Hit the Road, Jack: Road Trip Through Midwest

At the Milwaukee Art Museum

All this month, we’re taking you on a road trip. Bid your city and your stresses adieu. Grab some friends, jump in the car and take the scenic route with us. Find brilliant little stops, surprises tucked away, and tips to make the road trip experience complete. Do you already have a favorite road trip that you took? Let us know!

Hard to believe it but fall is here! Hot and steamy summer nights make way for colorful days and cozy evenings.

Fall follows summer, meaning beach memories and tan lines remain fresh, but you’re ready for vineyard tours, bonfires, and foliage drives with your special someone. Now’s the perfect time to plan a long weekend or week — you deserve it! — exploring a gay-friendly city and its surrounding Technicolor countryside towns.


Midwest! In this part of the country, Chicago is “the city,” but one that largely puts aside those big-city rules. In dating terms, the Midwest doesn’t wait two days to call you back after a date. Friendly and inviting, this part of the country forgot that Americans are supposed to have an attitude.


90 minutes on I-94 North via I-90 North from Chicago. About 5 hours East on 1-94 from Minneapolis. Gear up for some flat land when coming from Chicago, but the trip from the Twin Cities might be a little more on the hilly side.

The Itinerary:

It’s time to escape Midwest’s biggest metropolis, Chicago, and head to the Dairy State for more than just cows and farms. Once out of the city and hitting the speed limit on I-94, you will undoubtedly pass corn fields and farm hands aplenty. However, 45 minutes later, Wisconsin signage will welcome you and that’s when the fun starts.

Once you cross the boarder your first stop should be at Apple Holler, in Sturtevant, WI, for a delicious home-baked apple pie or apple butter and a detour to nearby Mars’ Cheese Castle, in Kenosha, WI, for cheese curds is perfect start to ticking off your mid-west eats from your road-trip to-do list.

Driving 30 more minutes and you’re in Milwaukee and you’ll want to input Walker’s Point or Downtown into your navigation for the gayborhood. We couldn’t resist a trip to the Milwaukee Art Museum and any one of its 25,000 works of art in a dynamically designed building by local architect, James Shields. The building itself is a work of art as it affords stunning views of Lake Michigan.

Beers and queers are on the menu at this German settled town’s gay neighborhood with drinks at Kruz Bar, LaCage and This is It!, which is celebrating its 48th year. Harbor Room leans toward the leather crowd, where Woody’s is best to catch any college or NFL game that you could imagine.

If you’re hungry, Alterra and Hamburger Mary’s are good for a bite, but we might sample some more traditional old world German fare at Mader’s, near downtown.


Staying Fit While on the Road

Skip the Chips and Dip for These Healthiest Road Trip Snacks

Find Healthy Food on Your Road Trip (There’s an App for That)

Drive Out of Your Comfort Zone: Road Trip Through New England

Drive Out of Your Comfort Zone: Road Trip Through Northern California

Drive Out of Your Comfort Zone: If Dolly Can do It, So Can We!

Drive Out of Your Comfort Zone: Road Trip Through the Mid-Atlantic

Hit the Road, Jack: Making a Run from the Border to the Desert

Photo by Flickr user David Hilowitz used under the Creative Commons Attribution license