Best Rides from Chicago or Milwaukee to Sturgis

Distance: 985 miles from Chicago; 893 miles from Milwaukee
Time (Before Stops): 15 hours from Chicago; 13 hours, 25 minutes from Milwaukee

See route map

Point your bike north along the shores of Lake Michigan to the headquarters of Harley-Davidson before steering west toward fun and gaming in the Dells, a cathedral of canned meat in Minnesota and roadside attractions galore along the entire road to Sturgis.

Milwaukee, WI

• Harley-Davidson Museum: Swing through the Motorcycle City to tour the birthplace of Harley-Davidson, where you can explore one-of-a-kind dining, shopping and events celebrating all things H-D.

Wisconsin Dells, WI

• How long you spend in the Dells is up to you, but there are enough activities to keep you busy for a week, from car racing and zipline tours to axe throwing and gaming.

Sparta, WI

• FAST Fiberglass Mold Graveyard: Just north of I-90, see giant molds of roadside attractions past from the FAST Corporation, foremost makers of kitschy promotional statues. 

La Crosse, WI

• World’s Largest Six-Pack: Several brewers have occupied this historic building, including Old Style, La Crosse and now City Brewing. Breathe in the aroma of cooking grains as you grab a pic in front of the beer tanks-turned six-pack. La Crosse is an ideal stopping point for the night, with plenty of hotels lining the Mississippi River.

Austin, MN

• SPAM Museum: You don't have to like SPAM to enjoy this museum that explores the canned meat's quirky (and distinctly Midwestern) history. 

Albert Lea, MN

• Bergdale Harley-Davidson: Should you need something for your bike, this H-D dealership has got you covered. 

Blue Earth, MN

• Jolly Green Giant Statue and Museum: Make a quick stop to see this 55-foot version of everyone’s favorite frozen vegetable spokesman. The Green Giant company was founded in nearby Minneapolis, but the genius behind the statue was a local radio station owner who hosted a show interviewing travelers en route to the Black Hills and Yellowstone.

Jackson, MN

• Fort Belmont: This recreation of a pioneer fort includes a prairie sod house, blacksmith shop, replica 1860s log cabin and stockade, and other buildings from the frontier era.

Brandon, SD

• Big Sioux State Recreation Area: Just before Sioux Falls, pause for a stretch at this scenic park whose trails wind along the Big Sioux River.

Sioux Falls, SD

• Bread & Circus Kitchen: Be sure to work up a proper appetite for a meal at this downtown restaurant; the signature Vietnamese Fried Chicken sandwich was devoured by the Mayor of Flavortown himself on “Diners, Drive-Ins & Dives.”
• Severance Brewing Co.: A walk around the block will bring you to crisp ales and corn lagers at this brewery that helped spark Sioux Falls' craft beer movement.
• Falls Park: A trip to Sioux Falls isn't complete without visiting this sprawling park, home to the city’s namesake waterfalls.
• Flyboy Donuts: If you still have room in your belly, head to this popular bakeshop serving from-scratch donuts in many decadent flavors.
• J&L Harley-Davidson: Your H-D HQ in the Sioux Falls area.

Mitchell, SD

• Palace City Pre-Sturgis Party (Aug. 1, 2024): Time your trip for a stop at this only-in-SoDak throwdown, which unfolds at the World’s Only Corn Palace. Enjoy food from a variety of vendors, live music, stunt shows and a beverage garden.

Oacoma & Chamberlain, SD

• Al’s Oasis: This pit stop is an all-American classic. Grab a five-cent coffee and a slice of homemade pie before wandering to check out the iconic buffalo statue and other kitschy sights.
• Dignity: Of Earth & Sky: Take in the majesty of this 50-foot-tall statue of a Native woman that honors South Dakota’s Lakota, Dakota and Nakota heritage. Next door is a visitor center that explores Lewis & Clark’s expedition of the Missouri River.

Philip, SD

• Minuteman Missile National Historic Site: Just before Wall and the Badlands, brake for Cold War history at this former missile silo-turned museum.

Wall, SD

• Wall Drug Store: The biggest roadside attraction of them all, Wall Drug has been serving free ice water — and much more — since 1931. Might as well stop into Badlands Harley-Davidson while you're there.
• Badlands National Park: Journey through one of the world’s richest fossil beds at this otherworldly park, where bison wander among jagged buttes, wide prairies and twisting spires.

Rapid City, SD

• Museum of Geology: Learn even more about South Dakota’s prehistoric history at this museum, located on the campus of the South Dakota School of Mines & Technology.
• Bear Country USA: See more than 20 species of bears and other North American mammals at this 250-acre drive-through wildlife park.

Distance: 953 miles from Chicago; 887 miles from Milwaukee
Time (Before Stops): 19 hours from Chicago; 17 hours from Milwaukee

See route map

In the early days of America’s highway system, Highway 14 was promoted as the fastest and most direct route from Chicago to Yellowstone National Park via South Dakota’s Black Hills. Dubbed the “Black and Yellow Trail,” the highway offers an interstate-free alternative for getting to Sturgis — perfect for those who want to bypass the bigger cities and take things a little slower. It’ll add about four hours to your travel time, but you know what they say about the journey being the destination…

Woodstock, IL

• “Groundhog Day” filming locations: Small-town Woodstock doubled for Punxsutawney, PA, in the 1993 Bill Murray classic. Snap a selfie in front of the colorful mural in an alley — a key filming location — then head to the Cherry Tree Inn B&B to see where Phil wakes up on Groundhog Day every morning. There are plenty of quaint restaurants around town.

Madison, WI

• Wisconsin State Capitol Building: This grand old building is open daily for guided tours. Keep your eyes peeled for Old Abe, a taxidermied bald eagle that has watched over the Wisconsin State Assembly chambers since 1881.
• The Old Fashioned: Get a taste of Wisconsin at this retro restaurant serving The Badger State’s most famous foods and drinks, from cheese curds and walleye to 50 Wisconsin beers on tap.
• Vitense Golfland: A Madison icon, Vitense features a 9-hole golf course, driving range, batting cages and an epic mini-golf course named the best in the nation by Golf.com. 

Middleton, WI

• National Mustard Museum: More than 5,000 mustards from around the world are displayed at this fun museum just west of Madison. Bonus: The first Saturday in August is National Mustard Day, which just might coincide with your trip.

Spring Green, WI

• House On the Rock: You could spend an entire day at this wondrous attraction — and if you want to, there’s an on-site resort! Tour the 1945 home, an architectural delight packed to the brim with curious objects and exhibits. A slightly more high-brow home, Frank Lloyd Wright's Taliesin, is 10 minutes away.

Winona, MN

• Remlinger Collector Car Museum: Browse a mint collection of vintage muscle cars, drag-race cars, neon automotive signage and more.
• Boat House: Grab a burger, steak or fried walleye plate with a view of the Mighty Mississippi at this riverfront restaurant.
• Bloedow Bakery: Some say this is the best bakery in Minnesota; others claim it makes the best donuts in the country. Decide for yourself by sampling the famous maple long johns.

Rochester, MN

• Hollandberry Pannekoeken: If “pannekoeken” sounds a little like “pancake,” that’s because it’s a type of souffled pancake that hails from the Netherlands. Try this Dutch treat at Hollandberry, which has been baking up pannekoeken since 1986.
• Corn Water Tower: A perfect symbol of the Midwest, this 151-foot-tall tower has stood watch over Highway 14 since 1931. 

New Ulm, MN

• Hermann Heights Monument: This striking statue is a tribute to New Ulm’s German heritage. In fact, New Ulm has been called “the most German town in the United States.”
• August Schell Brewing: Take a tour of Minnesota's oldest brewery, founded in 1860, for just $10, and be sure to make a pit stop in the Bierhalle.

Brookings, SD

• South Dakota Agricultural Heritage Museum: Part of South Dakota State University, this museum focuses on the history, science and culture of farming in SoDak.
• McCrory Gardens: Also on the SDSU campus, take a stroll around this 70-acre oasis that’s home to an arboretum and formal display gardens. 
• Nick’s Hamburger Shop: A Brookings tradition since 1929, Nick’s sells juicy burgers that you may want to buy by the bagful (just to be safe).

De Smet, SD

• Laura Ingalls Wilder Historic Homes: History buffs and fans of “Little House on the Prairie” should not miss a stop in De Smet, the town where author Laura Ingalls Wilder spent her formative years.

Huron, SD

• World’s Largest Pheasant: This fiberglass and steel sculpture, which measures 40 feet from beak to tail, pays homage to South Dakota's world-class pheasant hunting.

Pierre, SD

• JD's Lounge: This hidden gem bar & restaurant is the perfect spot to cool down with some ice cold refreshment on the way to Sturgis.
• South Dakota National Guard Museum: Featuring military memorabilia, equipment and other relics from 1861 through today, this museum honors the heritage of the South Dakota Army and Air National Guard.

From Pierre, you have two options: Follow Highway 14 until it ends at Interstate 90, traveling through Midland, Wall, Badlands National Park and Rapid City before entering Sturgis from the south, or pick up Highway 34 to scoot through the plains and enter Sturgis from the north. If you’re looking to get to Sturgis faster, the northern route will shave about 15 minutes off your ride. If you want to see a few more sights and don’t mind getting into Sturgis a little later, opt for the southern route.