The Midwest is one of the most underappreciated regions in the United States. With cities like Chicago and picturesque scenery along the rugged shores of Lake Superior, there are an endless number of places to explore. Whether you’re looking for an urban adventure or to slow down and reconnect with nature, the Midwest holds varied landscapes, like lush forests, serene lakeshores, waterfalls, caves, and caverns, plus so much more. Apple festivals, berry festivals, and arts festivals fill the year with things to do, and friendly communities welcome people into their towns. We will always be ready for a coastal escape, but you can also find us making our way through the slower-paced, diverse goldmine that is the Midwest.

*Holland, Michigan - Photo Credit (link*)

Bayfield, WI & the Apostle Islands

In the northern tip of Wisconsin near Lake Superior, Bayfield offers a secluded retreat surrounded by lush forests and rocky shores. Bayfield serves as a harbor town with direct access to the breathtaking Apostle Islands - 22 islands known for their beautiful rock formations, caverns, and lighthouses. Explore a variety of beaches across the region with different landscapes and views, take a ferry ride to the various islands, or stick to the mainland, hiking or biking miles of coastline and trails. Bayfield is known for its arts scene with plenty of live entertainment, galleries, and shops to peruse. For a trip focused on wellness, consider staying at Wild Rice Retreat, named as one of the top destination spa resorts by Conde Nast Traveler. Wild Rice offers a range of accommodation options, allowing guests to join guided retreats or book a resort stay to curate their own experience.

Charlevoix, MI

Located on an isthmus between Lakes Michigan and Charlevoix in the northwest corner of Michigan, Charlevoix is a charming Midwestern town that embraces a slower pace of life. With a lively downtown filled with independently owned boutiques and restaurants, fairy tale-inspired houses, and more lakefront than you’ll know what to do with, it’s a beautiful place to spend time slowing down. Soak in each moment and take your time exploring one of the many trails that go through nature preserves or along the lakefront with the calming sounds of the water. Grab a coffee in one of the cozy coffee shops in town, indulge in a pastry or two, or sip through a wine tasting with spectacular views of the drawbridge and lakes. Get on the water with a catamaran ride, take in the sweeping sunsets near a lighthouse, and kick your feet up with a good book. Regardless of how you choose to spend time in Charlevoix, it’s a town worth coming back to for a well-deserved retreat.

Chicago, IL

The largest city in the Midwest and one of the largest in the United States, Chicago is a unique urban landscape with a vibrant, busy downtown and a lakefront that runs the entire length of the city. Chicago is the ideal destination for any type of traveler. Solo travelers will feel far from lonely in this friendly city. Those who love being surrounded by nature have eighteen miles of the Lakefront Trail to explore either on foot or by cycling. Travelers who prefer to slow down and relax will find plenty of places to do just that, whether it’s leisurely exploring one of the city’s neighborhoods like Lincoln Square or lounging on a daybed at North Avenue’s Shore Club. Adventure and thrill seekers can TILT over the city at the Hancock Tower or kayak along the Chicago River. Foodies are in one of America’s most dynamic restaurant cities with award-winning bites from hole-in-the-wall long-time institutions to Michelin-starred restaurants. A friendly city with a Midwestern vibe, everyone feels welcome in Chicago, and there are endless things to do, making it a city you’ll want to return to.

Galena, IL

Located across the Mississippi River from Iowa, Galena is an idyllic town known for its representation of 19th-century architecture and deep ties to American history. Stay in one of many charming bed and breakfasts or a luxury resort. Step into Galena’s nature-filled surroundings from river cruises to hikes through the hilly, verdant landscape. Stroll down the Historic Main Street and enjoy wine tastings, local breweries, delicious locally-inspired restaurants, boutique and antique shops, art galleries, and more. There’s plenty to do, but for those interested in exploring outward, visit neighboring Elizabeth or head over the border to discover Dubuque for a change of scenery and pace.

Grand Marais, MN

Also located along Lake Superior, Grand Marais, Minnesota, is another picturesque place perfect for slowing down and reconnecting with nature. Like many smaller Midwestern towns, Grand Marais has a bustling arts community in a walkable town with scenic views, charming old architecture, quaint restaurants, and much more. The thing about Grand Marais that earned it a spot on this list is its stunning shoreline and natural elements, starting with Artist’s Point. This edge of land on Lake Superior is a spectacular place to catch a sunrise (and even sunset). Trails will take you through the rugged landscape of the region, like Grand Portage, where you can see stunning waterfalls. See Grand Marais from above by taking a hike up Pincushion Mountain - a particularly incredible sight in the fall when the trees have all turned colors. Don’t miss Cascade River State Park with hiking options for every skill level that result in unforgettable views of even more beautiful waterfalls.

Hocking Hills State Park, OH

One might argue that Hocking Hills is the most beautiful part of Ohio, and it’s not difficult to understand why. Located in the southeastern part of the state in the foothills of the Appalachian Mountains, Hocking Hills State Park is known for stunning waterfalls and caves. Whether you visit in the summer when everything is lush and green, or in winter when the falls are frozen over and everything feels like a fantasy winter wonderland, the beauty of Hocking Hills draws people back time and time again. A true nature getaway, Hocking Hills State Park offers a variety of outdoor activities from horseback riding to rock climbing, hiking to kayaking, and plenty more. See the landscape from above with ziplining in the tree tops, or see the forest by water while paddling a canoe. The area offers many different types of accommodation, from traditional camping to resorts and cabin rentals. Regardless of how you plan your visit, don’t forget to look up. Hocking Hills is known for its spectacular stargazing views.

Holland, MI

Located less than twenty minutes from the popular lakeshore town of Saugatuck, Holland is a cute Michigan town known for its Dutch influence and scenic beaches. You might be familiar with Holland from the photos of its famous windmill among a field of tulips, similar to what you’d see in the Netherlands. Explore Holland’s downtown area, a destination worthy of a Hallmark movie. Grab a European pastry, browse galleries and boutiques, or grab a bite at one of the fabulous restaurants before antique shopping. While Holland is not located directly on Lake Michigan, it’s only a short fifteen-minute drive and worth the trek. With breathtaking sunset views, crystal clear blue waters, and a stunning shoreline, you might never want to leave.

Omaha, NE

The Midwest is no stranger to small and mid-size cities. With options like Madison, Milwaukee, and Minneapolis, some of the less-traveled are often overlooked, like Omaha. The Nebraska city has done a lot of revitalization work in the past two decades to draw in visitors and bring Omaha into the future. While there’s no shortage of historic buildings in Omaha, you can see older districts with a new, vibrant energy like The Old Market. It used to be the warehouse district and is now a buzzing destination filled with restaurants, artists, makers, shops, and more. The Omaha RiverFront is another recently completed project that might be said to have brought the city back to life. The project spans three different parks with trails, sports, performance areas, and more. Visit The Joslyn Art Museum, recently re-opened after a two-year renovation, for over five thousand years of human creativity represented. Finally, stand in two states at once on the Bob Kerrey Pedestrian Bridge, which lords over the Missouri River, bridging Nebraska and Iowa.