Skip to site content
Group Travel Leader Group Travel Leader Group Travel Leader

Heartland Waterfronts Wow Groups

It may not have ocean access, but America’s Heartland offers an abundance of lovely waterfront locales. There’s plenty to do and see in places like the Chicago Riverwalk; the Mississippi River in the Quad Cities and St. Louis; Wisconsin’s Lake Michigan; and the three rivers of Fort Wayne, Indiana. 

These attractions are interesting enough to draw visitors to the region and can be the keystone to a great group getaway in the Midwest. 

Lake Michigan 

Water Trail Wisconsin

Wisconsin may not boast as many lakes as neighbor Minnesota, but it does have Lake Michigan, the fifth-largest freshwater lake in the world and home to the amazing Lake Michigan Water Trail. Eventually, this watery paradise will be the aquatic version of the legendary Appalachian Trail and the longest continuous loop water trail in the world. When completed, it will comprise a 1,600-mile waterway that hugs the Great Lake’s scenic shoreline. 

The Wisconsin section of the trail starts near Kenosha on the east side of the Badger State and runs all the way around the Door Peninsula, the so-called Cape Cod of the Midwest, for roughly 525 total miles. Natural highlights along the route include the hidden gem Rock Island State Park in Door County, the sand dunes at Kohler-Andrae State Park near Sheboygan, and Manitowoc’s Two Creeks Buried Forest, a petrified pine forest under the waves. 

Door County Kayak Tours can accommodate groups of up to 24, though most companies prefer to keep it closer to 15 because that’s how many fit into the small shuttle buses used to ferry guests to the water. For those who prefer an urban excursion, Brew City Kayak has both simple rentals and guided tours of the Milwaukee waterfront. The Milwaukee Kayak Company can also accommodate groups of up to 22 and has the most guided tour options in the city.

Three Rivers of Fort Wayne

Fort Wayne, Indiana

Indiana’s second-largest city, Fort Wayne, is situated on three rivers, which helps to create a dynamic downtown environment groups will love. The St. Mary’s, Maumee and St. Joseph rivers come together to form eight miles of riverfront in this Hoosier State destination. Much of that riverfront remains in its natural state, making it ripe for paddlers, including up to 20 kayakers with River City Fort Wayne. Stand-up paddleboards, canoes and small boats offer other ways to ride the river. For a motorized option, Fort Wayne’s replica canal boat fits up to 38 passengers; groups of 25 or more can charter a full boat. 

Travelers interested in hiking can enjoy the Rivergreenway Trail, which follows the river all the way to nearby New Haven. Additionally, Promenade Park is where the city meets the natural world and has a kids’ canal, a tree canopy trail, porch swings, an amphitheater, a pavilion and more to keep groups of all ages entertained.

Mississippi River

Quad Cities, Iowa 

The Quad Cities comprise Davenport and Bettendorf in Iowa and Rock Island and Moline on the Illinois side of the Mississippi River. Between them runs the mighty Mississippi River, the second-longest waterway in the United States. In addition to this quartet of cities, small nearby town Le Claire has a cute main street and serves as a jumping-off point to explore the water in two ways. 

First, the Riverboat Twilight offers one- and two-day cruises on a refurbished Victorian-era riverboat and cruises from May to October. For those with less time to spend in the Quad Cities region, a 90-minute sightseeing option is also a great way to get a taste of the river town. 

Another way to get on the water is through Celebration River Cruises, which also has a Le Claire port as well as another Quad Cities port on the Illinois side. This large paddle-wheel boat can accommodate up to 800 passengers, making it the biggest nongaming riverboat in the northern reaches of the river. Groups can take sightseeing cruises or enjoy a meal on lunch and dinner cruises. 

Small groups of six can book the Tiki Tavern in nearby Princeton, Iowa, an island-themed boat experience that comes with a captain. Tours vary in length from two to four hours for this tropical good time. Active groups can consider a guided kayak tour through Quad Cities Kayak River Adventures, which has Rock Island and Mississippi River tours of varying lengths, from two and a half hours to eight hours. 

For a beverage after the tour complete with gorgeous river views, groups can head to the small-batch Mississippi River Distilling Company in Le Claire.

Illinois Riverwalk 


While the Windy City may be better known for Lake Michigan, its Chicago Riverwalk along the eponymous river is another impressive spot. Open daily from 6 a.m. to 11 p.m., this 1.25-mile pathway winds through four districts. The Riverwalk boasts multiple public art installations such as murals and Art on the Mart, a massive nighttime digital art project that may be the largest of its kind in the world. 

Groups can book a Chicago architecture cruise on the water through First Lady Tours, which can accommodate private groups of as few as two to as many as 250. For those who’d like to power their own exploration, consider a Chicago Cycleboats trip for as many as 26 passengers. Both guided tours and solo rentals, even first-time paddler options, are available at Urban Kayaks at their Riverfront location. 

An extra-sustainable waterfront experience can be curated by the zero emission-certified Chicago Electric Boats, which has the option to rent a self-guided vessel for up to 12 visitors. Groups should enjoy the numerous restaurants and bars that pepper this 1.25-mile stretch of the Chicago River, as the city is a major culinary and beverage capital.

Missouri Riverfront 

St. Louis 

One of the most recognizable landmarks in the United States is the Gateway Arch in St. Louis, Missouri. Adjacent to this urban national park, the 1.5-mile riverfront promenade is the site of community events such as music festivals throughout the year. 

For visitors, the best way to get out on the water is via the Riverboats at the Gateway Arch, which offers two multitiered replica paddle boats to cruise in style. Guests can experience an hourlong sightseeing cruise of the industrial riverfront or a skyline dinner cruise that features live music and a meal, among other specialty cruises held throughout the year. Past special events cruises have included Octoberfest, a Sunday chef’s supper club, ghost cruises and a blues cruise that paid homage to the long musical history of the Gateway City. Large groups can be accommodated with a private charter for up to 220 passengers.

On the land side, there’s a 12-mile St. Louis Riverfront Trail that runs from the Laclede’s Landing warehouse district all the way to the Old Chain of Rocks Bridge, a Route 66 highlight. This bike and pedestrian path is part of the River Ring, a large network of trails administered by the Great Rivers Greenway.