On the Road in Wisconsin: Summer Stops in Madison, Milwaukee & Sheboygan

2025 was a time of Wisconsin adventure for our family. While we've made a few dedicated one night visits to Milwaukee over the years, this years visit was our first focused on seeing a concert (Lumineers) at a terrific venue (American Family Insurance Amphitheater) while appreciating as much as we could of what makes Milwaukee great. We doubled down on the out of town concert thing with a trip to Madison to see Coldplay at Camp Randall Stadium and enjoyed the outdoor experience around Madisons terrific lakes and its shining state capital.

The summer Wisconsin adventures continued an hour past Milwaukee on the coast of Lake Michigan where we experienced stunning beaches and cool Sheboygan.

Take a peek below for some favorites and a few recommendations.

Milwaukee

While our Milwaukee visit was centered around seeing the Lumineers in concert, we made sure to turn our visit into an overnight stay and a full day in Milwaukee visiting some of our favorite spots and finding some new ones.

Gloriosos

• This traditional Italian deli is half grocery store (filled with wine and mostly imported sauces, condiments, dry pasta, and boasting an impressive frozen section) with the other half featuring a large deli spinning up Italian deli sandwiches, paninis and salads. Gloriosos also has a small butcher area and an Italian desert bar where they serve gelato and make homemade Italian cookies and cannoli. I always stop here when I come through Milwaukee for lunch, some shopping or to grab some prosciutto and cheese (from their impressive cheese aisles) for home.

Brady Street

• Gloriosos is on Brady Street as are many cool bars (Garage on Brady, Nomad World Pub), shops, bakeries and coffee shops, including the crunchy Rochambo Coffee and Tea house, which is a great hang and embodies this unique part of Milwaukee. We actually stopped at Rochambo (and of course Gloriosos) on the way to Sheboygan as part of another summer Wisconsin adventure which I highlight below.

3rd ward

• Popular and fun area with many good dining and drinking options within walking distance of one other. We made our way through this area as we walked to the concert venue, stopping for a beer along the way at laid back Wizard Works Brewing Company. Other recommended places in the area include The Wicked Hop, Uncle Wolfies (terrific brunch spot located in a residential building) and Cafe Benenlux, which is uniquely focused on food and drink from Belgium, The Netherlands and Luxembourg.

Milwaukee Public Market

• Also located in the Third Ward, this is a great place to get a drink and sit outside on a nice day (or upstairs on a not so nice one) and to dine at one of the many restaurants in the market. There are great shopping options in the market also including St. Paul Fish Company, West Allis Cheese & Sausage Shop, The Spice House and Freese's Candy Shoppe.

Lakefront

• Milwaukee is blessed to have direct access to Lake Michigan, just like Chicago. My favorite way to get to the lake in Milwaukee is to stroll up Brady Street and head down the stairs that connect to the path that provides access to Veterans Park and the Lakefront. Colectivo Coffee Shop has a great location in the area if you need a pick me up between your walk, run or bike ride.

Veterans Park

• This is a great place to appreciate the Lakefront over a walk or jog and is the best place in Milwaukee that I've found to enoy sprawling outdoor space near the lake.

Milwaukee Art Museum

• They have a solid collection in a great location near the lake with the Quadracci Pavilion being a particularly famous and iconic structure.

Music at Amphitheater and Summerfest

• The best outdoor Amphitheater lawn concert experiences I've had in my life have been at the American Family Insurance Amphitheater. They have great sound, terrific sightlines and its easy to get around. Your also located right on the lake with an incredible bridge view.

• Summerfest is a great Midwest music festival which takes place in an area dedicated to having festivals. This makes it easy to find anything you need, whether it be a drink, snack or a washroom. The Amphitheater is located within the Summerfest festival grounds.

Lakefront brewery

• Great brewery in a unique location that straddles the river. They have a good tour and solid beer and food.

Riverwalk

• Its a must to take in the river experience in Milwaukee as you walk through the downtown. Its's like a much smaller version of the Chicago riverwalk and is a great way to aquaint yourself with downtown Milwaukee.

Oktoberfest and Bavarian Bierhaus

• This isn't exactly in Milwaukee - it's located in nearby Glendale - but it's certainly worth mentioning. The Bavarian Brauhaus is as authentically German as it gets with a dedicated festival grounds area to host its annual Oktoberfest celebrations which take place over 5 successive weekends from early September to early October. The celebrations are alot of fun for everyone with German beer, music and dancing and plates of roasted pig and chicken served up from the dedicated roasting pit areas located onsite.

Sheboygan

A visit to Sheboygan had been on my my list for sometime (about 5 years), but it seemed like we always ended up in Michigan or Indiana when we wanted to spend a day or two in a town near Lake Michigan. I'm glad we finally followed through and turned the car towards Wisconsin this summer.

Sheboygan is a cool town of 50,000 on the shores of some of the best Lake Michigan beaches I've experienced in any of my travels throughout Indiana, Illinois and Michigan over the years. Sheboygan has alot to offer and its pretty well versed.

The town is known worldwide for its many terrific golf courses and is home to truly one of the best courses in the world in Whistling Straits (it has hosted 4 majors and a Ryder Cup), but golfing is only one of Sheboygans chapters and I didn't come for the golf.

Sheboygan isn't a quaint town, whose population swells in the summer due to tourism so significantly that the character of the town is drastically impacted. There are plenty of tourists in Sheboygan, but this is not the Indiana Dunes, New Buffalo or one of the towns in Door County a few hours drive further up the road. Sheboygan is a decent size town with a great restaurant scene, one of the best Midwest breweries I've visited, amazing beaches, boating opportunities and plenty of options to bike and walk outdoors. Here are the highlights from our midsummer trip to Sheboygan, one we hope to repeat in the near future.

• Kohler-Andrae state park has places to hike and walk, but the main highlight is the amazing stretch of Lake Michigan beach, some of the best on any side of Lake Michigan, where you can relax, swim, surf and bodysurf while enjoying the surrounding beauty. They have some good wooden plank trails that vary from .25 miles to 2.5 miles in length with the 2 mile Dunes Cordwalk and 1 mile Woodlands Dunes Trail offering the best views. The trails you walk meander up and down through the rolling dunes with dune grass all around and the beautiful beach and Lake Michigan next to you.

  

• Deland beach and the waterfront are great spots near downtown Sheboygan to enoy the lake and walk along the beach. They have a bathroom and small café and there is a nice walk out on the land bridge to the lighthouse which reminds me of the pier in St. Joseph, Michigan.

  

• Food and Drink

  • Arrostos sandwiches is a banger of a spot where a NY transplant is doing some beautiful things between their daily homemade focaccia.

  • 3 Sheeps Brewing has great beer and an impressive onsite experience with LOTS of space. From live music to food trucks to festivals to bocce ball and gatherings of family and friends, this spot has it all. Bring your own food or grab something off a food truck, but settle in for some good beer, entertainment and relaxation. 3 Sheeps belongs in the same category as Surly in Minneapolis and Sierra Nevada in Asheville, two breweries with amazing indoor/outoor areas.

  • Harry's Diner is one of the best

    diners the United States has to offer. I mean, how can it be better? It looks like it was built in a factory with the old school booths, shiny everything and the decor and artwork which look like they were in some film or show that features diners (Diner, Pulp Fiction, Happy Days). Having a breakfast at Harry's is a must if your visiting Sheboygan. There are few places that I've been to in this country that offer a better overall diner experience (and I've spent alot of time in New Jersey, the U.S. diner capital).

  • You have to appreciate the South Pier part of Sheboygan near Blue Harbor resort for at least a bit. This is a terrific part of Sheboygan where the boats dock and make their way up and back through this water byway which connects the Sheboygan river to Lake Michigan. We enjoyed a bowlful of steamed mussels and a drink on the patio at Driftwood.

  • Paradigm coffee has great coffee, loose leaf tea and solid food in a cool setting in downtown Sheboygan with a wide open indoor area that gives way to a sprawling outdoor patio. We enjoyed this fantastically hip spot on both of the days we spent in Sheboygan.

  • The Saturday farmers market is quite the event with many food trucks and vendors serving a wide variety of options and offering an extremely impressive and diverse variety of produce.

Old Plank Trail bike ride

• This is a pleasant ride through the cornfields that crosses many country roads through Sheboygan and into Sheboygan Falls. There are plenty of spots to find some shade or take a break along the way, but its mostly a "get out and ride" trail with little to stop you from just riding through the countryside. You can ride as long as you want, but we did a total of 16 miles, picking up the Erie trailhead close to Sheboygan.

  
  

Madison

Our trip to Madison was also centered around a concert as we made our way to see Coldplay at Camp Randall stadium. This provided an opportunity to explore the Madison area once again and discover some new spots.

• Entering Camp Randall Stadium through the main entrance under the gates is a gorgeous walk and an impressive entrance to the 80,000 capacity stadium where the Big 10 University Wisconsin Badgers play their football games. Located in a neighborhood, this is a great place to see a game or concert that feels kind of like the neighborhood environment around Wrigley Field (home of the Chicago Cubs) in Chicago.

• Memorial Union beer garden is a great spot on the lake to relax, have a beer, watch the boaters and just appreciate how special this place is. It's really hard to believe this is part of the campus and I would really like to know if there are better campus spots in the country to have a drink and appreciate the beauty around them (as I would like to visit them).

• Walking around the Capitol building. All state capitals, particularly the ones in Austin and Madison, are impressive. They really stand out for the architecture and the majesty and grandness of it all. The Madison, Wisconsin version is probably my favorite that I've visited. Using the .6 mile walk to traverse the capital building is undoubtedly the best way to acquaint yourself with Madison. It offers numerous spots from which to appreciate the capital building and its marble stairs, with shady trees and life all around. This is right at the heart of Madison. Some of Madisons best restaurants and locales are located on all sides across the circular street from the capital building. Most of the streets are pedestrian friendly and are popular with students, locals and tourists.

• Some of the spots I've most enjoyed around the Capitol include The Old Fashioned (they only serve Wisconsin centric food items and beer from Wisconsin breweries), The Coopers Tavern, Colectivo Coffee on the Square and Casetta Kitchen and Counter, which has some of the very best sandwiches I've tasted anywhere.

• Enjoy the lakes around Madison (it's part of what makes the city unique) and rent canoes at Brittingham Boats on the coast of Monona Bay. This is a great way to explore one of Madisons 5 lakes (Lake Monona) and offers terrific views of the state capital building from the water.

Check out this link for my take on another great Wisconsin spot @ Devils Lake State Park.