Quickie Summary: State “Trunk” Highway 20 connects Racine residents with points west, including Waterford, East Troy (and the nearby Alpine Valley), and Whitewater, accessed via U.S. 12 past Highway 20’s terminus. You catch some small-town flavor, ride rolling hills near Kettle Moraine, catch a train ride and explore Racine, especially the impressively redeveloping downtown and lakefront.
Highway 20 Road Trip
The Drive (West To East): Highway 20 begins at Highway 67 where U.S. Highway 12 veers off and starts heading west towards Whitewater and Madison – or south towards Elkhorn and Lake Geneva depending on your perspective.) There’s little around the intersection, although cars staying on U.S. 12 tend to move quickly and others may not pay attention to the stop signs.
The first town, East Troy (pop. 3,564), is probably best-known for its proximity to Alpine Valley. But it’s a full-fledged, all-American town in itself. It’s also east of the Town of Troy, but you probably figured that out already.
Highway 20 slides through the northern area of East Troy, but it’s worth a jog south to the town square, which features a number of buildings dating back to the 1850s and 1860s. Craft stores, saloons, and other small shops surround the town square. The town square also features the Cobblestone Bar (pictured above, 2088 Church St., 262-642-3735), which houses a history that includes a stay by President Lincoln and the reported haunting by two former owners who disappeared and were never heard from again. Not to freak you out, we’re just the messengers.
The town square also hosts the East Troy Brewery, which opened in a former bank building in 2019. Amidst the teller’s window area (which is now the main bar) or within the original vault – which contains some really cool artifacts to check out – you can explore their signature craft beers or enjoy guest selections from other Wisconsin breweries. They’re also known for a good food menu. Right across National Avenue (County ES, once Historic Highway 15, the main road between Milwaukee and Beloit until I-43 opened in 1973), you’ll find one of the oldest continuously operating bars in Wisconsin: the East Troy House.
East Troy shows up on a lot of concert t-shirts because the Alpine Valley Music Theatre is located just south of town, off Highway 120 which technically starts in the town square but should start at Highway 20. Alpine Valley has hosted an incredible array of concerts with some huge names since its opening in 1977, when the huge names in question were Boz Scaggs, Neil Sedaka and Helen Reddy – they kicked off the first set of shows. Following since has been everyone from Frank Sinatra to Motley Crue, Aerosmith and Boston to the Grateful Dead. Jimmy Buffett and Dave Matthews perform here pretty much every summer, keeping the snack food industry humming. Plenty of videos have been shot here, including Motley Crue’s “Same Ol’ Situation”, the Grateful Dead’s “Touch of Grey”, the Black Crowes’ “Hard To Handle” and, more recently, Korn’s “Politics”. Coldplay had their largest American audience ever at Alpine Valley until they performed at the Super Bowl in 2016.
A popular attraction in East Troy is the East Troy Electric Railroad & Museum, housed in a station that served one of the last Interurban lines that once graced southeastern Wisconsin.
Through exhibits and pictures, the museum offers a glimpse of what train service was like when the line began in 1907 and was run by The Milwaukee Electric Railway & Light Company (TMER&L for short.) You can still ride a vestige of the railroad’s former glory on the East Troy Electric Railroad, which runs the old-fashioned cars on a 10-mile journey between East Troy and the Elegant Farmer just southwest of Mukwonago (yes, the place that bakes apple pies in a brown bag). Service runs from May through October and gives you a nice flavor of what the Interurbans were like back when the Milwaukee area was served with hundreds of miles of train lines that reached to East Troy, Watertown and Sheboygan. The museum is on Church Street between downtown East Troy and Highway 20; it’s off the beaten path, but well-marked for visitors to find.
East of East Troy, the junctions with County ES (the old Highway 15 from Beloit to Milwaukee) and I-43 provide access to stores and services, including a 24-hour McDonald’s. So if you’re driving through at 3am and need Chicken McNuggets, you’re set.
The drive between East Troy and Waterford features more rolling hills and forested areas. Racine County begins as you enter a shaded bend along a hillside that’s more characteristic of western Wisconsin than the southeast.
The rapidly-growing city of Waterford (pop. 4,048) is about four miles east of the Racine-Walworth County line, where Highway 83 hooks up with 20 for the ride into town. Originally known by its Potawatomi name of Tichigan, a name that lives on in the form of a nearby lake, Waterford is now named partially due to its narrow crossing point over the Fox River at Main Street (where one could easily, as they used to say, “ford the water”.) Downtown features stores and bars a’plenty and some nice parkland along the river. Waterford itself is celebrating its 100th anniversary. Highway 20 takes you through the heart of town and then to the southeast, where Highway 83 breaks off and veers south toward Illinois at the intersection with Highway 36; 20 continues east for the push into Racine.
Between Waterford and Racine the land flattens out a bit and farms get larger, until they get taken over by the development west of Racine in the towns of Yorkville, Ives Grove and Mount Pleasant. You cross Highway 75 and U.S. Highway 45 (which joins 20 for one mile). The rules out here in the countryside are different; school speed zones in the town of Yorkville are 45 mph. You can say all you want about the pace of country life being slower, but in the city, school zones are more like 15 or 20 mph. At Highway 75 and County S is Beaumont Park, named after the first batter in World Series history. Ginger Beaumont, born in Rochester, played for the Pittsburgh Pirates and batted against famed pitcher Cy Young in the 1903 World Series. He went 0-for-5 in that game, just in case you were wondering.
A defining point along Highway 20 is the junction with I-41/94 (Exit 333) in Mount Pleasant. You’re 34 miles east of the western terminus and about 10 miles from Lake Michigan, and from this point on east Highway 20 is a major, multi-lane thoroughfare all the way into Racine. While farmland still exists for a while past the array of hotels, gas stations, and restaurants at the interchange, this is changing quickly. Some of the intersections, including near Renaissance Boulevard and County H, lead you to entertainment and sports complexes, technical college campuses, and major offices for some of the biggest companies in the area including InSinkErator, Johnson Controls, Kerry Ingredients, Evinrude-BRP, and one of our favorite names, Putzmeister America, Inc. Part of the concentration here is because of access to not only Highway 20, but the main passenger and freight rail line between Milwaukee to the north and Chicago to the south.
This is all part of Sturtevant (pop. 5,451), by the way, a “gateway” that towers over tracks where the Amtrak Hiawatha makes its seven or eight daily runs between Milwaukee and Chicago, the city being one of the few stops along the way. It’s easily visible from Highway 20 and anchors this fast-growing area of development. With the FoxConn development just to the south, it will only get busier.
Eastward from Sturtevant, it’s pretty much city for the rest of the way. Highway 20 is Washington Avenue going into Racine; large stores, car dealerships and chain restaurants dot the landscape (as does Racine Case High School) as you approach the city. At the junction with Green Bay Ave. (Highway 31), you reach the city itself.
Racine (pop. 81,855) calls itself the Belle City and is Wisconsin’s fifth-largest. The French may have named the city (Racine is French for “root”, after the Root River which flows into Lake Michigan here), but Danish immigrants left the tastiest mark on the city; Racine is known as the “Kringle Capital of the World”. Famous locales like Lehmann’s, O&H, and the Larsen Bakery (which is located right along Highway 20 at 3311 Washington Avenue near the intersection with Hayes Street, in an area known as Kringleville or Little Denmark) crank out millions of the tasty iced and filled pastries every year and ship them worldwide. You, however, can stop in for a fresh one right there. They’re best that way.
Racine’s industrial and entrepreneurial history now spans three centuries. Home to major companies like J.I. Case (now Case IH, where the IH stands for “International Harvester”) and S.C. Johnson, it’s where the garbage disposal was invented in 1927; In-Sink-Erator still calls Racine home. It’s also where malted milk was invented in 1887 by William Horlick, who now has a high school named after him (they do not have a malted milk stand, however, according to my limited research.)
Many cities the size of Racine host minor-league baseball, but Racine hosts minor-league football. The Racine Raiders of the North American Football League are one of the most respected minor-league football organizations in the country and have been around for over 50 years. The Raiders have sent players to the NFL over the years, although unfortunately most of them went to the Vikings. They play at Horlick Field, on the north side of town, just a few miles off Highway 20’s path. Their season begins in June, so there’s no talk of frozen tundra here.
Highway 20 continues east as Washington Avenue, winding around parkland and through the Uptown neighborhood, formerly known as The Junction back when two railroads crossed here and Washington Avenue was a plank road charging tolls. Follow the signs past a split where it becomes 7th Street, and you will find yourself on a downtown strip, lined with stores. Highway 20 ends one-way eastbound as 7th Street (westbound runs on 6th Street) at the intersection with Main, at which point you’re also on Highway 32 and just blocks away from Lake Michigan.
Downtown Racine and the Harbor area offer a wealth of sights and things to do. The Racine Art Museum (441 S. Main St.) houses a series of contemporary craft exhibits and street-level displays while the Racine Heritage Museum (701 Main St.) houses a bird collection and other features from Racine’s early days. Monument Square (500 S. Main Street, just off Highway 20’s eastern end) offers a look back – and up – with its 61-foot high Civil War Soldiers Memorial, dedicated in 1884, when it was called Haymarket Square, while also giving a nod to the future with Wi-Fi Internet Access for anyone using their laptops in the square, perhaps imbibing in a beverage or meal from the surrounding stores. If you’re in the mood for an old-fashioned diner experience and one of the best-rated burgers in the state, by the way, a visit to the Kewpee (520 Wisconsin Ave.) should satisfy you, as it has for Racine residents since the 1920’s.
Racine’s attention to the lakefront is among the most impressive in the state. Buildings lining downtown streets offer increasingly busy storefronts, but their upper floors also offer sweeping lake views, as do the condos springing up all over the place. The Reefpoint Marina, Festival Park and Pershing Park can be accessed right after Highway 20’s terminus, along 4th and 5th Streets leading down to the water.
*** BREWERY ALERT ***
Just past the end of Highway 20 along Highway 32/Main Street, you’ll find the Racine Brewing Company, which established its Tap Room in a storefront in 2017. The Reefpoint Brew House is located just east of the end of Highway 20 in the busy Marina area; they don’t brew beers on site but do offer unique crafts that are contract-brewed by other breweries in southeastern Wisconsin.
Other things to see in Racine include the Johnson Wax Research Tower, the Johnson Wax Golden Rondelle (1525 Howe Street), built in 1964 for the New York World’s Fair; the Wind Point Lighthouse (4725 Lighthouse Drive, Wind Point), one of the oldest (1880) and tallest (108 feet) lighthouses on the Great Lakes; and the Racine Zoo (2131 N. Main Street, about 1.5 miles north of downtown), which offers an impressive array of animals – over 76 species – overlooks the lake, and offers its “Animal Crackers Jazz Series” on Wednesday and Selected Sunday evenings.
Want more details on Racine? Check out RealRacine.com!
From the relative bustle of Racine to the serene countryside, Highway 20 provides a good sampler of southeastern Wisconsin over a short distance. Plus, there’s Lake Michigan and kringle at the end!
Listen to our State Trunk Tour Podcast on Racine!
From Highway 20, you can run along Lake Michigan on Highway 32 up towards Milwaukee or down towards Kenosha, or head back out on Highway 11 to the west and southwest or Highway 38 to the northwest for an inland route towards Milwaukee. But definitely enjoy Racine as much as you can!
Events on this Tour
Enjoy some Friday night fun during Racine First Fridays in Downtown Racine from April - December from 4-9pm! It happens throughout the downtown area, centered on Monument Square where Highways 20 and 38 cap the ends of a main thoroughfare that is Highway 32. Socialize with friends and neighbors or even other road-trippers as you enjoy shopping, cool drinks and take a horse drawn carriage ride or stroll through the historic city streets. Join 50 plus independent downtown business owners as they welcome you to shop and dine locally while enjoying live music and discovering the best of Racine . . . Downtown! Come early & stay late. If you value a big event in a historic downtown, Racine First Fridays is worth the drive, especially on a State Trunk Tour route. First Fridays is a group of small business owners of boutique shops, restaurants, art galleries and museums who have worked together to put this event on nine times a year for 13 years. Businesses stay open late, put live music outdoors in three parks, have horse & carriage rides and an outdoor beer garden. Art galleries offer artist's demonstrations, restaurants offer specials and boutiques highlight new or favorite product lines. The sidewalks are filled with people and downtown is alive and vibrant. Also you could get FREE admission to the Racine Art Museum! In addition to First Fridays, check out the rest of downtown Racine. Right along the shores of Lake Michigan you can explore their marina, near the beach, zoo, Frank Lloyd Wright architecture and SC Johnson sites. Take the drive to where Highways 11, 20, 32, and 38 come together in downtown Racine. Enjoy happy people taking in the best of what downtown Racine has to offer! Check out the First Fridays website for more details.
Racine First Fridays Address:Monument Square 100 Main Street Racine, WI 53403 (262) 634-4287 Website