Weekend Road Trips: Circling Lake Michigan

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In my lifetime I have driven more than one million miles around the lower 48 United States. Weekend Road Trips is my way of sharing those experiences in a way that I hope helps others enjoy and appreciate the American road trip as much as I do.

For the sake of the majority, each trip will begin in a major city and presume your available weekend starts on Friday afternoon and ends on Sunday night weekend, but can be adapted to any location and schedule with a little creativity and maybe some nighttime driving.

Most importantly, and in a break from the way most of us are used to traveling, we will be avoiding interstate highways unless absolutely necessary – and even then just momentarily.

While the US interstate system is a marvel of engineering and a great way to speed from city to city, keeping to US, state, county, and local roads shows us quaint, quiet towns frozen in decades past, and far fewer chain anythings.

For our second installment, we will discover some hidden gems around Lake Michigan. We’ll start in Chicago, but this trip can easily be adapted to any city along or near the loop, as far east as Cleveland (or even Pittsburgh with a little hustle or an extra day).

Friday afternoon: Chicago, Wisconsin Coast, Milwaukee

In keeping with the mantra that slower is better, we will start this trip crawling along Lake Michigan along North Lake Shore Drive. If your pooch likes the water and needs to run for a bit, stop off at the Montrose Dog Beach then head north on Sheridan Road towards Evanston.

Woman with dog

CHICAGO – SEPTEMBER 4: A dog and its owner play on Montrose Beach along Lake Michigan September 4, 2002 in Chicago. A new Chicago Park District ordinance allows owners to let their dogs run inside a fenced-in area of the beach unleashed. The two-month program started September 3 at Montrose Beach, the city’s first and only public beach to allow the dogs to romp. (Photo by Tim Boyle/Getty Images)

If you find yourself getting hungry as you leave Chicago in your mirrors, stop off at The Mean Weiner in Highwood for some fine roadside fare. And should your cholesterol need elevating, definitely sample the Borracho taco: al pastor, asada, chorizo, and tocino (that’s pork, steak, sausage, and bacon to you gringos).

With your bellies satisfied and your door handles greasy, head north on IL-137, which becomes WI-32 just as the scenery goes from grey to green.

Hopefully you will have some daylight left to enjoy the occasional lake views as you pass through Waukegan and Racine, but the real beauty lies at points further along so now is the time to make hay while the sun goes down and get yourself to Milwaukee.

While in Wisconsin you will definitely want to do as the Wisconsinites do and avail yourself of the myriad of local beer and cheese options. It may be late when you arrive, however, so head to MobCraft Brewery and Taproom, which keeps their kitchen open until midnight on weekends.

Or if you want something quick and easy, the Zócalo Food Park provides some stellar international offerings, live music, and even a sauna.

Milwaukee offers the typical array of lodging options, from the legendary Pfister Hotel downtown to more affordable spots north of the city or near the universities.

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