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 to the Sheldon Theatre for a show
  • Take a selfie next to the World’s Largest Boot
  • If you’re visiting in July, go to the Prairie Island Pow Wow (July)

Where to Eat

Dine at the Veranda at the St. James Hotel for a meal with a river view.

Where to Sleep

Stay at the St. James Hotel or one of the city’s fine bed-and-breakfast Inns.

On the Drive to Wabasha

  • Stop for a hike at Frontenac State Park
  • Visit Christ Episcopal Church in Frontenac , built in 1869 and largely unchanged since then
  • Stop in Lake City, where Ralph Samuelson invented waterskiing in 1922
    • Go for a walk along the lake
    • Take a sailboat tour or go hang gliding

**Want to know more about the places along the Mississippi River? Check out Road Tripping Along the Great River Road, Vol. 1. Click the link above for more. Disclosure: This website may be compensated for linking to other sites or for sales of products we link to.

Reads Landing/Wabasha (1 night)

Wabasha is a pleasant old rivertown, with a couple of good reasons to stick around for a day or two.

**Read the full Reads Landing profile and Wabasha profile.


  • Visit the Wabasha County Historical Society Museum
  • Visit the National Eagle Center
  • Take a kayak tour with Broken Paddle Guiding Company
  • If you’re in the area in February, join in the fun at Grumpy Old Men Days in February

Where to Eat

Eat at Slippery’s in Wabasha or at the Reads Landing Brewing Company.

Where to Sleep

Stay at the blufftop American Eagle Bluff Bed-and-Breakfast in Reads Landing or Turning Waters Bed-and-Breakfast in Wabasha.

On the Drive to Winona

  • Tour LARK Toys in Kellogg
  • Get a slice of pie in Kellogg at the Town and Country Café
  • Visit woodcarver Langseth Norsk Woodcarving in Minneiska
  • Hike to the top of the bluff at John Latsch State Park

Winona (2 nights)

Winona has a surprisingly active arts scene, which you can experience any time of year.

**Read the full Winona city profile.


  • Tour the Minnesota Marine Art Museum
  • If you’re visiting between late June and early August, go to the Shakespeare Festival
  • Tour the city’s architectural and stained glass treasures, including
    • Watkins Company Headquarters
    • The Egyptian-Revival Winona National Bank, with its second floor taxidermy collection
  • Tour the Bunnell House in Homer, an 1850s home built in the Steamboat Gothic style
  • Tour the Winona County History Center
  • Go to Garvin Heights for great views of Winona and the Mississippi Valley

Where to Eat

Get a bite to eat at the Lakeview Drive Inn, which opened 1938; if you happen to be visiting on a Wednesday, check out classic car night.

Another fine option is the Boat House Restaurant, which offers good river views and food made from seasonal ingredients.

Where to Sleep

Spend the night at the Alexander Mansion Bed-and-Breakfast, a 19th century Victorian showpiece.

On the Drive to La Crosse

  • Tour the pre-Civil War Pickwick Mill near La Moille, a six-story stone structure built along a scenic tributary of the Mississippi River.
  • Take a spin along the Apple Blossom Scenic Drive that connects the Minnesota communities of La Crescent and Dakota; besides beautiful views, look for flowering trees in May and fresh apples in fall.

La Crosse (2 nights)

La Crosse is a medium-sized city with plenty to keep you busy; many of the top attractions are outdoors activities.

**Read the full La Crosse city profile.


  • Drive to the top of iconic Grandad Bluff
  • Hike the winding trails at Hixon Forest
  • Take your bike for a ride on the Great River State Trail (24 miles) or the La Crosse River State Trail (22 miles)
  • Take your canoe, kayak, or stand-up paddleboard through the Mississippi River backwaters at Goose Island County Park
  • Tour the Hixon House, a mansion built in 1859 for a lumber baron with a fondness for Turkish style
  • Tour the Maria Angelorum Chapel at St. Rose Convent, a stunning Romanesque structure built in 1906 for the Sisters of Perpetual Adoration
  • Visit the World’s Largest Six-Pack
  • Tour the Mississippi Valley Archaeology Center at the University of Wisconsin – La Crosse for an overview of the indigenous civilizations and peoples who lived in the area

Where to Eat and Drink

Grab breakfast at Fayze’s, a long-time local favorite.

For a taste of modern American cuisine, dine at the Waterfront Restaurant and enjoy river views or relax in the retro modern style at Lovechild.

Enjoy a craft beer or the Turtle Stack Brewery or the Bodega Brew Pub, or a cocktail among the mid-century futurist decor at the Starlite Lounge.

Where to Sleep

Stay at the French-inspired Charmant Hotel downtown or in an old mansion at the Castle La Crosse Bed-and-Breakfast.

For something completely different, book a stay at the Bluff View House, a pre-fab all-metal Lustron house built in 1949.

On the Road to Fountain City

  • Hike through the Van Loon Wildlife Area near New Amsterdam, and its collection of floodplain forest and 100-year old bowstring bridges.
  • Hike and/or paddle at Perrot State Park in Trempealeau.

Fountain City (1 night)

Fountain City is a laid-back old rivertown with a strong river vibe.

**Read the full Fountain City profile.


  • Tour the Rock in the House, a bluffside home damaged by a falling boulder in 1995
  • Tour barns and sheds at Elmer’s Auto and Toy Museum

Where to Eat and Drink

Go deep locavore and eat at a pizza farm, like Suncrest Gardens, where they grow almost all of the ingredients that go on their pizzas.

Enjoy a drink at the Monarch Public House, which has been serving guests since the 19th century.

Where to Sleep

Stay at the Hawks View Cottages, which will feel like luxury treehouses.

On the Road to the Twin Cities

As you make your way back to the start of the route, there are a few more places to consider visiting. We were running out of time on the podcast, so I had to zip through these. You are free to take your time.

  • The overlook at Buena Vista Park in Alma offers one of the most spectacular views of the Mississippi Valley
  • Save an hour or two to tour two museums in Alma
    • The Castlerock Museum (the result of one collector’s obsession with medieval arms
    • The Alma Area Historical Society Museum, which has a wonderful collection of photographs from hometown photographer Gerhard Gessell who documented life in the town in late 19th and early 20th centuries
  • Laura Ingalls Wilder was born near Pepin, Wisconsin, which is why the town hosts a museum dedicated to her life
  • Up the road a piece, the Village of Stockholm has several art galleries and art-themed shops worth visiting
  • Save a little time to snack at the Stockholm Pie Company
  • Maiden Rock Bluff near Stockholm is one of my favorite blufftop locations, for the  views and blufftop plants and wildlife
  • Just down the road, the Maiden Rock Winery and Cidery creates English-style ciders from locally-grown apples
  • In the Village of Maiden Rock, pick up freshly baked goods at the Smiling Pelican Bake Shop

Make Plans to Come Back

No doubt you won’t be able to do all this, and you shouldn’t try. Like I said, take your time, get outside, chat with people, listen, share, rinse and repeat. And on the way back to the airport or Amtrak, you can check your calendar and block off time for your return visit.

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