Kristi Schultz is the author of “Roadtrip Adventure: Discovering the National Parks of the Upper Midwest”, and the blog owner at https://www.roadtrippersrus.com
The Upper Midwest is a region in the northern United States and is largely a subset of the Midwest Region consisting (by most definitions) of the states of Minnesota, Wisconsin, Michigan, North & South Dakota, Illinois, and Iowa. There are a lot of people in the world who don’t even know these states exist, but they’re amazing places to visit!
The region has a lot to offer in our nation’s history and beauty. It is home to the Great Lakes, Great Plains, and the varied landscapes of the Missouri and Mississippi Rivers, including the Driftless Area.
Economically, it’s focused on industry and agriculture, and is also home to Chicago, the nation’s third largest city. Explorers Marquette & Joliet as well as Lewis & Clark came through here and interacted with the many Native American tribes that called it home.
There are over 20 National Parks, Monuments, and Historical Sites in the Upper Midwest, offering an epic roadtrip adventure over 16 days and covering over 3300 miles.
Given the climate in this area and the seasonal nature of these destinations, summer time is the best time for this roadtrip – between Memorial Day and Labor Day. May or September could be included, but many places won’t be open.
Here I’ll give you a day by day itinerary. You can adjust this based on how many days you have. I’ll point out a few places where you can skim off time if you have fewer days.
However, if you skip anything or really want to explore each region, you should plan a different trip to the area. There will be a lot of great stuff that you will need to drive by & bypass in order to fit everything in!
The starting (and ending) point for this roadtrip is Chicago. Chicago’s O’Hare Airport is International and a hub for every major US airline. This allows folks who live outside the area to easily fly in. The route will start by taking you through Northern Illinois, SW Wisconsin, and the NE corner of Iowa.
From there, you’ll cross along southern Minnesota into South Dakota and touch the NE corner of Wyoming. Heading up along the Eastern side of Montana, you’ll enter Northern North Dakota and head back into Northern Minnesota.
With the option to set foot on Canadian soil, you’ll follow the coast of Lake Superior, the largest of the five Great Lakes and head into Northern Wisconsin.
Traveling through Upper Peninsula Michigan, you’ll take the 5-mile-long Mackinac Bridge into Lower Michigan. Heading down the western side of Michigan, you’ll skim the NW corner of Indiana before re-entering Illinois and back to Chicago.
It’s worthy to note that it is quite a trek to drive through North & South Dakota, but the parks and sites to see on the other side are well worth the time it takes to get there. We’ll break up the travel time so that it won’t be quite so monotonous, but you won’t be able to help getting a little tired of the scenery, so don’t forget to bring along activities & music to pass the time!
National Parks, Monuments, and Historic Sites You Will Visit
NOTE: Click on the links for overview youtube videos.
- Chicago Portage National Historic Site
- Illinois &Michigan Canal National Heritage Area
- Effigy Mounds National Monument
- Pipestone National Monument
- Minuteman Missile National Historic Site
- Badlands National Park
- Mt Rushmore National Monument
- Wind Cave National Park
- Jewel Cave National Monument
- Devil’s Tower National Monument
- Theodore Roosevelt National Park
- Fort Union Trading Post National Historic Site
- Knife River Indian Villages National Historic Site
- Voyageurs National Park
- Grand Portage National Monument
- Isle Royale National Park
- Apostle Islands National Lakeshore
- Pictured Rocks National Lakeshore
- Father Marquette National Memorial
- Sleeping Bear Dunes National Lakeshore
- Indiana Dunes National Lakeshore
- Pullman National Monument
Before You Go
You will want to start out on a Saturday after Memorial Day and before Labor Day in order for the itinerary to work out with the times and days of operation & the suggested tours.
In order to go on all of the tours suggested on this itinerary, you’ll want to go online several months in advance and purchase tickets. Otherwise, you may not be able to go. Here are the suggested tours:
- I&M Canal Mules, Mansion & Mimosas Boat Tour
- Tour of the Launch Control Facility Delta-01
- Wind Cave Natural Entrance Tour
- Crazy Horse Memorial Trip of a Lifetime Tour
- Jewel Cave Scenic Tour
- Kettle Falls Boat Tour
- Apostle Islands Classic Grand Tour
- Isle Royale Boat Day Trip or Seaplane
- Pictured Rocks Spray Falls or Kayak tour
You’ll also want to purchase the following:
- iPass/EZPass to save money and time on the tollroads
- National Park Pass
- Minnesota State Park Pass
- Chicago CityPass if you’re spending more time there
You will be driving through some pretty remote areas with little or no services for 100’s of miles (really!). I recommend you also do the following prior to your trip:
- Get your vehicle serviced & ensure good tires and batteries
- Make sure you know how to change a tire, you have the tools & spare, and it’s not too hard to get to it.
- Make sure you know how to properly charge your battery and bring a trickle charger along
- Bring along extra window washer fluid
- Bring along an emergency kit
- Make sure you take advantage of suggested bathroom breaks
- Make sure to have extra water on hand
- Bring along some entertainment and brush up on your travel games
- Print or screenshot maps for the day
The Daily Itinerary
Day 0 – Arrive in Chicago (Friday)
- Take the train downtown and explore the Chicago Loop
- Eat dinner at:
- Stay near the airport:
Day 1 – Chicago to LaSalle, IL (Saturday)
The first day is spent exploring the Chicago Portage National Historic Site and the Illinois & Michigan Canal National Heritage Area. The site in Chicago is the only remnant left of the discovery and settlement of Chicago and marks the place where the portage was revealed to French explorers Pere Jacques Marquette and Louis Jolliet.
The portage represents the start of the 97 mile I&M Canal linking Lake Michigan to the Mississippi River waterways. This canal was critical to the rise of Chicago as the transportation hub of the nation and the 3rd largest city.
- Breakfast: Mary’s Morning Mixup – locally owned diner
- Chicago Portage National Historic Site – the Birthplace of Chicago
- Sculpture, trails, bicycle trail
- Drive to LaSalle, IL (82 miles, 1.5 hours), I-55 S & I-80 W
- Illinois & Michigan Canal National Heritage Area – Mules, Mansion & Mimosas Boat Tour
- Ride a Mule-drawn canal boat, lunch at Lock 16 Café, visit Hegeler Carus Mansion
- Starved Rock State Park for hiking & scenery
- Lover’s Leap Overlook Trail & French Canyon Trail
- Stay at Starved Rock Lodge
- Eat at: Haze Smokehouse – some of the state’s best BBQ, locally owned since 2015
Day 2 – LaSalle, IL to McGregor, IA (Sunday)
The Great River Road National Scenic Byway and Effigy Mounds National Monument marks today’s highlights. The Great River Road follows the course of the Mississippi River from northern Minnesota to the Gulf of Mexico. Today, you will experience the Iowa portion.
Effigy Mounds protect more than 200 prehistoric mounds from 20 American Indian tribes, some of them in the shape of animals. The site includes a visitors center and trails.
- Breakfast at the lodge
- Drive to Dubuque, IA (3 hours)
- Take exit 45 from I-80 W, taking IL-40 N to I-88 W, then US-30 W to US-67 N
- Follow the Great River Road along the Mississippi River
- After crossing the river in Fulton/Clinton, drive through Eagle Point Park for the views and use the restrooms
- In Dubuque, stretch your legs & ride the Fenelon Place Elevator – the world’s shortest, steepest scenic railway
- Drive to Effigy Mounds National Monument
- Take US-61 N out of Dubuque, 20 miles to Co Rd U to WI-35 N (Great River Road)
- Lunch at Pete’s Hamburger Stand in Prairie du Chien
- Take US-18 W across the river to Effigy Mounds
- Visit the Visitor’s Center & Hike the trails
- Pikes Peak State Park
- Hike Bridal Veil, Hickory Ridge, Weeping Rock Trails, see the views
- Explore the towns of McGregor and Marquette
- Dinner at: River View, McGregor
- Stay at: The Stauer House B&B or Cobblestone Inn & Suites
Day 3 – McGregor, IA to Sioux Falls, SD (Monday)
Today is a drive through southern Minnesota and the primary stop is Pipestone National Monument. The monument preserves the site where American Indians have quarried the red pipestone found here for generations. The site is considered sacred and the pipes carved from the pipestone are used for prayer. The traditions continue today and can be observed at the site.
- Breakfast at the B&B or Inn
- Drive to Austin, MN (2.25 hours) IA-76 N to IA-9 W to US-63 N to IA-56 W to I-90 W
- Take a break and visit the free SPAM Museum
- Have a SPAM burger for lunch at the SPAM food truck
- Drive to Pipestone National Monument (3 hours)
- Des Moines River Rest Stop (Jackson, MN) (1.5 hours in)
- Historical markers, flush toilets
- Prairie Passages Route Scenic overlook
- Pipestone National Monument – $7 entrance fee
- Visitor’s Center, cultural demonstrations, short trail
- Des Moines River Rest Stop (Jackson, MN) (1.5 hours in)
- Drive to Sioux Falls & stay overnight – 1 hour drive
- Falls Park to see the falls and historical markers
- Dinner: Minervas
- Stay Overnight
Day 4 –Sioux Falls, SD to Keystone, SD (Tuesday)
Today is a long drive through South Dakota and the highlights include Minuteman Missile National Historic Site, Badlands National Park, and Mount Rushmore at night. Minuteman Missile preserves two sites that were once part of a vast network of nuclear missile silos and underground control centers during the Cold War. Today, you can learn about and tour these facilities.
Badlands National Park is a dramatic display of rock formations, rugged canyons, towering spires, and vast grasslands. It contains one of the world’s richest fossil beds. The scenery is breathtaking and many scenic trails and overlooks are available. Make sure you bring plenty of water to this arid landscape.
Mount Rushmore will be more fully explored tomorrow, but the lighted display at night is worth a visit.
- Breakfast at Phillips Avenue Diner
- Drive to Akta Lakota Museum & Cultural Center, Chamberlain, SD (2.25 hours)
- Take a break, use the restroom, & visit the museum
- Ensure you have a lot of water to drink for rest of the day
- Drive to Minuteman Missile National Historic Site (2 hours) on I-90 W, exit 127
- Lunch at Murdo Drive-In
- 30 min Tour of the Launch Control Facility Delta-01 31 feet underground (advance reservations required)
- Drive through the Badlands National Park – hike trails, spend the afternoon
- Take I-90 East back to exit 131, SD-240 W
- Notch Trail, Door Trail, Saddle Pass Trail
- Drive to Keystone, SD (2.5 hours) SD-44 W to US-16 W
- Eat at: Jane’s Boardwalk Pizza or Himalayan Indian Cuisine in Keystone
- Stay Overnight: Rushmore Express Inn & Family Suites in Keystone
- Go see Mt Rushmore at night
Day 5 –Keystone, SD to Custer, SD (Wednesday)
The South Dakota Black Hills are a small mountain range and an area rich in culture, history, nature, scenery, and adventure. You can easily spend two weeks here and not experience it all. There is hiking, rock climbing, fishing, camping, backpacking, family activities, and more.
Our National Park highlights today include exploring Mount Rushmore National Memorial and Wind Cave National Park. Mount Rushmore has 60 foot sculptures of the faces of four US presidents, Washington, Jefferson, Theodore Roosevelt, and Lincoln, carved into the mountainside as a shrine to democracy. The park includes a visitor center and trails.
Wind Cave National Park is one of the longest and most complex caves in the world, home to boxwork, a unique formation rarely found anywhere else in the world. The park includes hiking trails and daily cave tours.
- Grab coffee at Grapes & Grinds
- Pack a picnic lunch to eat along the way today
- Take the morning & drive Needles Hwy (SD-87 S) through Custer State Park down to Wind Cave
- Stops at Mt Rushmore, Sylvan Lake, scenic outlooks (3+ hours)
- Wind Cave National Park (open until 4:30) 5 hour tours: 12:20, 1:40, 2:20, 3:40, and 4:20 – reserve in advance
- Eat dinner at Skogen Kitchen in Custer, SD
- Open 5pm-8pm
- Crazy Horse Memorial – laser show at 9:30p or 10p, visitor center open until 30 min later
- Stay at Chief Motel in Custer, SD
Day 6 –Custer, SD to Medora, ND (Thursday)
The three main sites today include Jewel Cave National Monument, Devil’s Tower, and Theodore Roosevelt National Park. Jewel Cave is currently the third longest cave in the world, with 192.99 miles of mapped passages and daily tours. Devil’s Tower National Monument is technically not in the Upper Midwest, but is a on the way to Theodore Roosevelt NP, and well worth the visit.
The tower is a geological feature protruding 867 feet from its base to its summit and with a circumference of 1 mile. It is considered sacred by native americans. The site includes a visitors center and trails around the base.
Theodore Roosevelt National Park has three units and includes Painted Canyon, prairie, a scenic loop, and hiking trails. Theodore Roosevelt hunted bison here and later established a residence and ranch that are now included in the park.
- Breakfast at Our Place in Custer
- Take US-16 W to Jewel Cave National Monument
- Scenic Tour at 10am – 1.5 hours
- Make reservations in advance
- Drive to Devil’s Tower (1.5 hours)
- US-16 W to US-85 N to WY-585 N to US-14 w to WY 24 E
- Spend an hour walking the trail around the tower
- Eat lunch at the Hitchin Post in Hulett, WY (WY 24 E)
- Drive to Medicine Rocks State Park (2 hours) WY-112 N, WY-323 N, MT-7 N
- $6 vehicle fee
- Spend 30 minutes (pit toilets with short trails)
- Drive to Painted Canyon Visitor Center (2 hours) MT-7 N to I-94 E
- Theodore Roosevelt National Park
- Prairie dog towns & Wind Canyon Trail before/after dinner
- Eat at Roughrider Bar and Steakhouse in Belfield, ND
- Stay at Rough Riders Hotel in Medora, ND
Day 7 Medora, ND to Killdeer ND (Friday)
235 miles (plus 14 mile scenic loop)
Today includes continuing to explore Theodore Roosevelt National Park as well as the Fort Union Trading Post National Historic Site. The site includes a partially reconstructed fort and trading post on the North Dakota & Montana border. It marks the most important fur trade post on the Upper Missouri River and includes cultural exhibits & a visitor center.
- Breakfast at Theodore’s Dining Room
- Spend the morning driving the Scenic loop drive In Theodore Roosevelt NP
- Petrified Forest Trail, overlooks
- Drive to Fort Union Trading Post (2.25 hours)
- Lunch at Backyard in Beach, ND (last chance)
- Fort Union Trading Post
- Visitor Center, cultural exhibits, find the wagon ruts of the Santa Fe Trail
- Drive to North Unit Visitor Center (1 hour – scenic overlook)
- Dinner at Mic’s Tavern Zap, ND
- Stay AmericInn Lodge & Suites Beulah, ND (1.5 hours away)
Day 8 Beulah, ND to Blackduck, MN (Saturday)
Today is largely spent driving across North Dakota and into Minnesota. It includes a stop at the Knife River Indian Villages National Historical Site along the Missouri River. The site was a major trade center and fur market place and commemorates Northern Plains native americans. It includes a museum, reconstructed village, and trails.
- Get up early & have breakfast at Sue’s Café in Hazen, ND 10-15 minutes down ND-200 E
- Drive to Knife River Indian Villages (1.25 hours)
- Knife River Indian Villages National Historical Site
- Museum, Earthlodge, Village Trail, North Forest Trail
- Lunch at Café 77 in Washburn, ND
- Lewis and Clark Interpretive Center in Washburn if time (long drive ahead)
- Drive to Hiway Drive In, Carrington, ND (2.25 hours) & eat if hungry
- Drive to Crookston, MN (2.5 hours) eat at Snow Sled Inn if hungry
- Stay at Drake Motel in Blackduck, MN (another 2 hours)
Day 9 Blackduck, MN to Orr, MN (Sun)
Voyageurs National Park is made up of forests, waterways, lakes, and islands. It borders Canada. Hiking, canoeing, and rustic camping are popular and some sights can only be seen by boat. It includes visitors centers, a 20th century hotel, and Ellsworth Rock Gardens. If you’re lucky, you may even get to experience the Northern Lights!
- Leave early today – 6:30am
- Have breakfast at Shining Light Cafe in Northome – 20 min down the road
- Drive to Kabetogama Visitors Center (1.75 hours) Voyageurs National Park
- Boat tours to Kettle Falls (6 hours) – leaves at 10am, be there by 9:30a – includes lunch
- Blind Ash Bay Trail (3.5 mile hike) from Kabetogama Lake Overlook (25 min drive)
- Dinner at Sandy Point Lodge (10606 Gamma Road)
- Stay in Frontier Resort near Orr, MN
Day 10 Orr, MN to Grand Portage, MN to Beaver Bay, MN (Monday)
NOTE: If you’re short on time, you can skip the North Shore & Grand Portage and save a day. Drive from Orr, MN to Bayfield, WI and carry on.
Today you will drive through Minnesota’s Iron Range and up the North Shore of Lake Superior. Grand Portage National Monument commemorates the partnership of the Ojibwe Nation & the North West Company trading post. It consists of historical buildings, Visitors Center, and trails. Further north, there is a beautiful waterfall. The highest in Minnesota.
- Have breakfast at the resort
- Drive to Oldtown-Finntown Overlook (1.3 hours) to see mining operations (US-53 S)
- US Hockey Hall of Fame – Eveleth
- Drive to Tettegouche State Park (1.5 hours)
- MN-37 E to Co 97 to Heritage Trail to Co 4 to Co 16/15/11
- Lunch at North Woods Family Grille, Silver Bay, MN
- Drive to Grand Portage National Monument (2-4 hours) (MN-61 N)
- Caribou Falls State Wayside
- Father Baraga’s Cross Historical Marker
- Temperance River State Park, Cascade River State Park, Judge CR Magney State Park (Devil’s Kettle waterfall)
- Grand Portage State Park (Minnesota’s highest waterfall)
- NOTE: There is a shorter boat ride to Isle Royale from here, but it does not operate on Tuesdays.
- Drive down to Beaver Bay, MN that evening (US-61 S)
- Eat dinner at My Sister’s Place, Grand Marais, MN
- Stay at Cove Point Lodge, Beaver Bay, MN
Day 11 – Beaver Bay, MN to Bayfield, WI (Tuesday)
Today’s focal point is the Apostle Islands National Lakeshore. It is made up of 21 islands and 12 miles of mainland coast. It is best experienced by boat to get a good view of the sea caves and access to the islands.
- Eat breakfast at the lodge & head out early
- Drive to Duluth, MN (2-3 hours)
- Split Rock Lighthouse SP
- Gooseberry Falls SP
- Aerial Lift Bridge, Duluth
- Early Lunch at Anchor Bar & Grill, Superior, WI (Featured on Triple D)
- Drive to Bayfield, WI (1.45 hours) (leave by 11:30)
- Apostle Islands National Lakeshore – Classic Grand Tour at 2pm (3.5 hour tour)
- Dinner at Maggie’s
- Stay at Bayfield Inn or Old Rittenhouse Inn (B&B)
Day 12 – Bayfield, WI to Copper Harbor, MI (Wednesday)
The next two days can be skipped if you don’t have time (although I would recommend coming back!) You can drive from Bayfield, WI to Munising, MI (247 miles) and then skip to Day 14 (Pictured Rocks). If you have time, carry on!
The Keweenaw Peninsula is the area we are exploring today. It includes the Keweenaw National Historical Park made up of copper mines, museums, and surrounding communities. It also includes Porcupine Mountains State Park, one of the few remaining wilderness areas in the Midwest. The peninsula is another place you may want to come back to!
- Breakfast at Café Coco – Artisan Bakery & Good Eats in Washburn, WI
- Drive to Porcupine Mountains State Park (WI-13 S to US-2 E to Co-519 N)
- Hike Presque Isle River Waterfalls Loop
- Lake of the Clouds scenic overlook
- Lunch at Lynns North Country Café
- Drive to Keweenaw National Historical Park (MI-64 to MI-38 to MI-26 to US-41
- Museums, Central Mine, Calumet, Mine tours
- Drive to Copper Harbor, MI
Day 13 – Day trip to Isle Royale (Thursday)
Isle Royale is a rugged, isolated island in Lake Superior with no roads and one hotel. It offers hiking, backpacking, canoeing/kayaking, and scuba diving. It is also host to moose and wolves. You can only get here by boat or seaplane. Many people take multi-day backpacking adventures here.
- Pack a picnic breakfast for the 3 hour boatride
- Take the Day Trip Boat to Isle Royale National Park – Rock Harbor (8am departure) or splurge for a seaplane ride!
- Lunch at Rock Harbor Lodge
- Hike part of Scoville Point Loop
- Dinner at Tamarack Inn Restaurant back in Copper Harbor
- Stay at Bella Vista Motel again in Copper Harbor
Day 14 – Copper Harbor, MI to Munsing, MI (Friday)
Pictured Rocks National Lakeshore is the main event for today. It consists of 60 miles of Lake Superior shoreline and is known for the multicolored cliffs and unusual sandstone formations. The beauty of this park is best seen by boat or kayak. Hiking trails are also available.
- Drive to Van Riper State Park (2.25 hours) (US-41 E)
- Stretch your legs, use the restroom
- Drive to Munsing, MI (1.5 hours) (US-41 E to Co-480 to MI-28 E)
- Lunch at Johnny Dog or The Fish Basket
- Boat ride to Pictured Rocks National Lakeshore (2pm 3 hour Spray Falls tour or 3pm kayak tour (5-6 hours total))
- Stay at Voyageurs Motel or Superior Hotel (B&B) in Grand Marais, MI
Day 15 Grand Marais MI to Frankfort, MI
Today’s focus is Father Marquette National Memorial and the Sleeping Bear Dunes National Lakeshore. At the memorial, you can learn more about Father Jacques Marquette, one of the earliest European explorers of Canada and Northern US. There are also great views of the Mackinac Bridge.
Sleeping Bear Dunes consists of 65 miles of Lake Michigan shoreline, numerous lakes & streams, immense sand dunes, 400 foot bluffs, forests, meadows, and wetlands.
- Drive to Father Marquette National Memorial (2 hours) (M-77 S, US-2 E)
- Museum, walking paths, view of the bridge, overlook
- Spend 30 minutes (10-10:30a)
- Lunch at Traverse City (2 hour drive) (I-75 S to M-32 to US-131 S to M-72 W to US-31 S)
- The Filling Station Microbrewery or Spanglish
- Drive to Sleeping Bear Dunes (40 min) (arrive 2:30p)
- Pierce Stocking Scenic Drive, Empire Bluff Trail, Pyramid Point Loop, Sleeping Bear Point Trail
- Drive to Frankfort, MI (M-22 S)
- Dinner at Coho Cafe
- Stay at Hotel Frankfort in Frankfort, MI
Day 16 Frankfort, MI to Chicago, IL
The highlights of today include Indiana Dunes National Lakeshore and the Pullman National Monument. The Indiana Dunes preserves 15 miles of the southern shore of Lake Michigan and consists of trails through sand dunes, wetlands, prairies, rivers, and forests.
The Pullman National Monument is one of the newer monuments meant to preserve Pullman, the first model, planned industrial community in the US. It consists of a the Pullman factory, Hotel Florence , and Pullman Porter Museum.
- Breakfast at Crescent Bakery and Cafe
- Drive to Indiana Dunes (4.5 hours) (US-31 S)
- Restroom break & stretch legs at Chinook Pier Park (2.25 hours in) Grand Haven
- Indiana Dunes National Lakeshore (US-31 S, I-196 S, I-94 W, exit 34B)
- Little Calumet River Trail Loop (3 hours to go 4 miles)
- Drive to Chicago (1 hour) (I-94 W)
- Pullman National Monument (exit 66B)
- Visitor’s center, walking tour of the neighborhood
Day 17 – RELAX!!!
You did it!! Come again and explore the area in more depth. The Upper Midwest has a lot to offer.
Visit roadtrippersrus.com for upcoming posts that will go into more detail for this roadtrip and others!