5 of the Best Upper Midwest Road Trips

December 23, 2020   14 Comments »

5 of the Best Upper Midwest Road Trips

July 10, 2018 14 Comments »

In an effort to bring you some new voices on Ottsworld, here is a guest post from blogger and road trip expert Kristi. She not only writes about road trips she’s taken (and she’s taken a lot!), she’ll also help you plan yours down to every detail! I was excited to have her write about Midwest road trips since it’s a region near and dear to my heart and often gets overlooked! All opinions and experiences expressed here are hers. –Sherry

I am a solo mom of three grown children and have lived in Minnesota or Wisconsin my entire life. I love road trips and discovering the beauty and wonders all around us, especially areas off the beaten path. I’ve traveled all around the wondrous United States and Canada, but I’ve spent many summers (and winters!) exploring an area less traveled known as ‘The Upper Midwest’.

The Upper Midwest is home to some of the most beautiful and scenic areas of the United States. Made up the states of Minnesota, Wisconsin, Michigan, Iowa, North & South Dakota, and Illinois, it is often overlooked by many travelers, leading to some of the most peaceful Midwest road trips you can find.

The region is diverse in its landscape and has some of the most unique geological features in the world. It includes many of the Great Lakes, the Great Plains, as well as the Missouri and Mississippi River. Steeped in history and culture, picking just five ‘best road trips’ is difficult indeed! Curious? Read on!

Table of Contents
Minnesota – North Shore
Where to stop on the North Shore
Wisconsin – Door County Scenic Byway
Where to stop in Door County
Iowa – Loess Hills Scenic Byway
Where to stop on Loess Hills Scenic Byway
Upper Peninsula Michigan – Keweenaw Peninsula
Where to stop in the UP
Great River Road Upper Midwest Roadtrip
Where to stop on the Great River Road
Don’t leave without this road trip gear

5 Best Midwest Road Trips

Minnesota – The North Shore

North Shore Minnesota road trip plan
Grand Portage Waterfall

Minnesota, known for its lakes, the Twin Cities of Minneapolis and Saint Paul, and the birthplace of the Mississippi River, is where we’ll start this Midwest road trip. Minnesota’s North Shore, which starts in Duluth and follows the Lake Superior coastline to the border of Canada, is designated as an “All-American Road”.

The North Shore offers rock and sandy beaches of the ever-changing and unpredictable Lake Superior, the largest of the Great Lakes, providing opportunities for kayaking, boating, and fishing. It also includes vast woodlands with hiking & biking trails, rivers and waterfalls, camping, wildflowers, wildlife, historical sites, and quaint communities.

Where to Stop on the North Shore

There are many places along the North Shore where you can spend time and explore for a week or more. This post just highlights just a few of the ‘must-see’ destinations:

  • Mile 0 – Canal Park, Duluth
  • Mile 30 – enjoy homemade pies from the iconic Betty’s Pies
  • Mile 40 – get up close and personal with the amazing falls at Gooseberry Falls State Park
  • Mile 91 – visit Lutsen Resort, with alpine skiing & snowboarding (largest in the Midwest), hiking, fishing, kayaking, and one of the best agate beaches on Lake Superior!
  • Mile 110 – Stop and eat some of the best fresh lake trout and whitefish at Dockside Fish Market. This family run business is near the base of the Gunflint Trail. With 55 miles of remote wilderness, where you may even spot a moose, it is a worthy side trip on your adventure.
  • Mile 124 – take the mile-long hike and 200 steps to visit the infamous Devil’s Kettle Falls, featuring half a river that disappears into the underground. The mystery of what happens to the river has supposedly been ‘solved’, but it’s still a unique phenomenon to witness.
  • Mile 150 – view Minnesota’s highest waterfall in Grand Portage State Park right at the Canadian border. The falls required a nine-mile portage from the river to Lake Superior named “Grand Portage”.
grand portage waterfall minnesota usa

Renting a Car

I have consistently found the best rental car prices on RentalCars.com (international and at home) and use them when I have to rent a car. They work with all of the major car companies; check out their prices and see what you think. They also offer free reservations and cancellations which I love as my plans often change!

Wisconsin – Door County Coastal Byway

Door county coastal byway midwest road trips
Sunset Over Green Bay from Old Post Office Restaurant, Ephraim WI

Wisconsin is known for its cheese, beer, forests and lakes, Harley-Davidson, The Fonz from Happy Days, The Ringling Brothers, and Frank Lloyd Wright and is next on our list. The Door County Peninsula has 300 miles of shoreline where you can watch the sunrise and the sunset over the water without leaving the county!

Door County is home to cherry orchards, art galleries, wineries, 5 state parks, 11 historic lighthouses, and 19 quaint communities. Taking a Midwest road trip to experience this county should be on your bucket list!

Where to Stop on Door County Coastal Byway

A vacation here can easily last a week or two – we will touch on some ‘must do’ highlights! Going clockwise, Hwy 42 to Hwy 57:

  • Mile 0 – start in Sturgeon Bay, a historic town with a strategic shipping corridor and known for its shipbuilding, music, and diverse food scene. It also has some of the best bass fishing in the world, so book a charter at Hooked Up Sport Fishing Charters for a great time!
  • Mile 26.2 – visit Peninsula State Park. Peninsula State Park is 3,776-acres of wooded trails, campsites, historical landmarks, and even a golfcourse! It includes miles of bicycle and hiking trails, high bluffs and sandy beaches with 8 miles of shoreline.
  • Mile 30.5 – experience a Fish Boil at Old Post Office Restaurant in Ephraim, an entertaining event featuring fresh caught fish, potatoes onions, and a huge cauldron over an open fire. As the oil from the fish rises to the top, kerosene is added to the flames causing the “boil over” to signal the food is done!
  • Mile 34.3 – check out the goats on the roof of Al Johnson’s, and then go inside to enjoy lingonberries and Swedish pancakes!
  • Mile 44.7 – enjoy the best cherry pie in the county at Bea’s Ho-Made Products. Door County was once the largest producer of cherries in the world and cherries remain an important part of the Door County experience.
  • Mile 46 – hop on the ferry to Washington Island and ride a bicycle around a 15 mile loop to experience the largest of 30 islands in Door County
  • Mile 69 – walk across a causeway to go up the Cana Island Lighthouse and get a birds eye view. You can visit all 10 of Door County lighthouses.
  • Mile 78 – stop at Cave Point County Park and watch (or participate!) swimmers jump off limestone shelves into the cool waters of Lake Michigan. Take the trail to discover a rocky beach filled with stacks of rocks from visitors past.
sunset sunrise reflection water

Iowa – Loess Hills Scenic Byway

Midwest road trips Loess Scenic Byway
Loess Scenic Byway

Iowa is known for its rolling plains and cornfields. Rich in tradition and agriculture, its cities serve as significant manufacturing and technology hubs. Often mistaken as being flat, Iowa is generally rolling, including steep hills and valleys in the driftless region of the state.

The Loess Hills Scenic Byway along western Iowa is a National Scenic Byway following a unique land formation made up of windblown soil from the ice age 15 miles wide and about 200 miles long from Sioux City, IA to St Joseph, MO. Only China has higher loess hills than Iowa.

With over 220 miles and many excursions and connections, there is much this area has to offer for a road trip. Remember what you’re appreciating here, and you won’t be disappointed.

Where to Stop on the Loess Scenic Byway

We will focus on just a few highlights here starting from the north in Akron, IA and taking Hwy 12 South:

  • Mile 23 – stop and visit the Dorothy Pecaut Nature Center, an interactive museum with indoor and outdoor exhibits and trails. They also have live birds of prey.
  • Mile 30 – experience the Lewis & Clark Interpretive Center, a 20,000 square foot cultural complex, commemorating the Lewis & Clark expedition that followed the Missouri River
  • Mile 100 – Murray Hill Scenic Overlook is a must-see stop and offers a panoramic view of the Missouri River Valley. There’s a parking lot and a steep climb to the overlook.
  • Mile 116 – don’t miss the Loess Hills Lavender Farm, enjoy the smells and sample the many products.
  • Mile 126 – step back in time and enjoy a milkshake at Penny’s Diner with decent food and excellent service!
  • Mile 185 – you’ll have to try Yeya’s Scratch Kitchen for great made from scratch comfort food and tex-mex! Locally owned and operated, you can’t go wrong here.
  • Mile 205 – get out and hike the trails at Waubonsie State Park. Named for a chief of the Potawatomi tribe. Enjoy the 7 miles of foot trails wind along ridges and down into gorges and valleys.
paved road countryside sunset sunrise

Upper Peninsula Michigan – Keweenaw Peninsula

Midwest road trips Michigan
Copper Harbor

For this post, we’re going to explore Upper Peninsula Michigan, separated from lower Michigan by Lake Michigan, the Straits of Mackinac, and Lake Huron. The UP is known for its wilderness, mining history, and lumber.

The Keweenaw Peninsula is the northern most part and is known as ‘Copper Country’. It is a road less traveled, with a lot to offer nature & history buffs.

Where to Stop on the Upper Peninsula

You can easily spend a week-long vacation here, but we will only focus on some highlights starting in Ontonagon and heading north.

  • Mile 0 – start with a hearty, homestyle breakfast at Lynn’s North Country Café in Ontonagon. Simple food with excellent service that makes you feel you’re right at home.
  • Mile 63 – Stop at Keweenaw National Historical Park Visitors Center and get your map of the area. The park is made up of many sites, tours, and museums. Make sure you tour a mine or two, visit the many museums, and explore some hiking trails.
  • Mile 63 – Eat like a local and order some of the best pasties at Toni’s Country Kitchen across the Hwy in Laurium. Pasties are meat & veggie filled pastries that are hand-held or served with gravy. It’s a UP tradition!
  • Mile 69 – don’t miss the Wood’n Spoon where you can get wild Thimbleberry Jam. Thimbleberries are like raspberries and blackberries, but are unique to UP Michigan.
  • Mile 81 – stroll the historical community of Central Mine, the site of one of Keweenaw’s most successful mines. The visitor center and gardens are a must see on your visit
  • Mile 99 – Fort Wilkins Historic State Park is at the northern most point and well worth your visit. The restored 1844 army military outpost is amazing, and the trails and lighthouse give you great views of Lake Superior.
  • Mile 97 – head back to Copper Harbor and take a 3-hour boatride to Isle Royale National Park, a rugged, isolated island with no roads and one hotel. Hike or kayak to explore the island or take a multi-day backpacking adventure!
rocky coastline copper harbor michigan

Great River Road – Upper Midwest Road Trip

Midwest road trips
Great River Bluffs State Park – Mississippi River Valley

The Great River Road National Scenic Byway  follows the course of America’s most iconic river, The Mississippi River, from Minnesota to the Gulf of Mexico in Louisiana. Established in 1938, the byway is a network of roadways well marked by road signs with a riverboat pilot’s wheel designating which roads are part of the official route.

The Great River Road is America’s oldest and longest National Scenic Byway. With over 3,000 miles, it can take 36 hours to drive it from beginning to end without stopping.

Where to Stop on the Great River Road

For this post, we will cover some ‘must see’ highlights in Iowa, Wisconsin, and Minnesota. Starting where it starts – Minnesota.

  • Mile 0 – walk across the headwaters of the Mississippi River and hike the trails at Itasca State Park. The Wilderness Drive Loop and Mary Gibbs Headwaters Center are not to be missed.
  • Mile 273 – hike the trails and see the house where Charles Lindbergh grew up at Charles Lindbergh State Park, right on the Mississippi River.
  • Mile 377 – Get up early for Al’s Breakfast for the best breakfast in Minneapolis in a diner crammed into a former alleyway. Featured on Diners, Drive-Ins, and Dives.
  • Mile 547 – take the short hike to the overlook and be treated to a panoramic view of the Mississippi River at Great River Bluffs State Park.
  • Continue crossing over to Wisconsin at La Crescent, MN and into La Crosse.
  • Mile 624 – enjoy a hamburger or two from Pete’s Hamburger Stand in Prairie du Chien. Serving up their unique style since 1908. While in town, also check out Stark’s Sport Shop – an icon to the area featuring taxidermy, hunting, fishing, and liquor – all in one store.
  • Mile 673 – tour the Potosi Brewing Company and sample its quality craft beers. Founded in 1852 and home to the National Brewery Museum, it’s a must-see spot in Wisconsin.
  • Mile 695 – Crossing over into Dubuque, IA, stretch your legs & ride the Fenelon Place Elevator – the world’s shortest, steepest scenic railway
  • Mile 792 – refresh yourself with a sundae or old-fashioned soda at Lagomarcino’s Confectionery in Davenport – an authentic soda fountain with homemade ice cream.
river landscape autumn fall trees color

Check out one of my favorite Midwest Road Trips

One of my favorite and unique road trips I’ve taken in the Midwest is in North Dakota along the Enchanted Highway to see the world’s largest metal sculptures! Seven massive sculptures placed out in pastures of rolling hills in the middle of nowhere – don’t miss it!

Don’t Leave Without this Road Trip Gear

Dramamine Tablets Less Drowsy Formula
$17.49 ($0.73 / Count)
Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
03/24/2024 11:47 am GMT
VICSEED Car Phone Mount
Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
03/06/2024 05:32 pm GMT
HOKENA LED Road Flares Emergency Lights

Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
05/08/2024 09:02 pm GMT
AVID POWER Tire Inflator Air Compressor

12V DC / 110V AC Dual Power Tire Pump with Inflation and Deflation Modes, Dual Powerful Motors, Digital Pressure Gauge

Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
03/07/2024 01:32 am GMT
Heavy Duty Booster Cables

Energizer 6 Gauge Jumper Battery Cables 16 Ft Booster Jump Start - Heavy Duty Booster Cables, UL Listed

Buy Now
03/07/2024 12:32 am GMT
Super Bright LED Tactical Torch

LE CREE LED Flashlight, Small and Super Bright LED Tactical Torch, Handheld Flash Light, Zoomable, Water Resistant, Adjustable Brightness for Camping, Running, AAA Batteries Included

Buy Now
03/07/2024 07:47 pm GMT
300W Power Inverter DC 12V to 110V AC

BESTEK 300W Power Inverter DC 12V to 110V AC Car Inverter with 4.2A Dual USB Car Adapter

Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
03/07/2024 09:32 am GMT
Shade Sox Universal Car Sun Shade

Shade Sox Universal Car Side Window Baby Sun Shade (2pc) | Protects Baby and Kids from the Sun| Fits All (99%) Cars Most SUV's | Travel ebook included!

Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
03/06/2024 11:32 pm GMT
ComfiLife Gel Enhanced Seat Cushion

ComfiLife Gel Enhanced Seat Cushion - Non-Slip Orthopedic Gel & Memory Foam Coccyx Cushion for Tailbone Pain - Office Chair Car Seat Cushion - Sciatica & Back Pain Relief

Buy Now
03/07/2024 01:17 am GMT
OtterBox Venture Cooler, Hudson, 45 Quart

Use an optional Dry storage tray or separator (both sold separately) to organize the interior however you like: keep Dry or soft items separate and create custom compartments

Buy Now
I earn a commission if you click this link and make a purchase, at no additional cost to you.
My top pick
VIM & VIGR Compression Socks & Sleeves

Compression socks are great for faster muscle recovery and to fight blood clots on long flights or long road trips.

PLUS - use discount code OTT15 for 15% off orders!

Shop Now
Contigo AUTOSEAL Water Bottle, 24oz, Spirulina

Great for travel - at 24oz, it's small enought to fit into most backpack bottle holders or cup holders. Plus, I love that you can lock it so I can put it in my bag without fear of it leaking!

05/08/2024 05:47 pm GMT

I hope you enjoyed these upper Midwest road trip itineraries and get a chance to try them out for yourself! Have you been on any of these? Share your experiences in the comments below!

If you want to hear more about the Upper Midwest or road trips like these, check us out at Road Trippers R Us!

As always, thanks for reading!

Kristi, aka The Trippy Tripster

road trippers

Meet the Author

Kristi is a fun-loving mother of three who enjoys traveling and taking road trips to fully experience life. She loves to seek out local eateries, off the beaten path hidden gems, and the best way to experience the most popular destinations. She shares her experiences to help others take the more scenic route and discover the beauty and adventures all around us. Read more about her journey and the places she’s uncovered at her blog and website at Road Trippers R Us .

You can follow Kristi’s road trip adventures at:
Facebook Page | Instagram | Pinterest


This post contains some affiliate links. If you choose to purchase items through these links, I will earn a small commission at no extra cost to you. These commissions help reduce the costs of running this site

Back to Blog

14 Responses to "5 of the Best Upper Midwest Road Trips"

Leave a Reply

Your email address will not be published. Required fields are marked *


Back to Blog