15 Best Road Trips From Milwaukee, Wisconsin

road trips from milwaukee
Collins
Collins 
Updated

Sitting on the shores of Lake Michigan is one of the most beautiful cities in the country, Milwaukee. The region has a rich history and culture. Famous for its fascinating breweries and exciting baseball league, this growing city expands daily to accommodate the increasing number of attractions and of course, visitors. Businesses, cultural centers, and even relaxing spa hotels and unique themed hotels are springing up throughout the city. With remarkable architectural buildings, museums, beer baron homes, incredible breweries, gorgeous gardens and parks, and of course, exciting summer festivals, this magnificent city is a place you want to be. As much as there is a lot to do and see in this location, sometimes you may want a change in scenery. Luckily, there are amazing places and things to see within a few hours of driving from Milwaukee. So to enjoy that much-needed change of scenery, check out the best road trips from Milwaukee, Wisconsin.

1. Somerset, KY

barn in Somerset, KY
Source: Photo by Flickr user guidedbynoises used under CC BY-ND 2.0

Home to the fourth-largest recreational lake in the country, Somerset is a relatively popular destination among visitors. Located in Kentucky, the city is a calm yet lively place to spend some time relaxing with friends and family. With a sunny and inviting weather, the location boasts having a lush forested landscape, family parks, a family fun center, several movie theaters, and other entertainment areas. Somerset sits at a distance of 518.9 miles (835 kilometers) from Milwaukee, with an estimated drive time of 8 hours and 12 minutes.

See Somerset in an Outdoorsy RV

2. Franklin, TN

Autograph Bridge
Source: Photo by Flickr user Larry Yeiser used under CC BY-ND 2.0

Located about 588 miles (946 kilometers) from Milwaukee, Franklin is an exciting place to see. The city is calm and historical, with a lot of things to experience. Franklin has fun activities, and some fantastic features of the place include its beautiful vineyards where you can go wine tasting, fancy restaurants, music festivals, a year-round farmers’ market, a historic ancient trail drive, a theater, and so much more. It takes just over eight hours to get to Franklin from Milwaukee.

Book your Milwaukee RV here

3. Jasper, AR

Jasper, Ozarks 7/6/20
Source: Photo by Flickr user Sharon Mollerus used under CC BY 2.0

If you’re looking for long drives and a weekend getaway from Milwaukee, then the picturesque and scenic Jasper, AR, might be right up your alley. This exceptional town is surrounded by natural beauty. The little town of Jasper has received several accolades for its serene and beautiful atmosphere. Aside from a lot of exciting spots for outdoor activities like hiking, biking, rock climbing, mountain biking, and horseback riding, the region also has pristine points for water activities like canoeing, fishing, etc. if you drive into the town at the right time, you’d get a chance to join in the festivities of Buffalo River Elk Festival. Note that Jasper is 676 miles (1,087 kilometers) from Milwaukee.

Rent an RV for your Jasper adventures!

4. El Dorado, AR

ChrisLitherlandElDorado
Source: Photo by Wikimedia Commons user Chris Litherland used under CC BY-SA 3.0

A town known for its oil boom back in the 1920s, El Dorado is a beautiful place to explore. The drive from Milwaukee to El Dorado covers about 857 miles (1,379 kilometers) and takes just over 12 hours. What’s stunning about the town is its beautifully built 1930s-style buildings and its bubbling downtown area filled with stores and restaurants. With more than enough cultural centers and galleries, this destination is no doubt worth the trip!

See the best of El Dorado from your RVshare trailer

5. Hodgenville, KY

Abe Lincoln birthplace
Source: Photo by Flickr user Brent Moore used under CC BY 2.0

Hodgenville, located in central Kentucky, is another exciting place you can’t get enough of. This unique city sits along the North Fork of Nolin River, about 448 miles (720 kilometers) from Milwaukee, and it’s famous for being the birthplace of the 16th president of the United States, Abraham Lincoln. The location offers an eclectic mix of rich history, cultural heritage, several different events and fairs, trendy shops, and cool restaurants and bars. The charming place takes just over six hours to get to from Milwaukee.

Milwaukee to Hodgenville in an Outdoorsy RV!

6. Gatlinburg, TN

Gatlinburg, TN 37738, USA - panoramio (9)
Source: Photo by Wikimedia Commons user Evan Nichols (Vir... used under CC BY 3.0

If you love outdoor fun but would like a change of pace from outdoor activities in Milwaukee, then Gatlinburg has got you covered. Situated in Tennessee, about 676 miles (1,087 kilometers) from Milwaukee, a road trip to this city takes about 10 hours. Aside from giving you ample time to bond with friends or family during the journey, a road trip to Gatlinburg will make it worth your while. Enjoy exciting outdoor adventure opportunities as well as several other exciting side attractions, including shopping in chic boutiques for unique items such as woodcrafts and artworks, admiring art galleries, joining moonshine tastings, and so much more.

Check out these cool Milwaukee trailers and motorhomes!

7. Van Buren, AR

Anheuser-Busch Building, Van Buren, Arkansas
Source: Photo by Wikimedia Commons user doug_wertman used under CC BY 2.0

Historic and remarkable, Van Buren is a haven for tourists looking to get their hands on difficult-to-find collectibles, unique gifts, local Ozark crafts, authentic local art, and so much more. Although it takes almost half a day of driving to get there, this destination makes up for the long drive by offering you many fascinating historical attractions, antique shops, art galleries, and of course, remarkable places to enjoy exclusive dining. At approximately 781 miles (1,256 kilometers) from Milwaukee, it is a great place to enjoy a wide range of recreational activities.

Rent a trailer to see Van Buren - click to book!

8. Bardstown, KY

Willet Distillery (Bardstown, Kentucky)
Source: Photo by Wikimedia Commons user Nheyob used under CC BY-SA 4.0

Having once been described as the Most Beautiful Small Town in America, Bardstown, Kentucky, offers so many interesting things to do. With a six-hour road trip covering the 433 miles (696 kilometers) between Milwaukee and Bardstown, you get to enjoy a variety of exquisite experiences along the way. As the second-oldest city in Kentucky, Bardstown is loaded with historical places to visit, as well as trendy shops, fascinating distilleries, scenic landscapes, and a unique Southern charm to relish and enjoy.

Rent your Milwaukee trailer or motorhome here

9. Siloam Springs, AR

City Park, Siloam Springs, AR 002
Source: Photo by Wikimedia Commons user Brandonrush used under CC BY-SA 4.0

Popular for its natural beauty and pristine, lush landscape, Siloam Springs is an attractive place. The city sits at a distance of 722 miles (1,161 kilometers) from Milwaukee and has a lot of parks, walking tours, and several places to relax in. With playgrounds for kids, picnic areas, an aquatic park, boutiques, antique shops, fine restaurants, coffee shops, golf courses, and historic buildings, Siloam Springs is an excellent place to visit and spend quality time with friends or family members.

Click to rent an Outdoorsy RV for your Siloam Springs getaway

10. Cleveland, TN

Old Factory, Cleveland Tennessee
Source: Photo by Flickr user Jeff Jackson used under CC BY-ND 2.0

Cleaveland is the perfect place to take time off from the big city and enjoy some relaxing small-town activities. It is situated at about 717 miles (1,154 kilometers) or a 10-hour drive from Milwaukee. Venture on this road trip to enjoy Cleaveland’s authentic experiences. Cleveland offers several outdoor activities, including cave exploration, whitewater rafting, ziplining, wine tasting, and a lot of other fun watersports. With its beautiful vineyards, great restaurants, delicious street-food stands, and lots of museums, you will surely enjoy your getaway to this destination.

Explore Cleveland with an RVshare motorhome or trailer

11. Gurnee, IL

Great America, August 1976
Source: Photo by Flickr user Alan Light used under CC BY 2.0

This village in Illinois is the shortest road trip from Milwaukee. The drive only takes about 49 min and is about 50.6 mi or (81km) via I-94 W from the heart of Milwaukee. Gurnee has amazing attractions perfect for everyone - families, friends, couples, and solo travelers will surely have an enjoyable trip here. With attractions like Great Wolf Lodge Water Park, Six Flags, and Hinkston Park - an indoor, state-of-the-art sports facility - you’ll definitely have a full day of adventure ahead of you.

12. Kohler, WI

Whistling Straits Clubhouse - Kohler, Wisconsin
Source: Photo by Flickr user Dan Perry used under CC BY 2.0

This small-town village situated just 54 minutes north of Milwaukee is about 55.5 miles (89 km) away. Kohler, WI, is perfect for golf enthusiasts as it has two top-notch golf courses, namely Whistling Straits Golf Course, Blackwolf Run, and a golf simulation center, Kohler Swing Studio & Golf Shop. Whether you enjoy actual golf outdoors or would like to try your hand at virtual golf, Kohler is the place to be. Other attractions like The Waelderhaus, a historic architectural building, and The Blind Horse Winery are also in the area.

13. Chicago, IL

Chicago-illinois-skyline-skyscrapers-161963
Source: Photo by Wikimedia Commons user quinntheislander used under CC0

Chicago, IL is one of the best cities to drive to from Milwaukee, in fact, it only takes and 1 hour and 30 minutes to get there. Just 93.1 mi or 150 km via I-94 W from Milwaukee, Chicago is one of the largest cities in the US. There are lots to do here, from discovering the downtown Chicago area, Magnificent Mile, or visiting Navy Pier, this city is an ideal weekend getaway for everyone. The Windy City is known for its rich history, skyscrapers, and architecture, as well as amazing food options. So if you want a change of scenery, then Chicago is definitely a top choice.

14. Madison, AL

Downtown Madison, Alabama
Source: Photo by Flickr user Shannon McGee used under CC BY-SA 2.0

If you’re looking for a long drive then this road trip is for you. Take a week off work and discover the joys of interstate road trips. From Wisconsin to Alabama, it takes about a 14-hour drive, and you’d pass by 4 states, with so much to see and discover. From Wisconsin, you drive past Illinois, Indiana, Kentucky, and Tennessee before you reach Alabama. Madison, in particular, is a beautiful city with a small-town vibe where you’ll experience the best southern hospitality and some of the top family-friendly activities. Visit hiking areas like Rainbow Nature Reserve and beautiful parks like Dublin Park - these places are perfect for kids and parents alike. Madison is a quaint city that’s a perfect destination for a road trip.

15. Oshkosh, NE

Oshkosh, Nebraska Main St 3
Source: Photo by Wikimedia Commons user Ammodramus used under PUBLIC DOMAIN

Nearly a 13-hour drive, Oshkosh, Nebraska is west of Wisconsin and is a vibrant city with much to offer, especially to those who want to escape city life. Its rural charm is definitely worth a visit, and if you’d like to go for a road trip you won’t regret, then visit Oshkosh. Enjoy fishing or hunting in Blue Creek Lodge, or stay in an RV and camp in Oregon Trail Campsite. You can also visit the historic Garden County Historical Society. Don’t miss these top attractions, escape the busyness of the city, take that road trip from Milwaukee to see the wonderful countryside of Oshkosh, NE, for that much-needed retreat.

Visit the most amazing places on your road trip from Milwaukee

Milwaukee has a lot of beautiful places to see, places to eat, and things to do for everyone. However, one of the fun things to do when visiting is to take a road trip to the exciting neighboring cities. And with this list of the best road trips from Milwaukee, Wisconsin, you’re ensured a wonderful time.

Frequently asked questions about the best road trips from Milwaukee, Wisconsin

1. What are great weekend getaways from Milwaukee with friends?

Some of the best weekend getaways from Milwaukee with friends would be road trips to Somerset, KY, Siloam Springs, AR, Gurnee, IL, and Chicago, IL. Have fun and celebrate with your friends by driving down to these cities.

2. What are cities within eight hours of Milwaukee?

If you’re looking for cities within eight or fewer hours of Milwaukee, then these cities are for you: Bardstown, KY, only takes six hours from Milwaukee, while Kohler, WI, Gurnee, IL, and Chicago, IL are all within a two-hour drive.

3. What are the best 10-hour drives from Milwaukee?

The two best 10-hour drives from Milwaukee are road trips to Gatlinburg, TN, and Cleveland, TN. Franklin, TN takes about 10 hours as well. Visit these cities to enjoy great music festivals, wine, and shopping.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

Get Trip101 in your inbox

Unsubscribe in one click. See our privacy policy for more information on how we use your data

Colins is a quiet individual who always tries to find the meaning and beauty of things around his environment. This passion has led him to begin his journey in photography and hiking nature...Read more

 Want to contribute as a Local Expert?
Explore Milwaukee
Looking for accommodation?
Good things are meant to be shared!