A Getaway Along the Upper Mississippi River Leads to Small Towns, Big Views and Natural Wonders

When you cross a downed tree in the Mississippi backwaters, you have two choices: Go back where you came from or clamber over it—kayak and all. My inclination, facing such an obstacle, is to turn back. My skipper, Michael Anderson of Broken Paddle Guiding, has another idea. With deft maneuvering on his part, and wobbly-kneed stumbling on mine, we hoist ourselves out of our kayaks, haul body and boat over the dead tree, and continue down the sun-dappled back channels of Ol' Man River.

Broken Paddle is headquartered in Wabasha, Minnesota, but we launched our kayaks across the river, just south of Pepin, Wisconsin. A few hours into the trip, we've navigated 6 miles of enchanted flooded forest. Our route is part of the 261-mile Upper Mississippi River National Wildlife and Fish Refuge, easily accessible via the Great River Road.

This national scenic byway traces the Mighty Mississippi from its headwaters in northern Minnesota down to the Gulf of Mexico. Hundreds of charming river towns dotted with hole-in-the-wall bars, barbecue joints, and neo-Victorian bed-and-breakfasts line the route. My own three-day road trip covers 120 miles, crisscrossing three bridges joining Minnesota and Wisconsin, and focusing around Lake Pepin. Reaching 2 miles wide in places, it's the broadest naturally occurring part of the Mississippi and also the birthplace of waterskiing, invented nearly a century ago.

While some road-trippers book private sailing excursions across Lake Pepin (call Captain Beth at WIMNSail for details), and others soar above it with man-made wings (Eagle Hang Gliding has the ticket), I find Anderson's laid-back nature tour to be an excellent intro to the area. He expertly narrates the scenery around us. Silver maples over here. River birch over there. He also points out brilliant cardinal flowers and bald eagles perched high in the treetops. We stop to smell the swamp milkweed, with a scent like vanilla cotton candy, and watch the water dance on hydrophobic lily pads. We keep our fingers crossed for a sighting of a prothonotary warbler, identifiable by its chirpy call and happy yellow coat, but aren't so lucky. "They're hard to find anywhere else this far north," Anderson assures me. "They only like river backwaters and wetlands."

The ecology is just one reason Anderson is enamored with this swath of river country. The epic landscape is another. "There are towering bluffs 500 feet above the wild Mississippi River, and it's so easy to find peace and quiet," he says. "There's something about the deep forests, the views, the huge river valley—it feels ancient, a little mysterious even. It's a different kind of beauty out here."

A beauty in need of protection. The Lake Pepin Legacy Alliance, which Broken Paddle supports, is working hard to combat sediment accumulating in the upper end of Lake Pepin. Threatened by upstream erosion, both the lake and back channels are in danger of disappearing: The silt clouds the waters and destroys natural habitats. Anderson worries that the damage could be irreversible if they don't act immediately. His response? Share his wonderment with as many people as possible.

As we near the close of our tour, Anderson announces a surprise. It'll take some extra paddling, but he says it's worth it. We push past a boat of fishermen lazily jigging their rods for smallmouth bass and northern pike, through a swirl of kelly green duckweed, around several tall stands of reeds. And there she is: a lone American lotus rising from the inky black water. She was in full bloom yesterday, Anderson says. Today, just two buttery yellow oval petals cling to her showerhead-like stem. That's how fast things move around here. The message is clear: Hurry, go now, before it's gone.

Exploring the Minnesota Side of the Mississippi

Bookended by historic pottery in Red Wing and an astounding art collection in Winona, our route follows US-61.

What to Do

Iconic Red Wing hiking boots may get all the Instagram love—but the town's heritage ceramics get their own museum too in this town perfect for a weekend trip.

Pottery Museum of Red Wing displays 6,000 pieces of vintage stoneware (including two 70-gallon monster crocks) and shows how the clay-rich city was a magnet for earthenware companies in the late 1800s.

Just 15 miles south, Frontenac State Park spells paradise for bird-watchers. Follow 13 miles of trails to high bluffs, dense forest and restored prairie. Farther south, Lake City Marina loans bikes; tool around Lake Pepin to look for one of the Mississippi's only working lighthouses and Pepie the Lake Monster (Bluff Country's Nessie).

At Wabasha's National Eagle Center, families watch daily demos with rescued bald eagles. Scan for wild eagles from the observation deck.

Monet, Matisse, Picasso, Chagall—they're all part of the collection at Winona's Minnesota Marine Art Museum, which sits along Mississippi backwaters known as Yeomans Pond.

Where to Eat

Winona's old-fashioned Bloedow Bakery was founded in 1924, but the Bavarian cream donuts, maple long johns and glazed croissants taste as fresh as ever.

In Red Wing, grab a burger at Bev's Cafe downtown or have a sweet snack or a sandwich at Hanisch Bakery and Coffee Shop.

On the outskirts of Winona, Signatures Restaurant serves hearty meals of steak, fish, housemade pasta and hot sandwiches.

Where to Stay

In Red Wing, Round Barn Farm spreads over 35 idyllic acres, with a 1914 Dammon Round Barn listed on the National Register of Historic Places. The on-site B&B has five rooms, including the 800-square-foot Willow, with a fireplace, hanging swing and double jacuzzi.

Exploring the Wisconsin Side of the Mississippi

WI-35 from Hager City to Fountain City is one of the most scenic legs of the Great River Road. Just ask the dozens of Harley riders chasing its curves on a sunny afternoon.

What to Do

At Rush River Produce in Maiden Rock, hummingbirds dart in the wildflowers while you pluck currants, tart gooseberries and plump blueberries in July and August. Nearby, Cultural Cloth specializes in ethically sourced blankets, rugs and other textiles made by Indigenous women artists around the world.

Follow signs from State-35 along County-E to reach Buena Vista Park, 500 feet above Alma, for a great view of the Mississippi (and a nice place to picnic, too).

Start or end your travels on a spiritual note at Kinstone in Fountain City. The modern megalithic sculpture garden covers 30 acres overlooking the Mississippi. It features a meditation labyrinth, restored prairie, a dolmen with a 13-ton capstone and a thatched cordwood chapel for quiet contemplation.

Where to Eat

For all things pastry, hit up country-cute Stockholm Pie and General Store in Stockholm. Have a slice of old-fashioned sour cream raisin or order the daily pot pie special. Browse for souvenirs in the attached shop.

For picnic or snack supplies, head to Nelson Cheese Factory in Nelson. The 19th-century dairy building holds a modern shop with wine, cheeses and ice cream.

Homey Harbor View Cafe in Pepin has been a favorite in these parts since 1980. A rainbow of Adirondack chairs faces the water outside, and old books line the cozy interior walls.

Also in Pepin, clink glasses on a storybook piazza encircled by Italianate-style buildings at Villa Bellezza Winery, one of the 8 vineyards on the Great River Road Wine Trail.

Where to Stay

Two blocks from the Lake Pepin shore, Maiden Rock Inn in Maiden Rock ranks among the quirkiest B&Bs on the river. The 1906 high school building features restored pressed-tin ceilings, ornate custom woodwork and an artful spiral staircase.