9 Great Upper Midwest Vacation Ideas

From the Great Plains of North Dakota to the stunning shores and serene islands of Wisconsin and Michigan, the Upper Midwest is a treasure trove of natural beauty and cultural delights. Whether you’re seeking an epic cross-country adventure or a quick family weekend getaway, this region offers something for everyone. With charming villages, historic landmarks, national parks, and vibrant cities boasting culinary options and cultural attractions, you’ll never run out of things to see and do. These Upper Midwest Vacation ideas will inspire you to pack your bags, buckle up, and embark on a journey of a lifetime.

Here is what we’ll cover in this post:

collage with scenes from vacation locations in the Upper Midwest with the superimposed text that reads: Upper Midwest Vacation Ideas

9 Great Upper Midwest Vacation Ideas

Chicago, Illinois

skyline of Chicago, Illinois
Via Unsplash. Used by permission (public domain).

Nestled on the shores of Lake Michigan, the Windy City of Chicago is an iconic destination that offers endless possibilities for exploration and adventure. Whether you’re a foodie, a history buff, a culture vulture, or a nature lover, this Upper Midwest vacation idea has something for you.

Begin your journey with a stroll along the Magnificent Mile, a world-famous shopping district that features high-end retailers, luxury boutiques, and renowned department stores. If you’re an art enthusiast, the Art Institute of Chicago is a must-see destination that boasts an extensive collection of American and European masterpieces. For history buffs, the Chicago History Museum offers fascinating exhibits and interactive displays that showcase the city’s rich and varied past.

No trip to Chicago is complete without indulging in the city’s iconic cuisine. Whether you’re craving deep-dish pizza, Chicago-style hot dogs, or authentic ethnic cuisine, the city’s diverse culinary scene is sure to delight your taste buds.

From Millennium Park’s iconic Bean sculpture to Navy Pier’s thrilling amusement rides, Chicago is a city that never runs out of things to see and do. So why wait? Plan your visit to the Windy City today and experience the magic of this incredible city for yourself.

Mackinac Island, Michigan

Buildings on Mackinac Island, Michigan.

Located on the pristine shores of Lake Huron in the Upper Midwest, Mackinac Island is a captivating destination that boasts a unique way of life and a rich history. Visitors can explore the island’s natural beauty and historic landmarks at a leisurely pace, whether by foot, bicycle or horse-drawn carriage, as cars are prohibited on the island.

One of the island’s most iconic landmarks is the Grand Hotel, a majestic Victorian-era hotel that has welcomed presidents, royalty, and celebrities for over a century. Guests can enjoy the hotel’s grandiose décor, fine dining, and world-class amenities, while experiencing the island’s rich history.

In addition to the Grand Hotel, Mackinac Island has a range of other historic sites, such as Fort Mackinac, a 19th-century military outpost that offers stunning views of the island and surrounding waters.

With a plethora of activities and attractions, from hiking and kayaking to shopping and dining, Mackinac Island offers something for everyone. And with its stunning natural beauty and quaint small-town atmosphere, it’s no wonder why Mackinac Island is one of the Upper Midwest’s most beloved destinations. So, come and immerse yourself in the enchanting world of Mackinac Island, and make unforgettable memories that will last a lifetime.

Black Hills, South Dakota

Black Hills
Via Unsplash. Used by permission (public domain).

Situated in the rugged terrain of the Upper Midwest, the Black Hills of South Dakota is a breathtaking destination that offers a wide range of activities and attractions for visitors. From hiking and biking to exploring historic landmarks and taking in scenic drives, the Black Hills have something for everyone.

One of the region’s most iconic landmarks is Mount Rushmore National Memorial, a massive sculpture carved into the mountainside that depicts the faces of four of America’s greatest presidents. Visitors can learn about the history and significance of the monument and take in the awe-inspiring views of the surrounding Black Hills.

The Black Hills are also home to Custer State Park, a vast wilderness area that offers abundant wildlife viewing opportunities, including bison, elk, and bighorn sheep. The park’s scenic drives and hiking trails are also popular attractions, offering visitors a chance to immerse themselves in the stunning natural beauty of the area.

Other notable attractions in the Black Hills include the Crazy Horse Memorial, a massive sculpture in progress that honors the legacy of Native American leaders, and the Badlands National Park, a unique landscape of eroded buttes, pinnacles, and spires.

So, whether you’re seeking adventure, history, or natural beauty, the Black Hills of South Dakota are a must-visit destination in the Upper Midwest. Plan your trip today and experience the magic of this incredible region for yourself.

Door County, Wisconsin

waves crashing into cliffs at Cave Point County Park

Located on the eastern coast of Wisconsin in the Upper Midwest, Door County is a charming destination that is known for its scenic beauty, picturesque towns, and outdoor activities. Visitors to the area can explore the 300 miles of shoreline that hugs the peninsula, dotted with historic lighthouses, sandy beaches, and rocky bluffs.

One of the region’s most popular attractions is the Door County Maritime Museum, which tells the story of the area’s rich maritime history. Visitors can tour historic vessels, see exhibits on shipbuilding and commercial fishing, and learn about the region’s unique relationship with the Great Lakes.

For outdoor enthusiasts, Door County is a paradise, with opportunities for fishing, boating, kayaking, and hiking. The area is also home to several state parks, including Peninsula State Park, which offers stunning views of Green Bay and miles of hiking and biking trails.

Door County is also renowned for its culinary offerings, with an abundance of locally sourced ingredients and a thriving food scene. From artisanal cheeses and wines to fresh-caught fish and locally grown produce, the area’s restaurants and markets showcase the best of the region’s culinary traditions.

With its scenic beauty, rich history, and endless activities, Door County is a must-visit destination in the Upper Midwest. Whether you’re seeking adventure, relaxation, or a taste of local culture, Door County is sure to enchant and delight. So, plan your trip today and experience the magic of this special corner of Wisconsin.

Boundary Waters in Minnesota

canoe with fishing rods on a lake
Via Unsplash. Used by permission (public domain).

Tucked away in the heart of the Upper Midwest, the Boundary Waters Canoe Area Wilderness is a pristine wilderness area that encompasses over a million acres of rugged forests, glimmering lakes, and cascading waterfalls. This unspoiled wilderness is a paradise for outdoor enthusiasts, offering unparalleled opportunities for canoeing, camping, fishing, and hiking.

The Boundary Waters is a paddler’s dream come true, with over 1,200 miles of canoe routes that wind through the interconnected waterways of the area. Visitors can explore the vast network of lakes and rivers, watching for wildlife and soaking in the peaceful beauty of the area.

For those who prefer to hike, the Boundary Waters also boasts miles of hiking trails that offer stunning views of the surrounding wilderness. Visitors can trek through old-growth forests, cross crystal-clear streams, and scramble up rocky ridges for unforgettable views of the area.

One of the most unique aspects of the Boundary Waters is its sense of isolation and solitude. With no motorized vehicles allowed in the wilderness, visitors can experience a true sense of peace and quiet, immersing themselves in the beauty and serenity of this special place.

So, whether you’re seeking adventure, solitude, or simply a chance to reconnect with nature, the Boundary Waters is a must-visit destination in the Upper Midwest. Plan your trip today and experience the magic of this incredible wilderness for yourself.

Twin Cities of Minneapolis and Saint Paul, Minnesota

Minneapolis skyline at night.
Via Unsplash. Used by permission (public domain).

Located in the Upper Midwest, Minneapolis and St. Paul form the Twin Cities, an exciting destination that offers something for everyone. Situated along the banks of the mighty Mississippi River, this area provides a combination of natural beauty, cultural richness, and urban charm that has been captivating visitors for years.

Outdoor enthusiasts will find plenty to do in the Twin Cities, with numerous parks and lakes to explore, including the Chain of Lakes which is popular for swimming, boating, and fishing. The region also offers a thriving arts and culture scene, with world-renowned museums, theaters, and galleries, such as the Walker Art Center and the Minneapolis Institute of Art.

The local cuisine is not to be missed, featuring traditional Midwest dishes and farm-to-table restaurants. From quaint diners to elegant restaurants, the area has a diverse and exciting food scene.

In addition to its natural beauty, cultural richness, and exciting cuisine, the Twin Cities are also home to one of the world’s largest malls, the Mall of America. This sprawling complex is a destination in itself, featuring over 500 stores, an indoor amusement park, an aquarium, and many other attractions. It’s a perfect spot for shoppers and families looking for a day of fun and entertainment. With so much to see and do, the Mall of America is a must-visit destination that truly sets the Twin Cities apart from other metropolitan areas in the Upper Midwest.

Plan your trip today and discover why the Twin Cities are a destination that won’t disappoint. Experience the beauty, culture, and flavors of the Upper Midwest by visiting this unique region.

Wisconsin Dells

Photo of Dells in the Wisconsin River.
Via Unsplash. Used by permission (public domain).

Located in the heart of the Upper Midwest, Wisconsin Dells is the second most popular tourist destination in Wisconsin, after Milwaukee. This spectacular natural wonder boasts a mesmerizing blend of serene landscapes and outdoor adventure. This area features a remarkable collection of river gorges and rock formations that have been sculpted over millions of years by the Wisconsin River, offering visitors the chance to take a scenic boat tour or explore the hiking trails.

The region is also known for its family-friendly attractions such as water parks, amusement parks, mini-golf courses, and go-kart tracks, making it a popular destination for families with children. Moreover, Wisconsin Dells is a paradise for food lovers. From traditional Wisconsin cheese dishes to classic American fare, visitors can indulge in a variety of delicious and diverse cuisines.

Wisconsin Dells is a must-visit destination for anyone looking to experience the unique natural beauty, outdoor adventure, and family fun that the Upper Midwest has to offer.

Traverse City, Michigan

sand beach at Whitefish Dunes State Park in Door County, Wisconsin.
Via Hello Door County.

Traverse City, Michigan is a great vacation destination located in the heart of the Upper Midwest. With its stunning natural beauty, vibrant arts and culture scene, and endless outdoor recreational opportunities, it’s no wonder why this charming town has become a beloved destination for tourists from all over the world.

The town’s prime location on the shores of Lake Michigan makes it a perfect spot for water-based activities such as swimming, boating, and fishing. It is also surrounded by rolling hills and lush forests, which provide endless opportunities for hiking, biking, and exploring the outdoors. During the fall, the town transforms into a kaleidoscope of colors as the leaves change, making it a popular destination for leaf-peeping enthusiasts.

Traverse City is also home to a thriving arts and culture scene, with numerous galleries, theaters, and museums showcasing the region’s rich history and artistic heritage. Visitors can also indulge in the town’s world-renowned culinary scene, which offers a diverse array of cuisine made with locally sourced ingredients, including fresh seafood from the Great Lakes.

Overall, Traverse City, Michigan is a fantastic vacation destination that offers something for everyone. Whether you’re looking to relax and unwind in a serene natural setting or explore the town’s vibrant arts and culture scene, you’re sure to find something that suits your interests and preferences.

Minocqua, Wisconsin

Minocqua, Wisconsin, is a fantastic vacation spot in the Upper Midwest, chock-full of outdoor activities and fun attractions. First and foremost, the area is home to a plethora of stunning lakes that offer swimming, boating, and fishing opportunities galore. If you’re feeling adventurous, take a kayak or canoe out and explore the scenic shoreline. And if you’re more of a landlubber, there are plenty of hiking and biking trails that will take you through lush forests and past breathtaking waterfalls.

But Minocqua isn’t just about nature – the town also boasts a charming downtown area with plenty of shops and restaurants to explore. And if you’re looking for some family-friendly fun, check out the Northwoods Wildlife Center, where you can see live animals up close and even attend educational programs.

All in all, Minocqua is the perfect vacation destination for anyone looking to get away from the hustle and bustle of city life and immerse themselves in the natural beauty of the Upper Midwest. It’s truly a hidden gem that not many people know about, so be sure to add it to your travel itinerary!

What Is the Upper Midwest?

The Upper Midwest is a region of the United States that includes the states of Minnesota, Wisconsin, Michigan, Iowa, North Dakota, South Dakota, and sometimes parts of Illinois, Indiana, Ohio, and Nebraska. It is characterized by its location in the northern part of the country, its cold winters and hot summers, and its abundance of lakes and forests. The region is known for its strong Scandinavian and German heritage, as well as its agricultural industry, which includes crops such as corn, soybeans, and wheat. Major cities in the region include Minneapolis, St. Paul, Milwaukee, and Detroit. The Upper Midwest has a rich cultural history and is home to numerous museums, galleries, and cultural institutions.

Why Vacationing in the Upper Midwest Is a Great Idea

The Upper Midwest is a great place to vacation, offering a unique blend of natural beauty, outdoor recreation, and cultural attractions. During the summer months, cooler temperatures provide a welcome respite from the heat, and the region’s many lakes offer opportunities for swimming, boating, and fishing. The Great Lakes, in particular, provide endless opportunities for outdoor adventure, with miles of beaches, hiking trails, and scenic overlooks. In the winter, the region transforms into a winter wonderland, with abundant snowfall providing ample opportunities for skiing, snowmobiling, ice fishing, and more. With a rich cultural history and numerous museums, galleries, and festivals, the Upper Midwest is a destination that offers something for everyone.

Frequently Asked Questions

What are some popular outdoor activities to do in the Upper Midwest?

The Upper Midwest offers a plethora of outdoor activities, including hiking, biking, fishing, boating, and swimming in the summer. In the winter, skiing, snowboarding, ice fishing, and snowmobiling are popular activities.

When is the best time to visit the Upper Midwest?

The best time to visit the Upper Midwest depends on what activities you’re interested in. Summer is great for outdoor recreation and festivals, while fall offers stunning foliage and harvest festivals. Winter is perfect for snow sports, and spring brings beautiful wildflowers and birdwatching opportunities.

What are some must-see attractions in the Upper Midwest?

Some must-see attractions in the Upper Midwest include the Mall of America in Minnesota, the Wisconsin Dells waterpark, Mackinac Island in Michigan, and Mount Rushmore in South Dakota. There are also many national and state parks, museums, and cultural attractions to explore.

About the author
Mark Stoneman
Hi! My name is Mark! I have been a resident of Door County for almost ten years now, and I'm glad to help you say "Hello" to Door County. I believe that travel helps to change lives, and because of that, I want to help you improve your life through travel.