The Mississippi River Valley

Start in Galena, where 85% of the buildings are on the National Register of Historic Places. This 1850s lead mining town looks like it was preserved in amber—Ulysses S. Grant's home still stands on the hill above Main Street. Spend a full day here: morning coffee on the brick-lined streets, afternoon browsing the antique shops, evening dinner at one of the historic inns. This town deserves your time, not a quick stop.

Galena

Illinois

A remarkably preserved 1800s Main Street nestled in rolling hills—once home to Ulysses S. Grant.

Head north along the Great River Road (US-61)—it's slower than the interstate but that's the point. You'll pass through river towns and bluff-top overlooks before reaching Winona, stretched beneath Sugar Loaf bluff—a Victorian gem with an emerging arts scene. After lunch, head inland through the bluff country to Lanesboro, tucked in a valley where the Root River State Trail brings cyclists and the Commonweal Theatre brings culture to a town of 700. This is B&B country—book ahead and settle in for the evening.

Winona

Minnesota

A Mississippi River gem with Sugar Loaf landmark, Victorian architecture, and a thriving arts scene.

Lanesboro

Minnesota

The Bed & Breakfast Capital of Minnesota, nestled in bluffs with world-class biking trails.

Head back to the Mississippi and continue north to Red Wing, where Barn Bluff rises 340 feet above the river and the historic St. James Hotel anchors a Main Street of red brick storefronts. In the afternoon, cross to the Wisconsin side and drive 20 minutes south to Stockholm—a village of 66 people with galleries, a legendary pie shop, and views across Lake Pepin. Return to Red Wing for the night or continue north toward the Twin Cities.

Red Wing

Minnesota

Historic Mississippi River town with stunning bluffs, famous pottery and shoe heritage.

Stockholm

Wisconsin

Tiny artist village on Lake Pepin known for pie that's worth driving across state lines for.

Head west into the Minnesota River Valley for a change of scenery. New Ulm is a genuine slice of Bavaria on the prairie—the Glockenspiel plays three times daily, Schell's Brewery has been pouring since 1860, and the Hermann Monument towers over town like a guardian of the old country. Take your time here—tour the brewery, climb the monument, and have dinner at a German restaurant before continuing north.

New Ulm

Minnesota

A slice of Bavaria in Minnesota with the iconic Glockenspiel and America's second-oldest family brewery.

Start in Northfield, whose motto tells you everything: "Cows, Colleges, and Contentment." This is where Jesse James's gang tried to rob a bank in 1876 and got run out of town by the locals. Carleton and St. Olaf colleges give the town a youthful energy. After lunch, drive an hour northeast to end your trip in Stillwater on the St. Croix River—Victorian architecture, antique shops, and the iconic Lift Bridge. From here, it's an easy 30 minutes to Minneapolis–St. Paul.

Northfield

Minnesota

Historic college town where Jesse James met his match, with two great colleges and small-town charm.

Stillwater

Minnesota

Minnesota's birthplace on the scenic St. Croix River, featuring Victorian architecture and antique shops.