July 14, 2024
Highway 27 between Rising Sun and Fairview


STH-027“Whipping and Winding Down Western Wisconsin”


WisMap27Quickie Summary: For the Wisconsin Highway 27 Road Trip, State “Trunk” Highway 27 runs for almost 300 miles from the wilderness of Brule River State Forest near the Lake Superior shore, through a slew of rural towns, up, down and around western Wisconsin’s rugged landscape, all the way to the banks of the Mississippi River in Prairie du Chien. Scenery, serenity and small-town charm abound on this route from top to bottom.

Wisconsin Highway 27 Road Trip

The Drive (North To South): Highway 27 begins at U.S. 2 in Brule (pop. 607) at the edge of the Brule River State Forest. Now, you may also know that there’s a Brule River on the Wisconsin-Michigan U.P. border on the northeastern edge of the state. This is not the same river; this one is officially the Bois Brule River (but locals refer to it simply as the “Brule”), which runs from Upper St. Croix Lake into Lake Superior. Speaking of, Highway 27 is only about 15 miles from Lake Superior at its northern start; at times along U.S. 2 nearby, you can still see the lake and the sizable Iron Range hills in Minnesota. So you’re almost as far north in Wisconsin as you can get. Not surprisingly, logging and fishing are two primary activities around here.

The River of Presidents. The Brule River is also known as the “River of Presidents”. Presidents Coolidge, Cleveland, Hoover, Truman and Eisenhower came here regularly to fish and hang out, far away from the craziness around D.C. This is also a huge area for fly fishing, and the river is one of the preeminent trout streams in North America. And yes, fish fry Fridays are quite popular here. You can sample a Brule fish fry at Kro Bar & Grill (13920 E. Hwy 2, 715-372-4876), River House Restaurant (13844 E. Hwy 2, 715-372-5696) or at the Twin Gables Cafe (Corner of Hwy 2 & 27, 715-372-4831). Wild rice is another popular local item, and all through Douglas County you’ll find wild rice available for sale.

From Brule, Highway 27 cuts through the Brule River State Forest, into Bayfield County (the largest county in Wisconsin, although it doesn’t have a single traffic light.) Recreational opportunities continue to abound, thanks to numerous lakes that make up the Eau Claire Chain of Lakes: 11 connected, spring-fed lakes surrounded by an abundant forest of large pine and hardwood trees. These lakes make up the headwaters of the Eau Claire River, which flows into the St. Croix River at Gordon and prove you’re over the subcontinental divide and waters now flow to the Mississippi and the Gulf of Mexico.

Beyond this particular recreation paradise, Highway 27 heads into Sawyer County before hooking up with Highway 77 and getting into Sawyer County’s county seat.


Hayward, Wisconsin welcome mural

Hayward (pop. 2,129) is one of northwestern Wisconsin’s most popular vacation destinations, being located amidst a vast array of lakes with some of the country’s best fishing, forest in every direction, and a knack for hosting a series of participatory events (Birkie, anyone??)

Hayward is home of the American Birkebiener – and several fast food restaurants. Don’t laugh; there aren’t many anywhere else nearby! The downtown area has many structures with second level balconies, used during the Birkie for spectators watching cross-country skiers plying the main streets.


Like many Wisconsin towns, there are a lot of good eats and drinks all over the place. Those familiar with Famous Dave’s locations around the country might be interested to know that it all started in Hayward. Famous Dave of the Lac Courte Oreilles Ojibway Tribe opened the first Famous Dave’s here in 1994, serving up barbeque on garbage can lids (yes, the portions can get huge) and their award-winning bread pudding with praline sauce. Sadly, the original location here burned in 2014.

*** Brewery Alert***
Along U.S. 63 less than a mile southwest of Highway 77 lies an old brick building that simply says “Brewpub” on the side… at least that’s the only part you can see from the street. Inside is the Angry Minnow Restaurant & Brewery (10440 Florida Ave./U.S. 63, 715-934-3055). The building itself was constructed in 1889 and once housed a sawmill operations office; today, it’s probably the nicest restaurant in Hayward, with rich, dark wood and brick everywhere. The oval-shaped bar and iron chandeliers help create a cozy, warm atmosphere. The food is terrific (try the Black Pepper Seared Tuna appetizer) and the craft beers are quite good.

Lumberjack Championships, Birkie Skiing and the World’s Biggest Musky. Hayward does it up in every season. The annual Lumberjack World Championships hold events in Hayward, so expect lots of axes, saws and flannel. Scheer’s Lumberjack Shows are highly recommended. Watch lumberjacks “speed climb” up trees, throw axes (not at you, don’t worry), and perform things like logrolling and canoe jousting. Can you get more up North than this?? In February, Hayward hosts the American Birkebeiner, an annual cross-country skiing race from Cable (30 miles away via the trails) to the “main street” block in Hayward, just off U.S. 63 several blocks southwest of where it intersects with Highway 77. About 9,000 skiers participate every year. About 2,500 bikers head through the wilderness every year in the Chequamegon Fat Tire Festival; it’s one of the most popular off-road bicycling events in the nation. And trust me, when you wander into town doing the State Trunk Tour on that weekend, the hotels are full and/or pricier than normal. So watch the Events calendar here carefully! The National Freshwater Fishing Hall of Fame (715-634-4440) is probably the most consistently visible (100,000 visitors per year) attraction, thanks to the World’s Largest Muskie. Standing 143 feet long and 41 feet tall, the muskie holds names of world record-holders in fishing across the world. You can check out the names and climb the steps to show yourself from the muskie’s mouth, 4 stories off the ground. It’s a popular place to get your picture taken… how can one resist??

The World’s Largest Muskie – and that’s just the start of what you can check out the National Freshwater Fishing Hall of Fame!

Check out our full gallery of photos at the National Freshwater Fishing Hall of Fame here!

Leaving Hayward, Highway 27 meanders south past a variety of lodges and recreational areas. Access to snowmobiling, hunting and fishing is nearly omnipresent in these parts. Southward on Highway 27, long stretches through forest and between lakes dominate for many miles in a row before 27 meets up for short stretches with several other highways. Highway 70 meets up with 27 as you approach and turn along lovely Sand Lake, which despite the name consists primarily of water.

The kind of scenery along Highway 27 between Hayward and Radisson.

Following Highway 27 & 70 means winding along a series of lakes and rivers, affording sometimes brief but always lovely views. The scenery here appeals to everyone, even old Chicago gangsters like Al Capone, who kept a hideout on Pike Lake (via County Highway CC) a few miles north of Couderay (pop. 96 on the sign, it has since dropped to 88), a blink-of-an-eye village along the highway. There are no retail businesses in Couderay, although there is a part-time tavern. Nevertheless, it has its own post office serving the surrounding area (the zip is 54828, in case you were curious) and it’s one of the tiniest, charming post offices you will ever see. Constructed of native stones, it’s located next to what at the time of this writing is a wreck of a building constructed with similar materials, but is missing a roof and most of its walls. Research tells me this used to be a place called the Keystone Bar, but if anyone is positive, let us know.

State Trunk Tour Tidbit:
The coldest temperature ever in modern-day Wisconsin, an innards-chilling -55°F, was reported in Couderay on February 2nd and 4th, 1996.



Check out Couderay’s (population 96) post office, right along Highway 27/70. Some of the adjacent buildings have since been abandoned, making for some interesting perspective shots.

Further east, the northern terminus of Highway 40 crosses your path at Radisson (pop. 222 and ironically, there is no Radisson Hotel to be found) before the Chippewa River shoulders up to parallel your way. At Ojibwa, Highway 70 continues east toward Winter and Minocqua while Highway 27 turns south again for its next lone stretch, a long and straight haul that runs for 23 miles into Rusk County.


At the crossing with U.S. Highway 8, Highway 27 grazes the lovely city of Ladysmith (pop. 3,932). Ladysmith was founded in 1885 as “Flambeau Falls” reflecting its picturesque location along the Flambeau River where the new Soo Line railroad made its crossing. Subsequent names included “Corbett” and “Warner” before “Ladysmith” was settled upon in 1900, after the bride of a man named Smith who ran an influential local company (apparently, she was quite a lady). The Flambeau Mine Trails offer a great glimpse at a reclaimed mine. For eight years in the 1990s, this site was a wide-open copper and gold mine. The valuable minerals may be gone, but today the 181 acres provide scenic open grassland – a rarity in these relatively dense-forested parts – and excellent bird watching.

Ladysmith features a lot of lovely old stone buildings and a fair amount of artwork coloring some of them, including art that welcomes you along U.S. 8, just east of Highway 27. Large wooden bears adorn a city park along the Flambeau River in Ladysmith. Real bears prove to be more intimidating.

Ladysmith is the county seat of Rusk County, which features over 300 miles of snowmobile trails and serene, productive fishing in the Flambeau and Chippewa Rivers, which coverge in the southern part of the county. Equestrians can take advantage of the Copper Park Equestrian Trails, which cover about 10 miles of trails for hikers, horseback riders and others not in need of motor for a while. The trails are part of the Reclaimed Flambeau Mine Site (check out this website… it’s an aerial view that shows when it was a mine versus how it is today), an area featuring a number of things to do. The whole kit ‘n kaboodle is along Highway 27 about a mile and a half south of Ladysmith, between Jensen Road and County P.

Heading south, it’s a pretty straight shot into Chippewa County, where you get nice water views crossing the Holcombe Flowage (which flow into the Flambeau) and, before long, there’s actually a curve: you meet Highway 64 and join it westerly into a town originally named Brunet Falls after an adjacent island in the Chippewa River. Today, it’s called Cornell (pop. 1,466), and it’s home to the only known pulpwood stacker in the world. Standing 175 feet high, it looks like a crane about to build something, or a radio tower leaning at about 45 degrees.


Cornell features the only known pulpwood stacker in the world (hey, making it the world’s largest!) In use from 1913 until 1972, it apparently stacked a lot of pulpwood.

Cornell also supports a local municipal airport, ample recreation with Burnet Island State Park on the northwest side of town, and is the northern trailhead for the Old Abe State Trail, one of Wisconsin’s awesome rail-to-trail projects. This one follows along the Chippewa River about 20 miles to Lake Wissota State Park near Chippewa Falls and is paved much of the way.

After the run through Cornell, Highway 64 breaks away west across the Chippewa on its way to Minnesota. Meanwhile, Highway 27 heads south again, crossing the 45th parallel into Cadott (pop. 1,345), named after a French fur trader. Cadott hosts a number of music festivals that draw from all over the Midwest and the nation, including Country Fest in June and Rock Fest in July, each of which draw tens of thousands.

At the interchange with Highway 29 on Cornell’s south side, you’ll find the Wisconsin Veterans Tribute. Part of the River Country Plaza Truck Stop at the exit, you’ll find many significant memorials, an AH-1S helicopter, cannons, markers and more all under an eye-catching cadre of flags from all over the world.

The flags of the Wisconsin Veterans Tribute, at Highways 27 & 29 in Cadott.


Cadott lies along the 45th parallel, halfway between the Equator and the North Pole (although the weather is more like the North Pole than the Equator much of the year). This is one claim to fame Cadott wants you to know about as you enter town.

South from Cadott, Highway 27 heads through the small settlement of Ludington and then past Lake Eau Claire and its popular Lake Eau Claire County Park, which offers a lot of nice amenities near and along the shore of the lake for which it was named.

Great photo ops await a few more miles ahead at the Dells Mill & Museum (E18855 County Road V, Augusta, (715) 286-2714), a beautiful historic mill that was constructed back in 1864 along the Dells Millpond. One of the most popular photography shots in Wisconsin can be taken here, overlooking the mill, its waterwheel, and the waterfall that powers it. Yes, we used the present tense “powers” – it can still operate! It’s the oldest mill in Wisconsin still running, so we can say it’s ground a lot of wheat and flour in its time. The museum is open May through October, but the grounds are open year ’round. Hours at the museum can vary, so it’s best to call ahead at (715) 286-2714.


About three more miles down the road you hit Augusta (pop. 1,550), where Highway 27 meets up with U.S. 12. Augusta, named after the capital of Maine, is in the heart of an area with many nearby Amish settlements, and the wares produced by these communities can be found in stores in town. If you’re hungry, Gup’s Drive-In offers some classic roadtrip fare in season, and the nearby Gene’s Black Bear Supper Club offers a longer dining experience if you’re ready to kick back. Augusta is also the kick-off spot for the Falling Leaves Art Tour, which usually takes place in early October; it’s a self-guided tour of art studios and scenic areas that allow for maximum enjoyment of the area in autumn.

*** Fairchild to Black River Falls is coming soon… meanwhile Black River Falls to Sparta continues below! ***

Black River Falls

Black River Falls (pop. 3,618) is the county seat of Jackson County, with hydroelectric dams capturing the power of the Black River as it winds through town. Being by far the largest town in the county, it has a sizable downtown area and quite a few interesting, colorful murals that capture the area’s history and points of interest. U.S 12 and Highway 27 meet up with Highway 54 on the heart of downtown at the river; I-94 carries most of the traffic along the city’s eastern edge.


Highway 27 runs right through Downtown Black River Falls.



State Trunk Tour Tidbit:
In 1872, Black River Falls became the first village in Wisconsin to establish a free city library.

sphagnummoss_500Ever heard of Sphagnum moss? Me neither, but it’s actually a significant plant that pumps money into the local economy. Growing quickly in the boggy and marshy lands in the area, Sphagnum moss is used to keep nursery plants and flowers alive and watered during shipping, since this moss can hold 20 times its weight in water. It’s used in hydroponic gardening, which I had to look up — it’s basically about growing plants with mineral nutrient solutions instead of the traditional soil. It’s even used for surgical dressings because it is sterile (ironically, it reproduces quickly.) It also helps prevent fungus attack in seeds. Wisconsin is actually the only state that produces Sphagnum moss commercially.

The Black River, which runs through the heart of Black River Falls (logically enough), indeed has a blackish hue due to its high iron content. It’s a popular paddling and canoeing river. The Black River Falls Chamber of Commerce offers information on a bunch of other places to take advantage of the river’s amenities, as well as the city’s. You’ll find it approaching downtown, shortly before the junction with Highway 54. You can also call them at 800-404-4008.



*** Brewery Alert ***
Black River Falls is home to Sand Creek Brewing Company (320 Pierce St., 715-284-7553), which makes a variety of quality brews on a site that started brewing beer in 1856 – it’s had a wild history since. Brewing here actually took a 75-year hiatus until the Pioneer Brewing Company started up in 1995 and became the new home of Sand Creek Brewing in 2004. For more history, check out this page. Meanwhile, stop in (right off Highway 54) and check out their brews, from the light Golden Ale to the hearty Sand Creek Imperial Porter. State Trunk Tour picks include the Groovy Brew, Woody’s Wheat (banana overtones are a good thing) and the Pioneer Black River Red, which won the World Beer Cup’s Gold Award for a German-style Marzen in 2000.

Cool kitsch: Familiar with the British band The Fall? They actually mention the Black River Falls Motel. Why? I’ll do some digging and find it, ’cause I’ll bet the story’s interesting. Also, a quick ride east on Highway 54 will reveal the orange moose at the SureStay Plus Hotel Black River Falls (long called Arrowhead Lodge & Suites) and the “cow” McDonald’s, a Mickey D’s with cow-like themes on the tables – although they could be dalmation-like, too. The Majestic Pines Casino is also nearby, just east of Black River Falls. If you’re feelin’ it, stop in and test Lady Luck.

The Legend of the Orange Moose
54moose2_lgThey proudly call it the world’s most unusual town ornament. Legend says a Norwegian farmer named Torvaald Kjorvak (try pronouncing that) found a wounded moose calf along the Black River. With no mother around to be found, Kjorvak nursed the animal back to health himself. He then fed him an experimental grain that helped him grow huge… and orange. Find out more here!

In Black River Falls, U.S. Highway 12 breaks away and parallels I-94 on its way to Tomah. Highway 27 continues south through the Black River State Forest, where a stop to hike up Castle Mound is a terrific way to get both exercise and a phenomenal view. You can camp, ski, ride ATVs, or just relax and check out the abundant wildlife. If you want to check out some cranberry bogs (this is the edge of Wisconsin’s “Cranberry Country”), take a brief jaunt down Cranberry Drive for about a mile and a half.

After Cataract, Highway 71 joins in from Melrose. Just a few hundred yards west on Highway 71 brings you to Wegner Grotto County Park, a nice art display of concrete sculptures decorated with glittering pieces of glass, seashells, Indian arrowheads, and other augmentations.

sparta_wegnergrotto01 sparta_wegnergrotto02

Above: A mere sample of the concrete and glass artwork on display at Wegner Grotto.


For about ten miles, Highways 27 and 71 stick together before reaching Sparta (pop. 8,648), the Bicycling Capital of America. Sparta is the main town for about twenty miles around; that coupled with hosting Fort McCoy and the bike tourists means a commercial strip through town where you can get just about anything. Highway 27 meets with Highway 16 on this strip, where Highway 71 breaks east to go follow the Elroy-Sparta Trail route. Highway 21 also starts just to the east in the heart of Sparta’s downtown; Highway 27 stays on the west side and meets I-90 on the south side of town.

Sparta lies at the connecting point of the Elroy-Sparta Trail – which originates 32 miles away in Elroy (of course) – and the La Crosse River Trail, which heads toward La Crosse and the Mississippi River. The trail meets at Sparta’s old train depot, which offers both energized and tired bicyclists whatever they need.

At the Sparta Depot, a group of bikers begin the 32-mile trek toward Elroy.


The town’s enthusiastic support of bicycling extends to street name signs that bear bike symbols. Numerous motels and B&B’s cater to the cycling crowd while downtown establishments offer supplies for your bike and sustenance for your tummy.

Of course, you can’t top having the World’s Largest Bicyclist to exemplify your status as America’s Bicycling Capita, right? Roll east slightly along Wisconsin Street (Highway 16) and you’ll find Ben Bikin, a 32-foot high fiberglass statue. Ben sits atop an 1890s-era bicycle, cementing the city’s status and getting everybody driving, riding, or walking by to look up and take notice.


Made locally, “Ben Biken” greets you to the Bicycling Capital of America along Highway 16/71, just east of Highway 27. He’s the World’s Largest Bicyclist!

The Deke Slayton Museum, chock full of bikes and space exhibits.

On top of bikes, Sparta has a number of attractions. Some kids who grow up in Sparta leave for big cities; Deke Slayton left for Earth’s upper atmosphere. The Deke Slayton Memorial Space & Bicycle Museum honors the astronaut, native son, and head of NASA Operations from 1963 to 1972. And that fiberglass hippo, whose mouth you putt golf balls into while playing mini-golf? Chances are, it was made in Sparta at the FAST Corp. (FAST stands for Fiberglass Animals Shapes and Trademarks.)

spartaphantFAST does business all over the world, and few companies like it exist. A drive into their lot yields a sprawling field filled with fiberglass fun: large cows, alligators, elephants that double as childrens’ slides… the list goes on. You may traverse the field and marvel at their creations, as long as you behave and don’t climb on anything. Their lot can be found by following Highway 21 to the northeast edge of town, at the junction with County Highway Q. Look for giant fiberglass things.

FAST’s work is particularly evident in its hometown. The statue of a man on a bicycle that announces your entrance into Sparta along Highway 71 and the Clydesdale outside of the local Budweiser distributor are just two of the many pieces you can find in the area.

Sparta High School along Highway 27
Sparta High School’s mascot? The Spartans, of course! Michigan State alums, take note.

After crossing the intersection with Highways 16 and 71 and then getting through the hordes of gas stations and hotels from there to the interchage with I-90, Highway 27 continuing south begin to dive into the heart of Wisconsin’s gorgeous Driftless Area.

Highway 27 winding south of Sparta.
Highway 27 south of Sparta, ready for more Driftless Area scenery.
Farm and silo close to Highway 27 in Monroe County
Vistas of hill-framed barns (some quite close to the road) adorn this stretch of Highway 27.

Highway 27 continues to navigate the beautiful hills and valleys of southern Monroe County, through little Leon and making an easterly bend through the Leon Valley along the Little Lacrosse River to Melvina (pop. 104) before bending back west a bit on the way to Cashton (pop. 1,102).

Juusto Cheese at Pasture Pride along Highway 27 in Cashton, just south of Highway 33Just west of downtown Cashton, Highway 27 meets Highway 33, where you can stop and stock up on more cheese. Pasture Pride Cheese (608-654-7444) is right along Highway 27 just south of 33, and they offer a variety of cheeses using milk from Amish farmers – of which there are many in the area – going all grass-fed for their cows and goats. Pasture Pride is the home of that “Juusto” Cheese, the baked Finnish style of cheese that looks baked and is extra buttery in flavor – that’s what the judges who shower them with awards generally say.

Cashton is also the birthplace of Frank King, cartoonist and creator of Gasoline Alley (he gre up in nearby Tomah), as well as the birthplace of Leif Erickson. No, not that Leif Erickson, the one who became a justice on the Montana Supreme Court. But we’re guessing having that name helped with an air of authority.

Westby & the Ski Jump

Just past Cashton, Highway 27 enters Vernon County. Just past the little settlement of Newry, you just might see something poking above the hills on the horizon to the west-southwest. Is that… a … ski jump?? Yes it is! The Snowflake Ski Jump opened in 1961 and – right there in Timber Coulee a few miles off Highway 27 – hosts national and international competitions for ski jumping in January and February. Numerous Olympians have trained or competed at Snowflake, which is the 7th highest such jump in North America. Additional, smaller jumps are right there too, for junior competitions and training. Snowflake also opened a golf course to complement their ski jump and also their Rod & Gun Club, so Snowflake operates all year long. It can boast of having “the only nine-hole golf course in the shadow of an Olympic-sized ski jump.” If you want to check it out, follow County P west from Highway 27 about three miles south of Newry.

Past the jump, you hop into Westby (pop. 2,271), where Highway 27 meets up with U.S. 14 & 61 before heading into the heart of town. A city build on Norwegian heritage, Westby hosts one of the state’s largest Syttende Mai festivals each May and offers boutiques like the Uff-Da Shoppe along the main drag.


After hooking up with Highway 82, Highway 27 heads into Viroqua (pop. 4,335). The name can also apply to a genus of jumping spiders, but this Viroqua is a pleasant town where numerous artists have made home. Butch Vig, member of the rock band Garbage and producer to albums like Nirvana’s Nevermind and the Smashing Pumpkins’ Siamese Dream, was born in Viroqua, as was President Bush’s (the Dubya one) personal physician. Four main routes run through the heart of Viroqua, and all combine through downtown: U.S. 14, U.S. 61, Highway 27, and Highway 82.


The Fortney Building (above) includes a residence hotel and is a prime example of the early architecture along Viroqua’s Main Street, of which Highway 27 is one of four State Trunk Tour routes. The Temple Theatre is a 1922 Classic Revival style vaudeville and movie theatre that underwent a $1.3 million restoration; today it stands as a prime example of why Viroqua’s downtown is on the National Register of Historic Places.


Viroqua was called “the town that beat Wal-Mart” by Smithsonian Magazine in 1992, not because it prevented a Wal-Mart from opening, but because so many local businesses are successfully co-existing with it. Viroqua’s natural beauty has drawn artists for decades, but the arts and culture scene has been growing more significantly as of late. The presence of the renovated Temple Theatre and numerous coffee shops and galleries are just a hint of the growing arts community. Highway 27 goes through the middle of it all; architecture buffs can enjoy the theatre, the Fortney Building (pictured above), and the Sherry-Butt House, an 1870 structure constructed in the Southern style… all of which are on Main Street.

14276182sign_225hiHighway 27 is just one of the routes on Viroqua’s Main Street. Highway 82 and U.S. 14 & 61 also travel through the heart of town. Highway 56 intersects downtown, too. Bypass plans were in place for many years that would carry some or all of the routes around town, but that got cancelled in 2014. And we’re pretty glad to see that – this is a town to explore!

South of Viroqua, the four highways stay combined for a few miles before Highways 27 and 82 break away to the southwest. You run a series of ridges, from which the views get quite expansive. You pass through the small village of Liberty Pole, which is noted for nearby Monument Rock, a huge natural rock formation (we’ll have to get a picture on the next trip through). From Liberty Pole west to Red Mound, you’ll see a series of old stone wayside markers. These markers note historical facts about areas in Vernon County, especially as they applied to settlement and clashes with Native Americans. Many of these markers were carved in stone in the 1930s; most have been moved to their current location. They’re worth stopping and checking out, especially if you’re a history buff. These markers are noted in points all along the route in Vernon County.


Above: Just southwest of Viroqua, this caboose (presumably in someone’s yard) lies on real railroad tracks. Several other sculptures adorn the property. Below: Liberty Pole, Wisconsin. Not a bustling metropolis, but a serene place to stop, step outside and enjoy the views and quiet sounds of southwestern Wisconsin.


Liberty Pole is also the name of an annual scenic motorcycle parade covering areas across this part of the state. Check out their home page here for more information.


As shown above (click for larger images you can read), county historical markers dot the sides of Highway 27 from Liberty Pole west for quite a ways. A map of marker locations is provided at most waysides, with specific details carved into stone tablets. John McCulloch is considered the county’s first European settler, building a cabin here in 1844 before “California Dreamin'” took him out west. Most of the tablets were made around 1930.

This area of Highway 27, basically between Viroqua and DeSoto, is big on scenic views and short on facilities, so make sure your gas gauge isn’t reading close to empty. Keep your camera ready, though! Highway 82 splits off at Fargo (not relation to the movie or North Dakota) and heads west toward DeSoto. Highway 27, meanwhile, turns south into Crawford County to run more ridges in this hilly territory.

And the beauty just continues on this stetch of Highway 27. The first settlement is the unincorporated Rising Sun, Wisconsin, supposedly named by a settler in 1856 who was super excited after seeing the sun after a rainy, cloudy two-week stretch (not an uncommon occurrence in this state.) Past more ridges are towns like Fairview and the village of Mount Sterling (pop. 211), named for platter and State Assemblyman William Sterling (who platted the town), not Roger Sterling from the Mad Men series – we surmised that possibility for a while. Highway 171 intersects here, ambling east and west across the territory.

Highway 27 between Rising Sun and Fairview
Part of the rolling hill farmland scenery as Highway 27 heads between Rising Sun and Fairview in northern Crawford County.

Meanwhile, Highway 27 starts heading southwesterly again, winding through Seneca (with 893 people, it’s the largest settlement between Viroqua and Prairie du Chien) and Eastman, where Highway 179 meets up.

It’s more ridge-riding after Eastman, where Highway 27 affords views that at times can include a glimpse of the Mississippi River from Limery Ridge, about six miles east of the river itself – giving you an idea of how high these ridges are.

Mississippi River in the distance through valleys from Highway 27 northeast of Prairie du Chien
That would be the Mississippi River about 5-6 miles away, visible from Highway 27’s vantage point near Limery Ridge. Iowa is in the distance, Prairie du Chien lies ahead on the route.

From this high vantage point, we begin a gradual and curvy descent into our final stop on the Highway 27 State Trunk Tour.

Prairie du Chien

Prairie du Chien (pop. 6,018) is the Crawford County seat and Wisconsin’s second oldest city (Green Bay is the oldest, in case you were wondering.) The Fox and Sauk tribes were here for hundreds of years prior to French explorers arriving and saying “voila!” Early establishment began in 1673 as Father Marquette and Louis Jolliet paddled their way to the Mississippi via the Wisconsin River and opening the area up for further European exploration. The first trading posts were developed in 1685 by French explorer Nicholas Perrot. Fur trade, along with Prairie du Chien’s natural location near the Wisconsin River and Mississippi River confluence, guaranteed the small settlement would prosper for years to come. Prairie du Chien’s history spans five centuries, including the only Wisconsin battle in the War of 1812, the Siege of Prairie du Chien. PDC’s first fort, Fort Shelby, was built by Americans built captured by the British in the War. By 1816, it had been replaced with Fort Crawford. The Black Hawk War, which took place in 1832, featured a commanding officer in the form of Colonel Zachary Taylor, who later became 12th President of the United States. A lieutenant during the same time named Jefferson Davis not only married Zachary Taylor’s daughter (named Sarah “Knoxie” Taylor, proving cutesy nicknames existed in the 19th century), he later became President of the Confederate States of America. Neither worked out well; the future President Taylor didn’t approve and poor Sarah passed away from pneumonia only months after their 1835 marriage; his new country in the 1860s didn’t last very long, either.

The fur trade may have kept many warm, but it made a few millionaires on top of it. Local resident Hercules Dousman was the first millionaire in Wisconsin, and in 1871 his son H. Louis Dousman built Villa Louis, a National Historic Landmark on St. Feriole Island. The plot of land upon which Villa Louis stands once held Hercules Dousman’s original house, as well as Fort Crawford and Fort Shelby. Today it’s a museum operated by the Wisconsin Historical Society, the first historic site for the organization.

Villa Louis mansion
The Villa Louis mansion, just part of what lies in store on the grounds of this National Historic Landmark on PDC’s St. Feriole Island.


Did school ever feel like prison? Well, Prairie du Chien has a prison that was once a highly-regarded Jesuit boarding school. Campion Jesuit High School operated from 1880 to 1975 and counts among its alumni the likes of Vicente Fox, Mexican president from 2000 to 2006; George Wendt, Norm of Cheers fame, a number of movies and noted Bearssss Superfan Bill Swerski; sportscaster George Blaha; former Wisconsin governor Patrick Lucey; and politician and prankster Dick Tuck (yes, his real name.) As long as we’re name dropping, Pat Bowlen, longtime owner of the Denver Broncos, was born in Prairie du Chien – one of the few Wisconsin natives who liked Super Bowl XXXII.

A carp-droppin’ tradition. A relatively new tradition in Prairie du Chien happens on New Years’ Eve. In 2001, they started lowering a carp via crane to coincide with the ringing in of the new year. Similar to the apple in New York City or the peach in Georgia, residents count down the last minute or two of the year while the carp – a 30-pound female named “Lucky” – gets lowered via crane from about 110 feet high. Now called the “Droppin’ of the Carp”, it’s certainly one-of-a-kind.

Prairie du Chien contains five National Historic Landmarks and nine sites on the National Register of Historic Places. Wyalusing State Park lies just to the south of the Wisconsin River via the Great River Road.

Highway 27 ends at U.S. 18 in Prairie du Chien
Highway 27 comes to an end right before the bridge to Iowa, at U.S. 18/Highway 60 on the south edge of Prairie du Chien’s downtown.


North Terminus:
Can connect immediately to: U.S. Highway 2
Can connect nearby to: Highway 13, about 6 miles north

South Terminus:
Can connect immediately to: Highway 35
Can connect nearby to: U.S. Highway 18 & Highway 60, about 0.5 miles south