Milwaukee, Wisconsin’s largest city, is bustling with over half a million residents, a buzzing beer culture, vibrant festivals, and an impressive art scene. But when you’re in the mood for a change of pace, these nearby gateways from Milwaukee offer the perfect escape.
Within a 200-mile radius, you’ll find charming towns in Wisconsin, Iowa, and Illinois that boast lakeside views, cozy main streets, delicious restaurants, and plenty of outdoor adventure. These gateways from Milwaukee are ideal for a quick weekend getaway, sparing you the hassle of long road trips while still offering scenic beauty and a refreshing break.
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8 Road Trips from Milwaukee That Will Make You Pack Your Bags Now
1. Lake Geneva
Just 50 miles from Milwaukee and a short hop from the Illinois border, Lake Geneva serves as the ultimate Midwest lake retreat. Famous for its luxury resorts, charming 19th-century mansions, and boutique-filled downtown, Lakeside Geneva is a must-visit destination near Milwaukee Wisconsin. At its heart lies Geneva Lake, the state’s second-largest spring-fed jewel, offering stunning views and a tranquil escape perfect for relaxation and lakeside adventures. Hop on a Lake Geneva Cruise Line boat for a peek at the elegant Victorian homes along the shoreline.
Prefer to stay on land? Hike the scenic 21-mile Lake Geneva Shore Path or relax at Riviera Beach near downtown. Hungry? The area offers local farm-to-table favorites like Simple, and while Milwaukee boasts some of the best Milwaukee restaurants, you don’t have to venture far to enjoy amazing food. Next Door Pub dishes up some of the best pizza you’ll ever taste, right here in Lake Geneva.
2. 120 Miles from Milwaukee: Green Bay Beyond the Magnificent Mile!
Green Bay may be famous for the Green Bay Packers, and yes, a Lambeau Field Stadium Tour is a must-do, but this lakeside gateway from Milwaukee has so much more to offer. Right next to the stadium is the lively Titletown district, where year-round fun awaits with restaurants, shops, a weekly night market, plus seasonal sledding and ice-skating.
For nature lovers, the 535-acre Bay Beach Wildlife Sanctuary is home to rehabbed animals like owls and foxes. Nearby, the Bay Beach Amusement Park offers classic carnival vibes with cotton candy and a mini train ride. And don’t miss the Green Bay Botanical Garden, where you can stroll 47 acres filled with over 85,000 stunning plants. Green Bay truly offers the perfect gateway from Milwaukee for sports fans, nature enthusiasts, and families alike!
3. Baraboo is the Place You’ll Wish You Knew Sooner!
While Milwaukee Wisconsin Dells often steals the spotlight, Baraboo is a hidden gem and one of the most charming road trips from Milwaukee. Devil’s Lake State Park offers over 10,000 acres of greenery and 29 miles of hiking trails, perfect for outdoor enthusiasts. Just 15 minutes away, Parfrey’s Glen State Natural Area treats hikers to a stunning trek through sandstone boulders leading to a waterfall. Mirror Lake State Park, with its calm waters, is a peaceful retreat only 3 miles from the Dells. For a slower pace, visit New Life Lavender and Cherry Farm or pick fresh fruit at Ski-Hi Fruit Farm.
4. Chicago: Just 95 Miles Away!
When it comes to weekend getaways, it’s tough to beat a trip to Chicago, the Midwest’s largest city and a premier gateway from Milwaukee. With endless activities, you can soak up the city’s beauty on the Chicago Architecture River Cruise or explore The 606 Trail, a vibrant 2.7-mile multi-use path perfect for walking or biking. Sports fans will love taking an off-season tour of Wrigley Field, while shoppers can indulge along the famous Magnificent Mile. Don’t miss world-class attractions like the Museum of Science and Industry and the Art Institute of Chicago, both brimming with captivating exhibits.
After a day of exploring, unwind in one of Chicago’s boutique hotels, such as the chic Chicago Athletic Association Hotel or The Publishing House, where bespoke charm meets comfort.
5. 170 Miles from Milwaukee: Galena Illinois
Discover Galena Illinois, just 170 miles from Milwaukee, where you can travel back in time through its Historic District, boasting a stunning mix of architectural styles from the 1820s. Galena invites you to learn about its storied buildings while relaxing on the Galena Trolley. Stroll down the picturesque main street, home to 125 charming shops and restaurants.
Don’t miss Galena Apothecary for natural beauty products, Galena Book and Paper for your next read, or Vinny Vanucchi’s Little Italy for Nana Lu’s famous meat lasagna. For breathtaking views, hike to Horseshoe Mound, where you can see three states at once. If you’re seeking adventure, zip through the treetops with Long Hollow Canopy Tours.
6. 190 Miles from Milwaukee: Wausau
Located 190 miles from Milwaukee, Wausau is quickly becoming a sought-after destination for adventure and art lovers. Explore the breathtaking Rib Mountain State Park, renowned for its ancient rock formations dating back billions of years. Just five miles north lies Granite Peak, a local favorite ski resort featuring 60 thrilling trails across 200 skiable acres—ideal for winter enthusiasts!
If you prefer indoor attractions, visit the Leigh Yawkey Woodson Art Museum, which displays exquisite wildlife sculptures and vivid oil paintings. Downtown Wausau hosts a lively events calendar full of festivals and markets throughout the year, and don’t forget to stroll through the 300 Block, where colorful umbrellas create a playful canopy overhead, perfect for snapping Instagram-worthy photos.
7. 175 Miles from Milwaukee: Dubuque
Located 175 miles from Milwaukee, Dubuque has transformed from a historic maritime hub into a vibrant destination for families and adventure seekers. One of the top gateways from Milwaukee, the National Mississippi River Museum and Aquarium offers an engaging experience with 12 expansive aquariums and educational exhibits that kids will adore.
For outdoor enthusiasts, the Mines of Spain State Recreation Area features 15 miles of scenic hiking trails in a stunning 1,432-acre National Historic Landmark, perfect for a day of exploration. For a unique view, hop on the Fenelon Place Elevator, the world’s shortest and steepest cable car, to enjoy breathtaking tri-state vistas. Don’t miss the downtown area, where you can marvel at 40 colorful murals created by talented local and international artists.
8. 110 Miles from Milwaukee: St. Charles
Just 110 miles from Milwaukee, St. Charles is a charming historic town that invites you to unwind and soak in its delightful atmosphere. Renowned for the family-run Kane County Flea Market, which operates from March through December, it’s one of the best gateways from Milwaukee for uncovering antique furniture and collectible artwork. After indulging in some retail therapy, head downtown to enjoy live music and outdoor dining that enhances the vibrant ambiance. If you’re in the mood for entertainment, catch a show at the iconic Arcada Theatre, where a Studio 54-style dance club meets a 1920s speakeasy. To top off your nostalgic getaway, embark on a scenic Paddlewheel Riverboat trip along the picturesque Fox River.
