For the 50+ Traveler

Some activities during our visits to Kenosha and Milwaukee were hosted by the Kenosha Area Convention & Visitors Bureau and Visit Milwaukee, respectively. All opinions expressed are our own and are based on our experiences.

Wisconsin is one of the greatest driving destinations in the Midwest. You can start anywhere and find many places to stop along the way. Some spots are great for a day of play, and others could keep you busy for a weekend or more. Different drives offer scenic pleasures and activities that vary by season.

One of our favorite drives in the summer months is along the beautiful shoreline of Lake Michigan. We’ll start right across the Illinois border in Kenosha, Wisconsin, and end at Sister Bay in gorgeous Door County. Come along with us on this fun road trip up the eastern side of Wisconsin.

The town of Kenosha, Wisconsin.
Sue Reddel and Diana Laskaris


Our first stop is the bustling city of Kenosha. You can grab a European-style picnic lunch from The Buzz and take it to one of the many Kenosha parks, where you can take in a free concert or sit and watch the goings-on. Then visit the Civil War Museum, which presents the Civil War from the perspective of the Midwestern states.

Hop onto a beautifully restored electric street car for a loop around the city. Art lovers will enjoy the galleries, the Anderson Arts Center, and the fabulous Sculpture Walk along Kenosha’s HarborPark. If you’re there on a Saturday, check out the large Kenosha HarborMarket. Anglers can rent a fishing charter and take their catch to the Boat House, where the staff will cook it up for you.

Visit the world-famous Mars Cheese Castle for samples galore and cheesy souvenirs. The Southport Light Station Museum and North Pier Lighthouse are also fun to explore.

If you want to spend the night, try The Stella Hotel & Ballroom. There’s a great restaurant, whiskey bar, and even a rooftop bar for enjoying the stars.

Wind Point Lighthouse in Racine, Wisconsin.


For a special evening out, dine at the Hobnob for a classic Wisconsin supper club experience on the Kenosha-Racine border. Be sure to make a reservation in advance and have an Old-Fashioned on the lakeside patio. Don’t forget the signature ice cream drink for dessert!

The Racine Heritage Museum has collections focused on Racine factories such as Johnson Wax as well as exhibits highlighting the Underground Railway, the abolitionist movement, and Frank Lloyd Wright. Speaking of Frank Lloyd Wright, you can visit Wingspread, Wright’s largest Prairie-style home, as well as the SC Johnson Administration Building, which was also designed by the architect.

Check out the many restaurants in downtown Racine and enjoy the galleries, shops, and historic buildings. When your sweet tooth calls, visit the O&H Danish Bakery for an authentic taste of their famous pastry, the Racine Kringle.

Downtown Milwaukee, Wisconsin.


Milwaukee is hard to do in a day, so stay longer if you can. Here are a few highlights you won’t want to miss.

The Milwaukee Art Museum has great art and lakeside views. You can also see the intriguing Reiman Bridge connecting the museum to the business district. Even if you’re not into motorcycles, you'll probably find the Harley-Davidson Museum as fascinating as we did. The history of the famous company and its bikes really come to life.

Beer lovers will want to see the Pabst Mansion or go for a tour and tasting at Lakefront Brewery. Look for the picture of Laverne & Shirley on the wall. Stroll down Brady Street or through the Milwaukee Public Market in the Historic Third Ward for dining, shopping, and entertainment. Plan in advance if you want to take in the performances at Summerfest, one of the world’s premier music festivals. And, just for kicks, stand in front of the Bronz Fonz statue and say “Ayyyy!” before you leave town.

This is just a fraction of what Milwaukee has to offer. If you can, stay someplace fun like the Brewhouse Inn & Suites, with the old copper brewing kettles still in the lobby.

The town of Port Washington, Wisconsin.

Port Washington

You’ll feel like you're in a seaside village outside Wisconsin when you visit the cute little maritime town of Port Washington.

Check out Main Street for shops, restaurants, and events. For a touch of nature, enjoy the many parks and nature preserves. One of our favorite combinations is wine and chocolate, so if that sounds good to you, too, visit the Vines to Cellar Winery and The Chocolate Chisel sweet shop for some treats.

There are plenty of golfing as well as boating and fishing opportunities here. Port Washington also has a lovely farmers market on Saturdays. If you’re around for the Fourth of July celebration, you’ll find a parade, picnic, live music, and fireworks lighting the night.

Aerial view of Sheboygan, Wisconsin.


Home of the famous Sheboygan bratwurst, this fun city has a lot more going for it. The Bookworm Gardens offer a charming botanical way to experience your favorite children’s tales. You can see the Lottie Cooper shipwreck, with its own interesting tale.

Sheboygan is also known for great events. The car races at Road America are popular, and Brat Days is a favorite celebration of the famous sausage. You can enjoy great eats on a Food Truck Monday, or grab a bite on a Thursday evening and take in a free concert at the John Michael Kohler Arts Center.

Taste some local craft beer at 3 Sheeps Brewing Co. or enjoy water activities like swimming, surfing, sailing, or paddling.

Check out these other great ways to play in this fun and beautiful lakeside community.

Fox River in Green Bay, Wisconsin.

Green Bay

Like Milwaukee, Green Bay is a lot to manage in just a day, especially for sports fans. If you can, spend some time exploring the city. Take a tour of Lambeau Field and see the highlights and history at the Green Bay Packers Hall of Fame. Then pick up an authentic cheesehead hat at the Packers Pro Shop.

If you’re not a fan, don’t worry. Head outdoors at the 700-acre Bay Beach Wildlife Sanctuary and the Green Bay Botanical Garden. Enjoy some fresh air and the beauty of nature. The free Waterboard Warriors Water Ski Show Team is fun to watch throughout the summer.

If you want to get active, head over to the Bay Beach Amusement Park, which is full of rides, games, and tons of fun stuff to do.

The National Railroad Museum tells the story of the locomotive and has a large collection of trains, artifacts, and photo archives.

When you want to wind down, head over to Captain’s Walk Winery or Badger State Brewing for a drink and fun surroundings. For fine dining, visit Three Three Five or Republic Chophouse, or take your pick of casual or fine dining at the eclectic Chefusion.

The Ridges Sanctuary near Baileys Harbor, Wisconsin.

Baileys Harbor

Now you’ll head into gorgeous Door County, one of the most picturesque parts of the country. You will have many options for places to stop. We’ve chosen just a couple, but feel free to visit any of the towns along the way. Each has its own unique charm and beauty.

Baileys Harbor lets you walk on the wild side with its more than 6,000 acres of public lands, beaches, and parks. The Ridges Sanctuary has miles of trails that are great for exploring. Toft Point State Natural Area offers great hiking, bird-watching and wildlife viewing, and virgin forests.

If you’re a water lover, you won’t want to miss Kangaroo Lake, the largest inland lake in Door County, where you can swim, paddle, or head over to the Kangaroo Lake Nature Preserve to explore the trails and watch for white egrets, great blue herons, bald eagles, and other feathered friends.

To satisfy your hunger for great dining and a beautiful view, check out Florian II Lakeshore Supper Club. They’re known for their barbecue ribs, early-bird specials, and live music on the weekends.

Baileys Harbor hosts the Door County Beer Festival and the fun Food Trucks & Floaties event, where you can really do whatever floats your boat -- or yourself.

The town of Sister Bay, Wisconsin.

Sister Bay

Although we could go on and on, we’ll end our Wisconsin road trip with the lovely and quirky Sister Bay.

We say lovely because it offers a lovely marina and extensive waterfront park. With its pristine beaches, grassy parks, and tons of shoreline, Sister Bay is a place where you can do everything or nothing and have a wonderful time.

We say quirky because where else can you go to a restaurant that has goats dining on its rooftop? Yes, Al Johnson’s Swedish Restaurant and Butik has a roof covered in sod and goats grazing on it. It’s also got a fun and cozy log-cabin feel. They serve traditional Swedish specialties, including Swedish pancakes, which you can learn to make. Don’t believe us? Check out the Goat Cam to see what’s happening now.

You can also take a scenic boat tour or visit the Door County Creamery for artisanal goat's milk, cheese, and gelato made at the nearby farm. You can even take a lunchtime tour of the farm.

After checking out the local arts at places like the Frykman Studio Gallery, you’ll want to relax. There’s nothing more civilized in our book than tea, so get yourself some tea to go from Tea Thyme in Door County for your journey back home.

We hope this tempts you to make a wonderful Wisconsin road trip.