What comes to mind when you think of the Midwest? Agriculture, maybe? That trademark “Midwest Nice”? Quirky accents and colloquialisms? There are many defining characteristics that shape the spirit of the Midwest, but perhaps one of the more noteworthy attributes of the heartland is its distinct four seasons.
From frigid, snowy winters and brisk, colorful falls to rainy springs and humid summers, the Midwest experiences the full spectrum of weather throughout the year. And with the varying seasons comes a wide range of activities to enjoy at distinct times.
Whether your group is considering a visit during the height of tourism season or the much colder offseason, there’s always plenty to do—both indoors and outdoors. It’s a veritable four-seasons playground, ripe with opportunity for fun, exploration, and relaxation.
WINTER
It can be intimidating to conquer the cold of a Midwestern winter—especially if you’re from somewhere slightly closer to the equator. But, if the snow is something your group is looking for, they’d be in the right place.
For the more active members of your group, consider a visit to a regional ski resort like Mount Ski Gull in Nisswa, Minnesota. Voted the No. 1 “Best Place for Winter Family Fun” by Best of The Brainerd Lakes, the resort offers 10 trails of varying difficulty levels for skiing and snowboarding, and there’s even a hill for tubing. Guests are able to rent equipment on-site.
In Portage, Wisconsin, visitors can ski, tube, and snowboard on 48 beginner, intermediate, and advanced trails at Cascade Mountain. The resort offers private and semiprivate lessons for small groups, and there are also on-site equipment rentals. Cascade even offers ski-in, ski-out day cabins your group can rent. These heated cabins, complete with a deck and outdoor fire pit, are great for gathering before and after hitting the slopes, eating lunch, and storing your group’s belongings during the day.
Of course, your group likely doesn’t want to spend too much time out in the cold. Consider taking a break at an indoor attraction like a local museum. In Milwaukee, Wisconsin, the Harley-Davidson Museum offers groups an in-depth look at one of the most iconic motorcycle brands in the world. The Art Institute of Chicago in Illinois is sure to astound the art aficionados of your group, as it boasts an expansive collection of work by visionaries like Vincent van Gogh, Georges Seurat, Diego Rivera, Georgia O’Keeffe, and Pablo Picasso. Learn about civil rights history at the National Underground Railroad Freedom Center in Cincinnati, Ohio, or explore Indigenous history at the Eiteljorg Museum of American Indians and Western Art in Indianapolis, Indiana.

Credit: Adobe/Ali Chehade Farhat
SPRING
No springtime visit to the Midwest is complete without a jaunt to Holland, Michigan, home of the annual Tulip Time festival. Tulip Time, slated for May 2-11, is a celebration of Dutch heritage and, of course, tulips! Every year, the Dutch-inspired community of Holland bears witness to the bloom of more than 6 million tulips throughout the city. During the festival, visitors to Holland can enjoy an array of programs, historic walking tours, artisan markets, cultural celebrations, and lots more—all while appreciating the beauty of the colorful flowers and windmills. Tulip Time even offers a concierge service to help group coordinators make the most of their trip and will work with groups to coordinate meals.
“Our job is to bring joy when the tulips bloom,” says Gwen Auwerda, executive director of Tulip Time. “We do that by having shows and entertainment every night and exhibits and displays every day. With our downtown shopping experience and meals specifically designed for groups, we make a group trip to Tulip Time seamless and easy while providing unforgettable memories.”
Auwerda says Tulip Time is more than just a few displays of tulips; it’s a city-wide infusion of colorful blooms, Dutch history, and cultural immersion. She adds that groups can get a behind-the-scenes look at how the city came to be and explore how the tulips came to be an integral part of Holland’s culture through step-on guided tours.
“While groups are in town, they can go on a public art tour and see the tulips on the walls of local businesses along with tons of other interesting pieces,” Auwerda says. “They can also visit the famous Big Red Lighthouse at Holland State Park; Bowerman’s Blueberry Farm with their on-site farm market; or Holland Bowl Mill, the largest producer of wooden salad bowls in the country.”
And even if you’re visiting Holland when it’s not Tulip Time, it’s still a gorgeous place to enjoy spring. The DeZwaan Windmill is an iconic tourist hot spot. Nelis’ Dutch Village offers an immersive experience that transports your group to the streets of Europe. Or, visit the DeGraaf Nature Center to explore the regional flora and fauna along wheelchair-friendly trails.
Spring is also a great time to visit Niagara Falls in Ontario, Canada. Although spring isn’t quite peak flow season for this quintessential attraction, visiting in the springtime means smaller crowds and lower prices. Averaging a flow rate of a whopping 675,000 gallons of water per second, this natural behemoth is a bucket list destination for many travelers.
While visiting, be sure to check out attractions like Journey Behind the Falls, where your group will be able to stand at the base of the Horseshoe Falls as the water crashes around them. For an unforgettable view, board the antique Whirlpool Aero Car, which takes tourgoers across the Whirlpool Gorge over the iconic Class 6 white water rapids.
Also open to visitors are the Butterfly Conservancy, Niagara Glen, Niagara Parks Power Station, the McFarland House, the Laura Secord Homestead, Old Fort Erie, Mackenzie Printery, and the Landscape of Nations living memorial.
SUMMER
Nothing says summer fun in the Midwest like a day spent out on a gorgeous lake. Groups should look no further than the “Land of 10,000 Lakes” for their summertime excursion. For an immersive dive into the natural wonder of Minnesota, the Boundary Waters Canoe Area Wilderness offers more than 1 million acres of pristine lakes and waterways, untouched forests, and picturesque bluffs. This 150-mile-long wilderness area contains more than 1,200 canoe routes, 12 hiking trails, and 2,000 designated campsites. The Boundary Waters aren’t for the faint of heart, though. Make sure to plan your group’s visit with the help of a local outfitter like River Point Outfitting Co. or Ely Outfitting Co., both of which offer guided trips, or consider a public tour with Border Lakes Tour Co.
Looking for something a little less rugged in the North Star State? The Twin Cities area—in addition to being a top summertime destination in the Midwest—is home to several popular lakes that are great for swimming, sailing, walking, picnicking, or catching a live musical performance. Lake of the Isles offers nearly 3 miles of shoreline and paved pathways. Bde Maka Ska, the largest lake in Minneapolis, offers watercraft rentals and sailing lessons and is a prime recreation spot. Or, consider Lake Harriet, a 335-acre body of water surrounded by parkland.
While Minnesota might be dubbed the “Land of 10,000 Lakes,” ask any Wisconsinite (like yours truly) which state really deserves the title, and they’ll tell you it’s the Dairy State that has more lakes to explore. (Minnesotans will tell you Wisconsin just defines “lakes” differently—we’ll let you be the judge.)

Credit: Olivia Curti
A great place to experience Wisconsin’s bountiful lakes is in the Minocqua region in the Northwoods. Home to recreational hot spots like Lake Minocqua, Clear Lake, Lake Tomahawk, Crystal Lake, Trout Lake, and many more, this quintessential northern community is paradise on Earth for those who love camping, fishing, boating, hiking, or simply being outdoors. Don’t be perturbed if camping isn’t quite your group’s speed, though; there are several lodging options available throughout the area, including The Waters of Minocqua and Pointe Hotel & Suites and Conference Center.
And, of course, you can’t go wrong with a visit to any of the Great Lakes’ shorelines in communities like Superior, Wisconsin; Mackinac Island, Michigan; Put-in-Bay, Ohio; or Toronto, Canada.
FALL
Although not peak tourist season in the Midwest, fall does have a major draw for groups: autumn colors. Known for their vibrant reds, oranges, and yellows, Midwestern falls make for some truly unforgettable views—if you know where to look, that is.
Minnesota’s North Shore is a great place to start. Climb aboard the North Shore Scenic Railroad for an excursion unlike any other. This 28-mile stretch of track between Duluth and Two Harbors brings groups on a colorful journey along the coast of Lake Superior. The railroad, which offers special rates for groups of 10 or more, features an array of excursion types—from the 75-minute “Zephyr Route” to the four-hour “Two Harbors.”
More popular places to witness fall colors are Lutsen, Minnesota; along the Great River Road National Scenic Byway in Illinois, which follows the Mississippi River; the M-119 “Tunnel of Trees” in Harbor Springs, Michigan; during a Parke County covered bridges tour in Indiana; or in scenic Door County, Wisconsin.
By Madeline Fuerstenberg
Main Image: Holland, Michigan; Credit: Tulip Time