5 Great Day Trips From Milwaukee | Milwaukee Magazine

Ask MilMag: Where Should I Go for a Day Trip?

In this series, Milwaukee Magazine staffers answer questions about the city, share cherished memories, give unsolicited advice and crack the occasional dumb joke.

1. Chicago

BRIANNA SCHUBERT, ASSOCIATE DIGITAL EDITOR

I love getting a train ticket down to Chicago, first because it’s fun to ride the train and second because it’s a hassle-free way to get there without traffic and third it’s a great place to spend a day. When I’m there, I like to go to the Art Institute of Chicago, grab some food at a new restaurant and walk along the lake. It’s a fun way to get a dose of big city without having to leave the midwest!

Chicago; Photo by Getty Images

2. Sheboygan

CHRIS DROSNER, EXECUTIVE EDITOR

I’m braving the I-43 construction to head to Sheboygan for the day, and this is mostly about replicating Ann Christenson’s Shevegas leg of her Foodie Road Trip feature last summer. I’d start with lunch (I get a slow start, OK?) at The Northwestern House, telling myself not to overdo with the casual fare because we’ve got big plans for dinner. Then it’s off to 3 Sheeps Brewing, one of the state’s best breweries and an awesome taproom experience, with a good vibe, great beer and a cool golf simulator. Beerwise, have something light, sure (their excellent Oktoberfest, just tapped, is only 5.5% ABV), but make sure to try one of 3 Sheeps’ big, dark beers; they’re outstanding almost without exception. I’m spending some time on the lakefront and just driving around the city’s neighborhoods – it’s a great way to get a feel for a place beyond the thoroughfares – before pulling into Stefano’s Trattoria for dinner. I trust Ann in all matters gastronomic, and her praises of this restaurant… yeah, it’s a gotta.


It’s time to pick your Milwaukee favorites for the year!

 

3. Lake Geneva

ARCHER PARQUETTE, MANAGING EDITOR

Before I was the old, decrepit sack of regrets I am today, I was once a young, hopeful high schooler. And that young hopeful high schooler had his senior year retreat at Lake Geneva. And during that retreat, he allegedly snuck out of the retreat dorm at midnight with some fellas to go on a pointless, but unbelievably fun, Burger King run. And the memory of those illicit Whoppers remains cherished to this day. The nostalgia alone is powerful enough to keep me returning to Lake Geneva on many a day trip. But the scenic lake, shoreline walking path, Topsy Turvy Brewing, Sopra Bistro, and other attractions in the charming little resort city don’t hurt, either.

Photo courtesy of Visit Lake Geneva

4. Madison

ALLI WATTERS, DIGITAL & CULTURE EDITOR

Go on a Saturday so that you can hit the farmers market. Pick up a loaf of Stella’s Spicy Cheese Bread (you won’t regret it) then take a lap around the Capitol to peruse the fresh produce and maybe get a beautiful bouquet of fresh cut flowers. From there, I would recommend trekking up State Street to the Memorial Union Terrace where you can enjoy a pitcher outside with beautiful views of the lake. In the evening, get your tickets to a Flamingos soccer game. The team is great and the games at Breese Stevens Field are a ton of fun to watch. The after party should be at Vintage.

Photo by Getty Images

5. La Crosse

SOPHIE YUFA, DESIGNER

I would drive up to Grandad Bluff in La Crosse for a hike and admire the great views! Another worthwhile point of interest to check out would be the Shrine of Our Lady Guadalupe (be prepared for a steep trek on foot to the top). For breakfast or early lunch, I highly recommend visiting The Breakfast Club & Pub, inspired by (you guessed it!) John Hughe’s coming-of-age 1985 comedy-drama film. Their chicken waffles are superb. 

La Crosse; Photo by Colin Stouffer, courtesy of Explore La Crosse