Madison to Deadwood via I-90 W
Take A Road Trip

Route Distance: 814 miles

Suggested Time: 7 days

Travel Time: 11 hours and 40 minutes

You’re about to embark on the quintessential American road trip. Your destination? Deadwood, the storied town that’ll make you think you’ve been teleported to the Old West where notorious outlaws roamed and the saloons they frequented still stand. Oh, there’s also a lot of fun to have along the way. 

So pack the wagon and round up the herd! From the Badger State to bison country, here’s your road map for the best family vacation ever. Don't forget to order your Vacation Guide before hitting the road to discover even more South Dakota adventures.

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Coach on Historic Main Street Deadwood
Madison, WI → La Crosse, WI (2 hours, 18 minutes)

Head west on I-90. (This trip is basically a straight shot down this interstate). After a little over two hours, stretch your legs in this town that borders Minnesota – and take in those vistas of the Mighty Mississippi. Hungry? Stop for lunch at Green Grass Café (great kids’ menu) or The Root Note (holy crepes!).

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La Crosse, WI → Sioux Falls, SD (4.5 hours)

Continue along I-90, skirting the southern edge of Minnesota, to your first overnight stop: Sioux Falls, South Dakota’s largest city and a hub of creative activity. 

Things to Do

There’s a ton of stuff to do here. Be sure to visit Falls Park (131 E Falls Park Dr.). Stroll along the SculptureWalk to the Arc of Dreams (300 N Cherapa Place). The kids will love the Butterfly House Museum & Aquarium (4320 Oxbow Road). For some thrills and spills, opt for go karts, mini golf and human foosball (!) at Thunder Road of Sioux Falls (201 N Kiwanis Ave.). 

Falls Park
Falls Park
Sioux Falls SculptureWalk
SculptureWalk
Arc of Dreams
Arc of Dreams
Where to Eat

Once you’ve worked up an appetite, head to Pizza Di Paolo (2300 S Minnesota Ave.) for a menu everyone will love. For breakfast, you’ll want to head to retro-inspired Phillips Avenue Diner (121 S Phillips Ave.) at least once – you have to see their milkshake menu to believe it. (It is totally okay to have milkshakes for breakfast.)

Places to Stay

For a real taste of local history and culture with a side of vintage charm, stay at Historic Victorian Inn (117 N Duluth Ave.), Hotel on Phillips (100 N Phillips Ave.) or in nearby Lennox at the Steever House Bed & Breakfast (46850 276th St.).

Sioux Falls, SD → Rapid City, SD (5 hours)

It’s on this stretch of I-90 where the most iconic South Dakota sights come into view. 

Things to Do

Your first stop on the way out is Mitchell, where you’ll find the World’s Only Corn Palace (604 N Main St.) and delicious popcorn balls! Next, get a family photo in at the Minuteman Missile National Historic Site (24545 Cottonwood Road, Philip). For jaw-dropping Badlands panoramas, stop at Big Badlands Overlook in Badlands National Park. And no road trip through South Dakota is complete without a stop at Wall Drug (510 Main St.) in Wall – spot the rare jackalope and grab some donuts on your way out of town.

Next, take a load off in Rapid City. It’s a great jumping-off point for attractions like Mount Rushmore and the South Dakota Air and Space Museum (2890 Davis Drive, Rapid City), not to mention the Black Hills. Stroll downtown Rapid City to see Art Alley as well as the statues of 44 U.S. presidents.

Badlands Overlook
Big Badlands Overlook
Wall Drug
Wall Drug
Where to Eat

Grab a bite at Sickies Garage Burgers & Brews (3313 E Mall Drive) – they have a ridiculously long sandwich menu. For imaginative dishes that source local ingredients, head to Tally’s Silver Spoon (530 6th St.).

Places to Stay

Rapid City has just the room to suit your style. Opt for an amenity-rich boutique experience at Summer Creek Inn & Spa (23204 Summer Creek Dr.), or go with a familiar brand like Comfort Suites

Rapid City, SD → Deadwood, SD (46 minutes)

Ready to step back in time? Mosey on down to Deadwood, where the Old West comes to life in its gamblin’ rooms and saloons, but don’t worry — this town is packed with all-ages fun. (Some of it is even educational!)

Tatanka: Story of the Bison, Deadwood
Things to Do

Get a closer look at 19th-century life in Deadwood at the Historic Adams House (22 Van Buren St.) and wander around downtown Deadwood, which looks almost exactly as it did in 1876. Next, see the gravesites of legendary Old West figures like Calamity Jane at Mount Moriah Cemetery (10 Mt. Moriah Dr.), and learn the history of South Dakota’s majestic herds of buffalo at Tatanka: Story of the Bison (100 Tatanka Dr.).

Where to Eat

On the floor above the Saloon #10 (657 Main St.) — also known as “the only museum in the world with a bar” — the Deadwood Social Club boasts an intriguing menu full of hearty Northern Italian dishes as well as a surprise or two. (Ever think you’d see Pad Thai on a menu in this town?) Also worthy of a visit is Hickok’s Hotel restaurant (685 Main St.).

Places to Stay

And of course, you’re going to want to make an immersive experience of it with a historic hotel. Try Bullock Hotel (633 Main St.), Deadwood’s first and oldest (and haunted, according to some!) hotel or Iron Horse Inn & Casino (27 Deadwood St.) in the heart of town.

SEE WHAT GREAT PLACES OTHERS DISCOVERED ON THEIR SOUTH DAKOTA ROAD TRIP