For the 50+ Traveler

Wisconsin’s largest city provides a lot for both visitors and locals to enjoy. From its lovely lakeside location and brewing history to its world-renowned museums and quirky festivals, Milwaukee does not disappoint. But as exciting as the city itself is, it’s also a great home base for exploring the surrounding area.

Here are some of the best day trips from Milwaukee. They’re sure to make your time in the Midwest extra special!

The coastline of Lake Michigan in Door County.

1. Door County, Wisconsin

Known as the Cape Cod of the Midwest, Wisconsin’s Door County is an excellent day destination from the Brew City. This peninsula juts out into Lake Michigan and Green Bay (the body of water, not the city). The county is the largest by size in the entire state and is home to a number of charming communities, including Ephraim, Sister Bay, Baileys Harbor, Sturgeon Bay, Egg Harbor, and Fish Creek.

There is so much to do in Door County that one could easily spend days there, so for day-tripping purposes, I suggest picking one community or area and exploring it fully. That could mean shopping and eating in Fish Creek, taking the ferry to Washington Island, or seeing the famous cows on the roof at Al Johnson’s in Sister Bay. Other fun activities include hiking at Peninsula State Park, taking the farm tour offered by the Door County Creamery, or trying out the numerous area breweries, wineries, distilleries, and cideries. Dive bar connoisseurs will love The Blue Ox on the quiet side of the peninsula, the southeastern Lake Michigan side; it opened in the 1800s as a general store and is now a kitschy watering hole. Door County is also known for its iconic cherries, and day-trippers can try them in local baked goods or consider a pick-your-own-cherries experience.

The gateway to Door County and the county seat of Sturgeon Bay is a little over 2 hours away from Milwaukee by car. The other towns along the peninsula are farther, so plan accordingly for the best day-trip experience.

The skyline of Chicago, Illinois.

2. Chicago, Illinois

The Midwest's largest city is just an hour and a half by train or car from Milwaukee. Amtrak offers service seven times a day, and since Chicago is famous for its traffic, I suggest taking the train. You’ll save money on parking, avoid the traffic, and get there faster than you would by bus, which can take 2 hours or more. Once you’ve arrived in the city, the public transit is easy to navigate, the city is quite walkable, and ride-share options abound for those who prefer a lift.

Chicago is home to amazing upscale shopping, museums, and attractions; a famous dining scene; and so much more. For a classic Chicago experience, travelers should plan to try deep-dish pizza, see the Bean in Millennium Park, and enjoy the architecture boat tour of the city. Other fun attractions include the Chicago Children’s Museum, the Shedd Aquarium, the Art Institute of Chicago, and the Field Museum of Natural History.

It’s clear that the Windy City delivers maximum day-trip potential for those starting in Milwaukee.

The Kohler Waters Spa at the American Club Resort.

3. Kohler, Wisconsin

For a charming village vibe, Kohler, Wisconsin, provides a fun day-trip experience. Plus, it’s just an hour from Milwaukee. Visitors interested in design will love the Kohler Design Center, open for daily tours during the week. There’s even a museum in the center! For those seeking to relax, Kohler is home to the renowned Kohler Waters Spa; this is one of fewer than 70 five-star spas found worldwide. The town is also known for its numerous championship golf courses. Additionally, travelers could try Kohler’s Blind Horse Restaurant & Winery, which bills itself as a Napa-style establishment.

Aerial view of Sheboygan, Wisconsin.

4. Sheboygan, Wisconsin

This option is a perfect add-on to a Kohler day trip, since it’s just 10 minutes away from the village and an hour’s drive from Milwaukee. Sheboygan, Wisconsin, sits on Lake Michigan’s stunning western shore and boasts a pretty lighthouse plus waterfront activities like kayaking, fishing, and even surfing. Visitors of all ages will love the shipwreck on the lakefront and the area’s whimsical Bookworm Gardens. Sheboygan is a dairy hot spot, too -- it’s home to the Sargento headquarters as well as the Old World Creamery. To sample some incredible cheese, check out these cheese shops in Sheboygan County.

If you’d prefer not to drive, you can take the train, but the trip will take up to 2 hours.

Aerial view of Elkhart Lake, Wisconsin.

5. Elkhart Lake, Wisconsin

Also located in Sheboygan County is the charming town of Elkhart Lake, Wisconsin, near the Kettle Moraine State Forest and the Ice Age Trail. Great eateries like the bistro-style Lake Street Café and the inventive Paddock Club make this an especially tasty destination. To get more hands-on with food, home chefs and newbies alike can visit the cooking school at the Osthoff Resort. Racing enthusiasts and history buffs can check out Road America, a famous European-style track in the area; go-karts and ATVs are available there when a race isn’t occurring. During warm weather, visitors can also enjoy lake offerings like water sports, fishing, swimming, and more. The lake is one of the deepest in the state and is known for its unbelievable turquoise spring-fed water.

Elkhart Lake is about an hour and 15 minutes from Milwaukee proper by car, which is the best option to get there.

A boat on Lake Geneva in Wisconsin.

6. Lake Geneva, Wisconsin

Another lovely resort town, Lake Geneva, Wisconsin, is a sure winner located just an hour southwest of Milwaukee. What is unique about this area is the 26-mile path that loops around the lake. Known as the Lake Geneva Shore Path, the trail offers pretty water views and is adjacent to some unbelievable mansions. The city’s tourism bureau recommends starting at the Lake Geneva Library and heading out in either direction for about a mile. This section of the shore path is paved, level, and easy to navigate. Lake Geneva is also home to numerous ice cream shops and tasty restaurants, including Sprecher's Restaurant & Pub with its famous root beer. For those interested in fun high in the sky, zip-line tours are another popular activity.

Downtown Madison, Wisconsin.

7. Madison, Wisconsin

The capital of Wisconsin, Madison, is located just an hour and a half west of Milwaukee by car. Day-trippers should make time to explore the beautiful campus of the University of Wisconsin-Madison, tour the Capitol building, and check out the famous farmers market. Summertime visitors should visit the sixth-floor museum and observation deck at the Capitol, which are only open during the warm-weather season. Madison is also known for its many festivals, so check the city’s calendar for any that might interest you. Food tours, breweries, distilleries, and wineries can also be found in the capital city.

Aerial view of Green Bay, Wisconsin.

8. Green Bay, Wisconsin

Packers fans will especially enjoy Green Bay, Wisconsin, located less than 2 hours from Milwaukee by car. The city offers numerous activities perfect for a day trip, like the Green Bay Botanical Garden, the National Railroad Museum, and Lambeau Field. Day-trippers who want to see the stadium should also be sure to stop at the adjacent Hinterland Brewery and Restaurant in the Titletown District. Besides offering handcrafted local beers, this spot has an excellent and underrated charcuterie tray. Those interested in touring the brewing operation must visit on a Saturday afternoon.

Green Bay would be an excellent stop on the way to Door County; after all, the city is just a 45-minute drive from the heart of the peninsula.

Aerial view of the Wisconsin Dells.

9. Wisconsin Dells, Wisconsin

Another fun day-trip opportunity from Milwaukee is the Wisconsin Dells area. Known as the water-park capital of the world, the Dells are located in southern Wisconsin less than 2 hours from Milwaukee by car. One great spot to visit is Noah’s Ark Water Park, the largest in the country, which features more than 50 waterslides. A family-friendly eatery there is Moosejaw Pizza, which also houses the Dells Brewing Company. The staff provides free antler headbands to all visitors for lots of family fun. Those interested in outdoor activities should consider the ropes course, zip-lining, horseback riding, or the signature Duck boat tours.

The Dells area would be a great stop on the way to Madison.

As you can see, there are countless wonderful day-trip opportunities from the Milwaukee area. These are just a few of the many excursions available.