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! And where are we headed this time? We’re mapping out the perfect Midwest gay road trip that’ll have you falling head-over-heels for America’s heartland. Pack your crew, crank the playlist, and prepare for scenic routes, hidden gems, and gay-friendly destinations that prove the Midwest doesn’t mess around when it comes to hospitality.
Fall has arrived, darling! Summer’s sweltering nights are giving way to crisp days and cozy evenings perfect for exploring. While those beach memories are still fresh, it’s time for vineyard tours, bonfires, and foliage drives with your favorite people.
Destination: Wisconsin’s LGBTQ+ Scene
Chicago might be “the city” around these parts, but here’s the thing about the Midwest — it skips the pretentious big-city games. No waiting three days for a text back here. This region forgot Americans are supposed to have attitude problems, and honestly? We’re here for it.
The Route
- From Chicago: 90 minutes north via I-94
- From Minneapolis: 5 hours east on I-94
- Expect flat farmland from Chicago, rolling hills from the Twin Cities
Your Wisconsin Road Trip Itinerary
Leave Chicago’s hustle behind and discover why Wisconsin offers way more than cheese and cows (though we’ll get plenty of both). Once you hit that 94 speed limit, you’ll cruise past endless corn fields and farm stands, but trust us—the good stuff’s coming.
First Stop: Apple Holler & Mars’ Cheese Castle
Cross into Wisconsin and immediately hit Apple Holler in Sturtevant for their legendary apple pie. Then detour to Mars’ Cheese Castle in Kenosha because cheese curds are basically a Midwest road trip requirement.
Milwaukee: Your Gay Travel Destination
Thirty minutes later, you’re in Milwaukee. Plug “Walker’s Point” or “Downtown” into your GPS—that’s where the gayborhood lives, and it’s fabulous.
Cultural Stop: The Milwaukee Art Museum showcases 25,000 works in an architectural stunner designed by James Shields. The building itself is art, offering killer Lake Michigan views.
Nightlife Scene: This German-settled city knows how to party. Hit up:
- Kruz Bar, LaCage, and This is It! (celebrating 50 years of fabulousness)
- Harbor Room for the leather crowd
- Woody’s for game day vibes
Dining: Grab coffee at Alterra or camp it up at Hamburger Mary’s. For authentic German fare, Mader’s downtown serves old-world flavors that’ll make you understand why people settled here.
Ready to explore the Wisconsin’s queer-friendly side? This Midwest gay road trip proves America’s heartland has serious heart—and knows how to show LGBTQ+ travelers a damn good time.
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