Walking from Milwaukee to Chicago

by John Greenfield

[This piece also runs in this week's New City magazine, www.newcitychicago.com.]

It’s a Thursday evening in late June and I’m clutching a pint in the Exchequer Pub on Wabash, not drunk but completely trashed after walking a hundred miles. Kirsten Grove, the Chicago Department of Transportation’s pedestrian program coordinator, and other CDOT staff who’ve met us there raise a toast to my trek. I smile weakly and thank them but I’m distracted by my aching back, sore legs and especially my throbbing feet.

I’ve bicycled from Chicago to Milwaukee a dozen or so times, including several trips during the dead of winter on the annual Frozen Snot Century ride. But lately I’ve been getting interested in walking as a form of travel that helps me take in more of my surroundings by slowing me down.

This year I’ve made a project of hiking the length of some of our city’s key thoroughfares, like Halsted, Grand and Archer. On each trip I met cool people, ate good food, saw fascinating scenery and drank in dive bars I’d never have noticed pedaling by three times as fast.

After I checked out the book Biking on Bike Trails between Chicago & Milwaukee by Peter Blommer, it occurred to me that walking between the two cities would make for a memorable journey. Blommer details a route that takes advantage of the many multi-use paths along the way - 80% of the itinerary is car-free.

I decided to hike from the Milwaukee Art Museum to the Art Institute of Chicago over four days. To cover 25 miles a day I’d have to travel fast and light so rather than take a tent and sleeping bag I opted to “credit card camp,” staying at fleabag motels. I packed a messenger bag with the bare necessities and caught the Amtrak Hiawatha north on a Monday morning.

The Milwaukee pedestrian coordinator, Dave Schlabowske, whose brother I know from the Chicago music scene, had agreed to walk me part of the way out of town. He meets me at the station and we hoof it to Lake Michigan and the Calatrava-designed art museum with its skeletal, retractable wings. I officially start my journey at 10:40 am.

Schlabowske suggests we backtrack to the Milwaukee River and stroll south along the city’s new riverwalk lined with cafes and brewpubs. The promenade was the brainchild of ex-Mayor John Norquist who resigned during a sex scandal and now heads the Congress for the New Urbanism, based in Chicago.

After Schlabowske says farewell at the confluence of the Milwaukee, Menomonee and Kinnickinnic rivers, I follow signs for Route 32, the secondary highway that leads to Illinois, hugging the lakeshore. Soon I spy the Allen-Bradley Clock Tower, the world’s largest four-faced clock with octagonal faces nearly twice as large as Big Ben’s.


At 1st and Kinnickinic St. a mural depicts civil rights figures from around the world, from Nelson Mandela to Hmong leader Vang Pao; from Cuban political theorist Pedro Campos to Milwaukee fair-housing activist Father James Groppi. Crossing the Kinnickkinnic River I’m in the Bayview neighborhood with its many quirky independent businesses.

Grabbing a salami sandwich at an Italian grocery owned by Father Groppi’s family, I head east to Cupertino Park for a view of a marina and the city’s modest skyline. From there, as recommended by Blommer, I pick up the Oak Leaf Bike Trail heading southeast out of town past pebbly beaches full of Canada geese and into lush woods.

Emerging in a park in the suburb of Cudahy I see a multiracial group of teens playing soccer. One of the boys calls, “Look behind you.” “What’s that?” I ask. “That girl – she’s 17,” he said pointing to one of his friends. “She likes you.” I chuckle nervously and keep walking. A beefy guy with a mustache walks past them northbound and the kid tries the same gag. “Don’t cause me any problems,” warns the man.

I get back on 32 and it becomes a highway with no sidewalks as I enter the village of Oak Creek. Walking on the left shoulder facing rush hour traffic, I flag down a couple of fresh-faced bicyclists with saddlebags. Joe Bell and Colin Bortner are riding cross-country, as I’d done the previous summer. They’d started in Rochester, NY, and are heading to Seattle after visiting friends in Chicago’s western suburbs.


Well-scrubbed cyclists usually get a warm reception from curious locals, but as I continue down the busy road I realize that in our car-centric culture people who travel by foot are often viewed with suspicion. In fact most people I see walking down this highway seem to be troubled teens or down-on-their-luck adults. As the northbound commuters rush by me, my possessions on my back, I feel temporarily alienated from mainstream society, little more than a hobo.

South of Milwaukee County, the east-west roads are named, Detroit-style, according to their distance from downtown Racine. Sweaty and exhausted I take a break at the Brass Rail tavern at 6 Mile Rd. This dive has a half-assed pirate theme: Jolly Roger flags, a model ship behind the bar and numerous plastic skeletons. When I’ve nearly drained my $1 draft, the bartender, his hand in a splint, says, “Let me see that glass – there’s something wrong with it,” and refills it for free.

After a big plate of pasta at a red sauce Italian joint across the street, I walk another mile or so on 32 to the Country Inn Motel, arriving at 9:10 pm. Like most budget hotels I’ve stayed at in rural America, it’s owned by Indian-Americans, probably immigrants from the western state of Gujurat. I sleep like a baby in the cool, clean room.

The next morning I grab coffee at Mocha Lisa at 4 ½ Mile Rd. In a secluded nook of the café with a couch, a sign reads “Four drink minimum for making out in this room. This room is not available by the hour.” From there I get on the North Racine Bike Path, a rails-to-trails that goes past wetlands with blue spruce and Queen Anne’s lace with a soundtrack of chirping birds. I find myself daydreaming about various plans and schemes as I stroll.


After the path ends I get back on 32, now called Douglas Ave. and walk towards downtown Racine as cottonwood seeds blow across the gritty street. The city claims to have the largest population of Danes in the U.S., so I stop at the O & H Danish Bakery, 1841 Douglas, to sample a rich slice of kringle, the ring-shaped pastry that is the local specialty.

Racine’s boutique-lined Main Street is decorated with 3’ tall spheres, customized by artists Cows-On-Parade style. “Toulouse-Laugoose Egg” by Robert W. Anderson featured a top-hatted fowl perched on an homage to “At the Moulin Rouge” while Jeff Lavonian’s planet Earth covered with small colored glass balls is titled “The World is Losing its Marbles.”

I trek west to the towering, Wright-designed Johnson Wax building and continue through the south side on Racine St., passing the local NAACP branch. A few blocks later I notice smoke coming from the next block - the side porch of an old house is on fire. As I rubberneck from the alley with a group of locals, firefighters swiftly appear and douse the blaze.


After following 32 for a couple miles, I pick up the Racine County / Kenosha County Bike Path, another converted rail bed. Boredom sets in so I start listening to the Chicago band the Sea and Cake on my iPod. Leaving the trail on the north side of Kenosha, Wisconsin’s fourth largest city, my left shoulder is killing me from carrying my one-strap bag. There’s a message on my cell from Jim, who works with me at a bike shop. “Oh, my feet hurt,” he says. “Keep walking homie.”

I head east and walk downtown on a lakefront bike path lake, soothed by view of the cobalt water and air scented with honeysuckle. Catching sight of the red Pierhead Lighthouse I feel the beginnings of blisters on my toes and stop to adjust my socks.

Crossing a bridge over a marina into town I stop at Paddy O’s Pub, 5022 5th Ave., for a cold one. “Zippy” the bartender, wears a bushy beard, a straw cowboy hat and a “Nuke the Whales” t-shirt. He’s telling the regulars about going to Pazzo’s, a fancy local Italian restaurant, with a buddy one afternoon and spending $200 on wine and snails.


“We were drunk and I was dressed like this, so when the suits started showing up for dinner they asked us to leave,” he complains. “Sounds like a civil rights lawsuit to me,” says a barfly with a few teeth missing. “It was no problem,” says Zippy. “I just went in their bathroom and pissed all over their toilet paper.”

At sunset I sneak into the Keno Drive-In Theater on the south side of town. I figure it’s OK since I don’t have a car and I’m buying a brat at the snack bar. “Kung Fu Panda” is playing so I sit on my raincoat on the grassy area in front of the screen within earshot of car radios tuned to the soundtrack. As a scruffy, single man watching a children’s movie I seem to be mistaken for a sexual predator - one of the families next to me drives off and parks in a different spot.

I’d called RV Sports Motel in Pleasant Prairie that afternoon, and the owner, also Indian-American, assured me I’d have no problem getting in. But when I show up after the movie he says the place is full. I protest and he offers me a shabby room with no hot water at full price, but promises I can bathe in another unit in the morning. Grimy, I take a painfully cold shower anyway and go to bed slightly resentful and a little lonely.

Crossing the “Cheddar Curtain” on Day 3, I’m struck by how the scenery immediately changes from pretty, rolling terrain to grim flatlands when you enter Illinois. The main drag of Winthrop Harbor, IL, the state’s northeastern-most town and home of the largest marina on the Great Lakes, is lined with gas stations, liquor stores and bait shops.


I breakfast in Zion, founded in 1901 by Scotsman John Alexander Dowie as a home for his sect the Christian Catholic Church. North-south streets named after biblical people and places are reminders of the city’s roots as a theocracy. At the Star Lite Restaurant, I enjoy a chili omelet but I’m curious about the Ballpark Skillet: eggs, potatoes, green peppers, onions, American cheese and sliced hotdogs.

On the west side of town I pick up the Robert McClory Bike Trail but in Waukegan, the blue-collar city that produced Ray Bradbury and Jack Benny, I grow tired of the monotonous, dead-straight trail and detour into neighborhood streets. A Rottweiler chained on a front lawn barks and lunges at me. I’m in a foul mood from my aching feet, so when the owner comes out I yell at her. “You should keep your dog on a shorter leash. No one can use the sidewalk.” “Do you live in this neighborhood?” she demands. “No, but I’m allowed to walk here,” I fire back.

Returning to the path I walk through a glass-strewn industrial area near Great Lakes Naval Training Center in North Chicago and pass a Metra station, tempted to hop a train home. Entering Lake Bluff I abruptly find myself in the posh northern suburbs that are the backdrop for John Hughes’ teen comedies.

I rest on a bench in the village square and take stock of my throbbing extremities. The blisters are getting bigger and hurt so much I’m wondering if I’ll be able to keep walking. But soon after gulping painkillers outside a Lake Forest Walgreens my feet become miraculously numb.

I detour into the Fort Sheridan development, formerly a military installation that housed the troops who stormed Chicago to shut down the Pullman Strike in 1894, leading to the deaths of 13 workers. There I admire a lifelike statue of a soldier on horseback, wearing a Civil War-style cap and holding a banner, galloping off into the now setting sun.


Trudging south down Sheridan Road I’ve got my fingers crossed that the Hotel Moraine actually exists. When I’d searched the Internet for cheap lodging in the ritzy North Shore, the hotel at 700 N. Sheridan in Highwood seemed to be my only option, but every time I called I got voicemail.

Suddenly it’s looming in front of me, a five-story brick box with lettering in big, gold cursive, and my heart leaps. But as I get nearer I see there’s only a car or two in the parking lot. The lobby’s dark; power tools and an Orange Crush box lie on the floor.

My hopes of sleeping indoors dashed, I accept that I’m going to have to crash in the woods somewhere. I buy a baby blanket in a dollar store and brood about my fate over a cheeseburger on pumpernickle at the Nite ‘N’ Gale, an old-school cocktail lounge with red leather booths and LeRoy Neiman prints.

As I approach Ravinia Park along the Green Bay Trail in the dark, the path is packed with fans leaving a Robert Plant and Alison Krause concert. I’m wearing my headlamp and one woman looks startled I pass her. “David, are you there?” she cries. “What’s the matter,” says David. “Are you afraid of the miner guy?”

Heading a bit west along the Lake-Cook county line I find a little mowed patch in a forest preserve just off of Green Bay Rd., next to the Chicago Botanic Gardens. It’s hidden from the police by surrounding tall grass but close enough to the highway for protection from serial killers.

The night is chilly and misty, so I put on all the clothes I have with me, cinch the hood of my raincoat around my head, place a plastic bag under my behind and wrap the tiny baby blanket around my bare legs. I feel new sympathy for homeless people. I’m just barely warm enough and mosquitoes harass me all night, but earplugs and eyeshades block the sound and lights of traffic and I manage to get a few hours sleep.

In the morning the Green Bay Trail takes me through Glencoe and Winnetka to Kenilworth where I cut east to Sheridan Rd. and a view of the lake. Nearing the Baha’i Temple, that giant orange juicer made of lacey, white concrete, the road is torn up for many blocks for sewer renovations and for once I’m glad to be on foot instead of two wheels.

The Evanston Arts Center, next door to a lighthouse, features an installation of giant bottle shapes sunk into the front lawn, assembled from actual glass bottles decorated with black magic marker. I detour onto a peninsula next to the Northwestern campus and catch an inspiring view of the Loop.


Heading back west to Clark St. with my feet feeling like lumps of clay I soon pass the Calvary Catholic Cemetery and cross Howard St. into Chicago’s Rogers Park neighborhood. I’m glad to be back in my city, but a little disappointed by a depressing view of strip malls and big box stores of the new Gateway Center. Fortunately, this “Geography of Nowhere” landscape quickly yields to miles of diverse small businesses.

On my way downtown on Clark I see restaurants offering almost every known ethnic cuisine and I immediately stop at Cuetzala restaurant, 7350 N. The al pastor (Mexican gyros), tilapia and cabeza (cow head) tacos are tasty, but due to the recent salmonella scare there are no tomatoes in the fresh salsa, just chopped onions, garlic, cilantro and chiles.


Soon I’m in Andersonville with its colorful shops, sidewalk cafes and a couple of my favorite taverns, Simon’s and the Hopleaf. Passing Graceland Cemetery and Wrigley Field, I head a bit east to the Addison Red Line station and pick up Kirsten Grove, who’d agreed to escort me downtown so my pilgrimage would be bookended by the ped coordinators from both towns. Since CDOT employees are not supposed talk to the media without prior approval, I promise her that any discussions we have along the way about narrow sidewalks or dangerous intersections will be off-the-record.

In Old Town we head south on Wells St. to chat with a couple of other CDOT staffers who are conducting bicycle traffic counts, then walk east on Erie to Michigan. It’s exhilarating to complete my journey by joining the rush hour throngs on the Magnificent Mile, one of America’s busiest thoroughfares.


We snap a few pictures by one of the Art Institute’s bronze lions then adjourn to the old-school Exchequer, a few blocks away. After I regale the group with road stories I feel nearly comatose from physical exhaustion plus the twin soporifics of beer and deep-dish pizza, so I spring for a cab home.

As I’m standing in the shower with the warm water soothing my shoulders, it occurs to me that I’ve finished the longest walk of my life. And I feel like I know the territory between Milwaukee and Chicago intimately now – I’ve stitched together the two towns.

Sitting on my bed I stare at my feet once more. Yellow, fluid-filled pillows have blossomed on both of my pinky toes, between my right big toe and its neighbor, and on the ball of my right foot. Despite the pain, at this moment I’m happy and satisfied: proud of my accomplishment and thrilled to be spending the night indoors.