Highway 19 Trunk Tour

  • Western terminus: Dane County, at Highway 78 & U.S. Highway 14 near Mazomanie
  • Eastern terminus: Jefferson County, at the junction with Highway 16 on the east side of Watertown
Distance: 60 miles

Counties along route 19

  • Dane
  • Dodge
  • Jefferson

WIS_19“‘Trek’ between Watertown and Mazo”


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.


Few square inches of wall – or ceiling – at Rookie’s is uncovered by sports memorabilia.


Seriously. This is the bathroom at Rookie’s.

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 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.


Highway 19 threads its way through northern Dane County, with hills often lining its north side.

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.

waunakeesign_600Highway 113 joins up in Waunakee and rides with Highway 19 for about three miles before breaking south to Madison. On this stretch, atop some hills, the State Capitol is visible to the south; it’s about nine miles away and across Lake Mendota, but its dome and several of the high-rises on the UW campus come into view here on a clear day.

Octopi Brewing's 3rd Sign Brewery sampler

Samples of 3rd Sign brews at the Octopi Brewery in Waunakee.

Also, in the light industrial park shortly before Highway 113 breaks away, you can connect to Octopi Brewery, a craft brewer that brews for others along with a nice line of their own brands under the name 3rd Sign Brewing. Opened in 2016, their Tap Room offers a wide variety of samples and makes a good stop.


Meanwhile, we continue on Highway 19 east to the fast-growing crossroads on the south end of Windsor, where we meet I-39/90/94 – part of the longest triple-Interstate concurrency in the nation – and shortly thereafter U.S. Highway 51, the original north route from Madison.

Past tiny Token Creek we reach U.S. Highway 151, which now an expressway from Madison all the way to Fond du Lac. Ducking under the freeway bypass, Highway 19 heads into the heart of Sun Prairie (pop. 30,871), one of the fastest-growing cities in Wisconsin. 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.)


Jimmy the Groundhog doing his annual duty on February 2nd. (Photo courtesy of the Sun Prairie Chamber of Commerce.)


As Georgia O’Keeffe’s birthplace and childhood home, Sun Prairie proudly notes her history right along Highway 19.

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. On the east side of town 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.


Angell Park Speedway, a 1/3-mile dirt oval with a long history and the National Midget Racing Hall of Fame to boot. With noise that would scare a Who concertgoer, cars whip around and dirt flies at over 100 mph: yes, midget races are fun to check out!

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…


19pigwood_280hiOr 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.


The wooden roller coaster at Little Amerricka – it’s not one of the biggies, but it’s still fun. Duck if you’re really tall, by the way…


Little Amerricka has all kinds of rides, including carousels and trains, an easy way to have amusement park fun without much hassle or travel.

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.


Waterloo is the World HQ of this iconic bike brand.


And of course, TREK’s HQ has bike racks right out front.

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. Oh, and don’t forget the German host in an attempt to look like Napoleon introducing each member afterwards. You’ll see.

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.


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.


Amid a typical Wisconsin middle-class neighborhood on the southeast side of Watertown lies the historic Octagon House, built in 1854 to fulfill a whipped guy’s promise.


In case you want detail on the historic marker…

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.


Up for a malt, ice cream or other sweet concoction from an old-fashioned, authentic soda fountain place? Mullen’s Dairy Bar in downtown Watertown offers items for your taste buds and cool items to look at from the store’s early days.


The main drag in Watertown, which is Highway 19 – and was U.S. 16 until 1962. Today, this section is also “Business” Highway 16.

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(?)


A nice summer day along the Rock River in Watertown. Water levels can vary greatly – we’ve seen this park submerged before.

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!


Highway 19 ends as it merges into Highway 16 east of Watertown, heading towards Oconomowoc. Highway 19 once continued all the way to Milwaukee; it was truncated back to Watertown in 1947.

West Terminus:
Can connect immediately to: Highway 78, U.S. 14
Can connect nearby to: U.S. 12, about 7 miles east; Highway 60, about 8 miles north

East Terminus:
Can connect immediately to: Highway 16
Can connect nearby to: Highway 26, about 1 mile west

Tour Gallery

Events on this Tour

Route 19 Facts

  • • Highway 19 once ran from Sun Prairie all the way into Milwaukee from 1918-1947 before it was pulled back to end in Watertown.
  • • The Rock River runs through Watertown twice.
  • • While considered an unofficial "northern bypass" of Madison, Highway 19 may become part of an ungraded bypass in the near future.
  • • Waunakee lays claim to being the "only Waunakee in the world."

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