I had the pleasure of doing a guest spot on the Amateur Traveler podcast recently, where I got to talk about the joys of traveling along the Mississippi River. Host Chris Christensen prefers to cover an itinerary of a week or so for the podcast, which is challenging when there are so many great itineraries to follow along the Mississippi.

Ultimately, I picked a 200-mile loop from Red Wing, Minnesota to La Crosse, Wisconsin and back; I thought it would best show off some of the highlights of the Mississippi Valley, like:

  • inviting small river towns
  • unique architecture
  • dramatic overlooks
  • a wealth of opportunities to get outside and explore (hiking, biking, paddling)
  • good places to eat
  • unique places to stay, and
  • a healthy dose of goofiness

Any trip along the Mississippi River begs for a slower pace, one where you take the time to enjoy the outdoors, to eat a relaxing meal, and to chat with people. This itinerary from Red Wing to La Crosse is perfect for that. Don’t overschedule; slow down and go deep instead of seeing the world through your car windshield.

The itinerary we talked about on the podcast is covered below. You can find out more about each community in the River Towns section at MississippiValleyTraveler.com; just follow the links I provide below.

This is one of the most scenic parts of the river, thanks to Lake Pepin, a natural lake in the river’s main channel where the water stretches three miles wide between tall limestone bluffs. From Wabasha, Minnesota to Rock Island, Illinois, much of the river is part of the Upper Mississippi River National Wildlife and Fish Refuge, so there is a lot of public land to explore.

Getting Started

Many people will drive their own car to explore this area, but if you’re coming from further away, you can fly into Minneapolis/Saint Paul International Airport or take Amtrak to Saint Paul (or La Crosse) and rent a car.

You can drive this itinerary any time of year, but most people will probably want to go when the weather is warm. Here’s an overview of what to expect in each season:

Summer: The time of year when most people will visit, summer on the upper Mississippi is a series of generally pleasant days with a few hot and humid ones mixed in. It’s also prime time for bugs, so if that bothers you, bring a repellent.

Fall: The busiest time of year along the upper Mississippi as people flock to the region for leaf peeping and the last of the season’s fresh produce, apples especially. A bonus for late fall: thousands of tundra swans create a spectacle as they pass through on their migration south and east.

Winter: You won’t be able to waterski, but there are no bugs! It’s a great time to visit if you love winter sports like skiing (cross-country and downhill), ice fishing, ice skating, or broomball. It’s also a great time of year to spot bald eagles, as they congregate in big groups in areas where there’s open water, like at Wabasha, Minnesota or just downriver of a dam. Keep your travel plans flexible, in case you get delayed by snow.

Spring: Spring is often wet and muddy, so hiking opportunities will be more limited, but if you’re able to get out, you’ll see a succession of beautiful spring flowers. Songbirds (and snowbirds) are also abundant as they migrate north to their summer homes. The weather can be highly variable: cold and wet one day and warm and dry the next, but again—there won’t be many bugs.

Red Wing (2 nights)

Red Wing is a popular destination for day trips from the Twin Cities, thanks to its charming old downtown and access to the river.

**Read the full Red Wing profile.


  • Hike up Barn Bluff
  • Ride the Cannon Valley Bike Trail
  • Take a river tour
  • Visit the Aliveo Military Museum
  • Visit the Goodhue County History Center
  • Go t