A Girlfriends’ Getaway to Milton, WI

Check out this adorable small town you'll want to plan a girlfriends' getaway to...and Milton, Wisconsin.

Milton, Wisconsin is a small town that neighbors Janesville. At one time, it was a booming town with the highway running right through it, until the bypass came along. Years later, Milton is a charming destination that is off-the-beaten-path with several neat things to see and do. I found it just perfect for a road trip with my frequent travel companion and friend, Sara of Travel with Sara. Here is your guide to a girlfriends’ getaway to Milton, WI, including what to see and do while you are there.


The Wineries

Timber Hill Winery is a festive place with indoor/outdoor seating, live music, and a plethora of other events, ranging from corn hole and book club to trivia. A five wine sampling will run you $5 and there is a small menu to order complimentary food to go with your wines. My favorite was the Big Buck Blueberry.

Sara and I chowed down on the onion dip and house-made chips, which I highly recommend. They also serve quite a few pizza options. Timber Hill is a really fun place to be and has a lively, young crowd feel.


A second place to enjoy a wine and chocolate, wine and cheese, or painting class (wine glasses) is Northleaf Winery. I enjoyed Northleaf’s tasting room—which was laid-back and had a pleasant vibe, plus there are all sorts of cool things to check out. There were bottled wines for sale, wine accessories, gourmet foods, “stocking stuffers”, and more. The award-winning bottles and medals were on display and caught my interest. Sara and I were very relaxed there and could have spent hours just enjoying wine and conversation.

My favorite wine at Northleaf was the Blueberry Rare Blend. We did the wine and chocolate pairing, which included six samples and quite a decent amount of win for around $15. Northleaf not only serves house-made candies, but they paired them really well with the wines we were sampling.

Fun Fact: Northleaf can ship to 39 states.



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.

If shopping isn’t your thing, and you want to get outdoors, consider hiking the Ice Age Trail. The trail head is on E. Storrs Lake Road. This path passes through the woods where Abraham Lincoln camped about 150 years ago.


One of the best places to discover Underground Railroad history in Wisconsin is at the Milton House Museum, once the focal point of the town. Here, you will see where the Goodrich family resided and made their wealth by offering rooms for rent to those on the busy nearby highways. There is documentation that they aided in helping freedom seeker Andrew Pratt find his way to safety via rock tunnels on their property.


Not only will you hear the story about the wealthy family and fugitive man, but also have a chance to see furnishings from the family and time period, and walk through the pathway where Pratt hid for several days. It is riveting and a great piece of history that continues to have people seeking for more.


Bountiful Breakfast and Hearty Lunch

Cafe 26 is an excellent stop for breakfast before heading out of town. Sara and I chowed down on the delicious dishes from this friendly and cute cafe. I had a breakfast crepe drizzled with hollandaise, which was so good that I nearly licked the plate clean.

Cafe 26 has an excellent menu with Benedicts, biscuits and gravy, many omelets, pancakes, and dozens of other breakfast entrees. The Chicken Fajita and Cordon Blue Skillets had me intrigued.


For lunch, we took a break from our shopping and sightseeing in downtown Milton to visit the Milton Family Restaurant. There’s something here for every taste and my Spaghetti and Meatballs was really good, the kind my grandma used to make. I even had perfectly toasted garlic bread and a side of grated parmesan cheese to complete my dish. 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

You must experience a Wisconsin Supper Club while you are in the area, and you can do just that at Fredrick’s Supper Club on Merchant Row. Fredrick’s has a modern, elegant feel and a really pretty bar area. The dining room was full of people laughing and having a good time over their dinners. Bread and a flavored, whipped butter were brought to the table when our waitress first arrived.

I ordered steak and snow crab legs, with potato pancakes on the side. Thanks to Fredrick’s for supplying both applesauce and sour cream to go with the tasty little side item— just how I like them. A friend had the fresh fish with a baked potato, which she raved about. All in all, my first supper club experience was a success and I can’t wait to try more of them.

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 downtown and stroll around the streets. The South Goodrich Park is a fabulous feature, complete with a kid’s splash pad and lovely flowers. The streets 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.

Then, we headed to Sharla’s for a fresh, strong coffee. Sharla’s has a great menu with every tea, soda, and coffee option you can think of. The owner is from Portland, Oregon, so you know the owner knows coffee.

I found Sharla’s a bit confusing that you park in the lot, where a food truck sits but wasn’t open at the time, but the main entrance is in the front of the building, but we found it, so that is all that matters.


A Unique Place to Stay

A special feature of Northleaf Winery is that they have a guest house for rent across the parking lot from the winery. It is upstairs in a historic house, and has four bedrooms, a great jacuzzi tub, separate kitchen and dining room, plus a comfortable and functional living room. Sara and I were very comfortable here and loved how close it was to everything. You could bring a few girlfriends on this getaway and all of you fit at here comfortably.


Check out more of our Midwest posts:

Midwestern Cities You Must Visit

Fun Things to Do in South Bend

A Rural Kansas Road Trip

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