Quickie Summary: State “Trunk” Highway 19 skims the northern side of Madison’s metro area and connects to Watertown. Before 1926, Highway 19 once continued all the way west to Prairie du Chien and before 1947, all the way east to downtown Milwaukee. Today, Highway 19 serves as a key connector, part of which could serve as Madison’s north beltine sometime in the not-too-distant future. You travel through the only Waunakee in the world, check out the sun and the prairies around Sun Prairie, hit the HQ of TREK bikes, and more.
Wisconsin Highway 19 Road Trip
The Drive (west to east): State “Trunk” Highway 19 begins on the outskirts of Mazomanie (pop. 1,652), a charming little town in northwestern Dane County named after several incarnations of a combination of one of the Native American chiefs from the area and the term “iron walker” from when the railroad came through in the 1850s. Downtown Mazo, as many shorten the name to, features 34 commercial buildings on the National Register of Historic Places and in particular a cool railroad depot that went up in 1857 and has had only minor changes since. Budget Travel magazine named Mazomanie one of “America’s Coolest Small Towns” in 2008, noting its art galleries. There’s also a reference to the legendary “clothing optional” Mazo Beach nearby along the Wisconsin River – and the beach is real. We checked it out and hey, “when in Rome.” But we didn’t do pictures (you’d thank us, really.)
Anyhoo, on the east side of Mazomanie lies U.S. 14 and Highway 78… and a bar named Rookie’s, a State Trunk Tour favorite. Popular with baseball players (the owner of Rookie’s owns the Madison Mallards), bikers, drivers and craft beer aficianados, Rookies is what most other sports bars strive to be. Memorabilia is here in incredible abundance.
From the intersection with U.S. 14/Hwy 78, Highway 19 begins its path north and east across the fields and rolling hills of northern Dane County. Coupled with 78 for a brief spell, Highway 19 splits off and begins its trek east. Through much of this stretch, the road hugs the hill next to a valley along Halfway Prairie Creek, which is as appropriate a name as any, given the topography. Indian Lake County Park is one of the largest parks in Dane County, which is one of the largest counties in the state. The scenery here is pretty enough, but if time allows hit the walking trails and check out the historic hilltop chapel, which was built in 1857.
After about nine curvy miles, U.S. 12 shows up; Highway 19 joins it for about a mile and a half before heading east on its own again. Farms and a state marshland flank the road as you make your way into a uniquely-named town.
The town of which we speak? Waunakee (pop. 12,097). the “only Waunakee in the world”, as they like to point out. It was founded as Leicester in 1870; the following year, two early settlers persuaded the St. Paul Railroad – with some cash and land in hand – to relocate through their property instead of the original intended location two miles north. A post office and other buildings sprouted up, and the village incorporated as Waunakee (one Native American meaning: “the fair and pleasant valley”) in 1893. Waunakee is growing quickly, and its downtown is seeing redevelopment.
Highway 113 joins up in Waunakee on the town’s western side and rides with Highway 19 into the heart of downtown, which features a lot of older buildings and boutique shops along with a slew of newer developments, designed to bring in residents to downtown as well as more business. Where Highway 19/113 crosses the main railroad line downtown, you’ll see the old train depot; today, it holds the Visitor Center where you can get more info on the town.
On the other side of the tracks from the old train depot, you’ll find Lone Girl Brewing Company (114 E. Main Street, 608-850-7175.) Located in a nicely renovated building, Lone Girl opened up in 2015 and offers a variety of brews made within, along with a restaurant offering an extensive menu. On warm days and evenings, the rooftop opens up for movie showings, live music, games, and more beer sampling. Weather-proof are brewery tours, which are offered at various times, usually on Sundays. Lone Girl is open seven days a week, starting at 11am every day except Monday, when it opens at 5pm. It’s open all the way until 2am Thursday-Saturday, unless things are really slow. But with this brewery’s popularity, that’s not a common occurrence.
Heading out of Waunakee, Highway 19 rides some higher grounds that, on a clear day, affords glimpses of the State Capitol dome and several of the high-rise buildings on the UW-Madison campus, all about 8-9 miles away on the other side of Lake Mendota. A brief jump south on Hogan Avenue lets you reach Octopi Brewery, a craft brewer helping numerous brewers across Wisconsin meet their capacity needs. Opened in 2016, their Tap Room offers a wide variety of samples and makes a good stop. Shortly thereafter, Highway 113 does break south to head towards the capital city. Highway 19 continues to head eastward, towards the Interstate and Windsor.
About six miles later, Highway 19 reaches the increasingly busy crossroads around I-39/90/94, the longest triple-Interstate concurrency in the nation. At this point, you could jump on I-39/90/94 for fast access to Madison, Chicago, and Milwaukee to the south or La Crosse, Eau Claire, and Minneapolis/St. Paul to the north; but a more Wisconsin-y way to go would be to access the local cheese shop right within sight via County CV, the Mousehouse Cheesehaus. Under the same family ownership since 1988 but with origins as a cheese shop dating to the 1960s, Mousehouse offers over 300 varieties of cheese from over 40 cheesemakers. You can browse it all once you pass under the massive mouse perched on the roof (his name is Igor) and wave back at the welcoming mice in the entryway; their names are Maxine and McKenzie. Along with cheese (packs, curds, spreads, and more), Mousehouse offers homemade fudge, freshly-made sandwiches, wine, beer, t-shirts, books, knick-knacks, and other items that remind travelers that they’re definitely in Wisconsin. We do enjoy their summer sausage and swiss sandwich; sample some goodies and stock up on your cheeses before you continue your Highway 19 Tour!
Along with the Mousehouse and a slew of restaurants, gas stations, and a major Pepsi facility, Highway 19 meets U.S. 51, just east of the I. Highway 51, once the primary road north out of Madison, is nicknamed “Wisconsin’s Backbone” because it basically runs right up the center of the state; it’s a freeway briefly at this point too. A lot of people consider this the dividing line between the western and eastern half of the state.
As we reach this “eastern half,” you pass Token Creek, currently an unincorporated crossroads that we think will be a booming suburb before too long. But another booming suburb, while being a significant community in its own right, is coming up.
Past tiny Token Creek we reach U.S. Highway 151, which now an expressway from Madison all the way to Fond du Lac that bypasses the heart of Sun Prairie (pop. 30,871), one of the fastest-growing cities in Wisconsin. Highway 19 ducks under U.S. 151 and works its way downtown so you can experience the place.
Sun Prairie is a prognosticating town. Forget Punxsutawney Phil in Pennsylvania: Sun Prairie holds the official title of “Groundhog Capital of the World”, as noted in the Congressional Record. Jimmy the Groundhog makes his annual prediction in Sun Prairie on February 2nd. Why February 2nd, you might ask? Well, apparently it’s because that’s a “cross-quarter day”, normally the midway point between the Winter Solstice and the Vernal Equinox. Jimmy helped make national headlines when he bit the mayor’s ear in 2015 (hey, groundhogs don’t like waking up early, either.)
Along with Groundhog Day, Sun Prairie is known for being the native hometown of Georgia O’Keeffe, whose famous paintings continue to inspire and influence artists worldwide. Her parents’ names were Francis Calyxtus O’Keeffe and Ida Totto O’Keeffe, in case you were worried that Wisconsin dairy farmers who sire famous artistic offspring don’t have unique enough names.
Sun Prairie’s downtown includes The Cannery, a former canning factory that now houses apartments, restaurants, and shops. Rising above is the unique Columbus Street Water Tower, which went up in 1912 and features a design combining stone, metal, and wood. The Market Street Diner (110 Market Street, 608-825-3377) has an old-school and Art Deco feel (even though it’s not from the era originally) and serves up great classic diner food.
*** Brewery Alerts ***
Sun Prairie has become a brewing town, as so many of Wisconsin’s towns have. The city has two craft breweries, each within two blocks of each other in the burgeoning Cannery District downtown. Full Mile Beer Company & Kitchen (132 Market Street, 608-318-2074) focuses on locally-sourced ingredients for all their brews and their kitchen offerings, which they describe as “comfort foods with a twist,” often making use of their Mugnaini wood-fired oven for pizza and perhaps a few other menu items. The beer selection there is a vast, all brewed on-site in their 10 barrel, three-vessel brewhouse. If you prefer spirits, they offer a wide selection there, too. You’ll find Full Mile two blocks off Highway 19, within eyeshot via Market Street by the heart of The Cannery district.
Meanwhile, right along Highway 19 at 239 E. Main Street, you’ll find Right Bauer Brewing Company. Located in a narrow downtown storefront, Right Bauer uses many terms from the card game Euchre, of which founding brewer Martin McNally and his wife Erica are big fans. Right Bauer opened in October, 2018 and brews a variety of styles with five or six of their own beers offered at any given time along with 5-10 carefully selected craft brews from others around the area. Right Bauer’s kitchen smokes up a lot of meat for BBQ offerings, along with fried cheese curds (made with Muenster, an awesome way to do it) that are great on their own or as part of a poutine dish. Based on our most recent visit, we recommend the Peaches & Cream IPA and the Nitro Milk Stout, but hey – that’s up to you.
On the southeast edge of downtown is Angell Park, home to longtime dirt racing track Angell Park Speedway. This 1/3 mile oval dates back to 1903 and has been racing midgets since 1936. Drivers like Stan Fox and Jeff Gordon have competed on the track, and its illustrious history led it to being home to the National Midget Racing Hall of Fame. Open during the racing season, over 120 inductees are showcased including drivers like A.J. Foyt, Parnelli Jones and Ron “Sleepy” Tripp, who got his nickname because he would often fall asleep in the cockpit of his racer waiting for the next race to begin.
The stretch of Highway 19 between Sun Prairie and Marshall was designated by the Wisconsin State Legislature as the “Georgia O’Keeffe Memorial Highway” in 2007.
There’s no shortage of interesting roadside views on this stretch of Highway 19. A colorful design on a barn, for example….
Or a tin man perched in front of an HVAC service company…
Or whatever the hell this thing is all about…
After a few more miles, Highway 19 reaches Marshall (pop. 3,432), known in previous incarnations as Bird’s Ruins (after fire destroyed buildings during in 1838 as the village was getting established) and Medina. Located along the Maunesha River, Marshall is tucked into the northeastern corner of Dane County and is increasingly headed towards “suburban bedroom community” status. Downtown features a crossroads with Highway 73. Marshall has a permanent seasonal amusement park known as Little Amerricka, which features rides, a Moonwalk, a carousel, a small roller coaster, and even a mini-train ride called the Whiskey River Railway. It’s a fully operational 1/3-size railroad that rides along 3 miles of track on a tour.
Past Marshall, Highway 19 ducks into Jefferson County and heads into ABBA’s favorite Wisconsin town, Waterloo (pop. 3,259). Like Marshall, Waterloo is on the Maunesha River in the far corner of a county: this time, it’s Jefferson. Waterloo is the home of Trek Bicycles, and you pass its headquarters coming into town on the west side. Waterloo is also the home of Van Holten’s Pickles, innovator of “pickle-in-a-pouch” and today the world’s largest producer of individually-wrapped pickles. Heading into downtown, you meet up with Highway 89, which joins Highway 19 through town before breaking away towards Lake Mills.
A special State Trunk Tour salute to Waterloo from ABBA
Okay, we couldn’t resist. When I think of Waterloo, I think of the song..and it’s a fun driving song anyway as long as nobody’s watching.
So, straight from German television in 1974, courtesy of YouTube, enjoy this riveting performance of ABBA’s “Waterloo”, complete with sort-of dancing, lip-synching and fake instrument-playing to the song. And the outfits… well.
Meanwhile, Highway 19 heads a but northeast into Dodge County and tiny little Portland, which has 3 more bars than the Town of Portland in Monroe County (thanks to State Trunk Tour reader Anthony from Waterloo for that one!), and from there Highway 19 cuts through Waterloo State Wildlife Area and the humble hamlet of Hubbleton, threading more or less along the Dodge-Jefferson County line.
Yes, another craft brewery along or near Highway 19! And since nobody just happens to drive past Hubbleton Brewing Company (W10445 Hubbleton Road, Waterloo, 920-253-7141) we decided it should be pointed out here. Following County BB north to Hubbleton Road and heading east briefly, you’ll find this fledgling brewery on the Schey family farm – next door to their house after a long ride up their driveway. The family farm and residence also includes a three-acre hop farm. The hops are used in their beers and are also sold through a collective called Arrowhead Hops; founder and master brewer Dan Schey was also founder and first president of the Wisconsin Hop Exchange, which manages the hops of more than 65 growers in southern and central Wisconsin. The brewery itself is behind the tasting area. Hubbleton Brewing uses a 3-barrel system and plans to expand to 10, especially as they break ground on their new, larger space later this year. Tours, which don’t take long, are available on Saturdays and upon request, as Dan will proudly show you their layout.
Back to Highway 19, the drive east continues toward the newer Highway 26 freeway bypass of the town that launched a school grade and has a river running through it – twice.
Watertown (pop. 21,598) is next up and Highway 19’s final city. Watertown was the second-largest city in the state back in 1855 and launched the first kindergarten in 1856. It can be found – and toured – on the grounds of the Octagon House, an 1854 structure built by one of the city’s founders, John Richards, to fulfill a promise to his sweetheart (he promised to built her the finest house in Wisconsin Territory if she would marry him. This was before the days of just using a stadium message board to ask.) The “water” in Watertown comes from the Rock River, which winds through the city. Twice.
Highway 19 is also Main Street in Watertown. After crossing Highway 26, you’re on both 19 and Business Hwy. 16. Watertown’s downtown is fairly extensive and features a number of shops, along with Mullen’s Dairy Bar, a great throwback malt shop-type place that opened in 1931. An aggressive Main Street program is paying off and walking around, back and forth over the Rock River, is a great way to stretch your legs as you check out everything from clothing stores to taverns and historic bank buildings.
The first crossing of the Rock River is downtown where all the murals are; the second crossing is on east side of town at a park where walking trails, pedestrian bridges, and even fishing piers with carp-specific disposal bins are available(?)
Highway 19 is a relatively brief and pleasant drive, which makes for a good afternoon. You have good access to and from Madison, Milwaukee and points in between, as well as a series of other State Trunk Tour routes. Enjoy!