage of goodies to check out. They’ve even earned impressive awards for their delicious vino, which adds to the appeal.

During my visit, I tried the Blueberry Rare Blend, and I have to say, it was definitely a standout. A wine and chocolate pairing also proved to be a sweet highlight, with six different confectionery options that perfectly complemented each sample.

The best part? My friend and I were so relaxed we could have easily spent hours chatting and sipping.

Fun Fact: Northleaf can ship to 39 states.


Shopping on Your Girlfriends’ Getaway to Milton

You’ll find a few darling little shops around Milton, with one-of-a-kind treasures. Hattie & Elsie was one of them. The store is absolutely gorgeous with decorative housewares, gifts, and fun accessories.

I bought a darling camper tea light holder which will be perfect for outdoor picnics in the RV parks.


Sara and I tried on hats for an Instagram picture, and she ended buying the one she is wearing in the photo. I’m now seeing her in it all over the country.


Another fun shop was Red Rooster inside the Old Junction Mill, a 150-year old renovated old feed mill. This space is amazing, chock full of goodies and nearly 50 artisan contributors for a two-story venue that will take you about an hour or more to see thoroughly.

I loved the pet gifts and jewelry selections, but I went home with a Wisconsin t-shirt.


The Ice Age Trail

How about an adventure that doesn’t involve hitting the shops? Lace up your hiking boots and hit the Ice Age Trail! This picturesque path is the perfect way to soak up some fresh air and explore the great outdoors.

Plus, it boasts some serious historical cred – you’ll trek through the very same woods where Honest Abe Lincoln once camped over a century ago. Ready to answer the call of the wild? Head to the trailhead, located on E. Storrs Lake Road, and let the adventure begin!


Get ready to step back in time at the Milton House Museum, one of the top spots to explore the fascinating history of the Underground Railroad in Wisconsin. This historic museum was once the busiest spot in town, where the Goodrich family made their fortune by offering rooms for rent to those seeking refuge on the nearby highways.

Through the rock tunnels on their property, fugitive Andrew Pratt found his way to freedom with the help of this brave family.


But that’s not all – when you visit the Milton House Museum, you’ll get to experience so much more. You’ll have the chance to see furnishings from the time period and walk through the same pathway that Pratt once hid in for days.

The compelling museum is bursting with incredible stories and meaningful artifacts that remind us of this important piece of our history.


Breakfast or Hearty Lunch at Cafe 26

Looking for a breakfast spot that’s both delicious, cute, and has a friendly staff? Look no further than Cafe 26. My friend Sara and I stopped by and were blown away by the amazing crepes drizzled in hollandaise sauce.

But if you’re looking for something different, don’t worry – Cafe 26 has an extensive menu filled with breakfast classics like Benedicts, pancakes, and omelets to satisfy any craving.


Milton Family Restaurant

If you’re around for lunch or dinner, try the Milton Family Restaurant’s spaghetti and meatballs. They tasted just like my grandma made them! Plus, the toasted garlic bread and grated parmesan cheese on the side were the perfect complements. Sara chose a burger and fries.

I liked that Milton Family Restaurant was probably THE place to be in town, where everybody knows you and you can find a friendly face in the crowd at any time. We were glad we stopped.


Supper Club Dining at Fredrick’s

Fredrick’s Supper Club, on Merchant Row, is a dinner spot with a modern touch and an elegant atmosphere. There was a bustling crowd, sharing laughter and good times over delicious dinners. An added bonus is the bread and flavored, whipped butter that’s brought to your table upon arrival.


I can personally vouch for the tasty steak and snow crab legs, served with potato pancakes, and with your choice of applesauce or sour cream. If seafood is your thing, my friend raves about Fredrick’s fresh fish.

This was my first supper club experience, but thanks to Fredrick’s, it won’t be my last. Get ready to indulge in a true Wisconsin tradition that’ll keep you coming back for more.

Fun Fact: Let’s talk for just a minute though about the homemade blue cheese dressing, which was insanely good.


Bonus Things in Milton

When Sara and I arrived in Milton, the first thing we did was park in downtown Milton and stroll the streets. The South Goodrich Park is a fabulous feature, complete with a kid’s splash pad and lovely flowers.

The streets of Milton are very clean and you notice the sense of community and pride immediately.


We drove out to Royce Dallman County Park for views of the Glacial Heritage Area and Lake Koshkonong. It’s really beautiful out there, and plenty of picnic tables and places to enjoy sitting around, soaking up the scenery.

The road that brought us here, Route 35’s “Rustic Road” was picturesque and a great drive.


Sharla’s Coffee

If you’re a coffee fan or aficionado, then Sharla’s is definitely worth a visit. They’ve got an awesome menu chock-full of every tea, soda, and coffee option you can imagine. And if that’s not enough to entice you, the owner hails from Portland, Oregon, a city known for its coffee culture.

Although the parking situation might be a little confusing, don’t let that dissuade you from checking out this hidden gem.


A Unique Stay at Northleaf Winery Guest House

Experience a unique stay at Northleaf Winery’s charming guest house located just a stone’s throw away from the winery. Nestled upstairs in a beautiful historic house, this gem boasts four cozy bedrooms, a lavish jacuzzi tub for some R&R, a well-equipped kitchen, and an elegant dining room to satisfy your culinary cravings.


Unwind and relax in the comfortable and functional living room while sipping on your favorite glass of wine. The guest house is perfect for a girl’s getaway to Milton – and space is not an issue here. You’ll love how convenient it is to everything in the area.


Check out more of our Midwest posts:

Midwestern Cities You Must Visit

A Rural Kansas Road Trip

Visiting Alpena, Michigan

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