Memphis to Winona Road Trip: River Road Gems & Hidden Stops

The route from Memphis, Tennessee to Winona, Minnesota, roughly 750 miles, hugs the Mississippi River for much of the way via the Great River Road (National Scenic Byway). This is not a straight interstate shot—it’s a meandering path through bluffs, farmland, and river towns. The drive typically takes two to three days, but many travelers stretch it into a week-long exploration. A little-known fact: the lowest point of the entire drive (Memphis at 337 feet above sea level) contrasts starkly with the bluffs near Winona that rise over 1,300 feet, creating dramatic elevation changes along the river corridor.

Wondering how to find the best stops and hidden gems between cities? This guide breaks down every mile. We cover how long to drive Memphis, TN to Winona, MN, whether it is worth driving, and the best stops along the way.

The route passes through four major bioregions: the Mississippi Alluvial Plain (Tennessee/Arkansas), the Ozark Border (Missouri), the Driftless Area (Illinois/Wisconsin/Minnesota), and finally the Upper Mississippi River Valley. Each offers distinct vegetation, from cotton fields in the south to towering limestone bluffs in the north. The Driftless Area, missed by glaciers, features rugged karst topography and spring-fed streams.

Local commerce thrives in river towns. Hannibal, MO, Mark Twain’s boyhood home, offers riverboat tours. In Dubuque, IA, the Fenelon Place Elevator (a funicular) grants panoramic views. In Winona itself, the Minnesota Marine Art Museum features fine art with a maritime theme.

Culinary infrastructure ranges from barbecue in Memphis to cheese curds in Wisconsin. Must-try dishes: dry-rub ribs at Central BBQ (Memphis); toasted ravioli at Anthonino's Taverna (St. Louis); fried catfish at Big Muddy's (Cape Girardeau); and a Juicy Lucy at Matt's Bar (Minneapolis, a slight detour). For dessert, seek out frozen custard at Ted Drewes (St. Louis) or a slice of pie at the Mississippi Belle in McGregor, IA.

• Memphis: The Rendezvous (ribs), Gus's World Famous Fried Chicken.
• St. Louis: Pappy's Smokehouse (pulled pork), Imo's Pizza (St. Louis-style).
• Quad Cities: Whitey's Ice Cream (Moline), Happy Joe's (taco pizza).
• Winona: The Lake View Cafe (walleye), Blue Heron Coffeehouse.

Safety along the Great River Road is generally high, but caution is needed in fog-prone river valleys, especially near La Crosse, WI. Deer crossings are frequent around dusk in wooded stretches. Road shoulders are inconsistent—some sections have wide paved shoulders, others none. Emergency services are within 20 miles along most of the route. Keep a printed map or offline GPS as cell service fades in the Driftless Area.

For families, child-friendly stops include the St. Louis Zoo (free), the Magic House Children's Museum (Kirkwood, MO), and the National Mississippi River Museum & Aquarium (Dubuque, IA). Playgrounds are common at wayside rests; the rest area at mile 123 on US-61 (Illinois) has a modern play structure.

Fatigue management: Break your drive every 2 hours. Ideal rest zones with scenic overlooks include: Fort Defiance State Park (Cairo, IL), the Great River Road Interpretive Center (New Boston, IL), and Pikes Peak State Park (McGregor, IA). These have picnic tables and short walking trails.

Pet-friendly framework: Most state parks allow leashed dogs. Pet-friendly hotels include La Quinta Inn & Suites in Cape Girardeau and Motel 6 in Winona. For potty breaks, almost all rest areas have pet areas, but the one at mile 89 in Missouri is particularly large with a fenced dog run.

• Best family stop: St. Louis Science Center (hands-on exhibits).
• Best pet stop: Hickory Ridge Conservation Area (Bismarck, MO) off US-67.
• Hidden off-route spot: Trail of Tears State Park (Cape Girardeau, MO) offers solitude and a burial ground history.

The Great River Road alternates between divided highways and two-lane roads. Gas stations are plentiful near towns, but can be sparse between Cape Girardeau, MO and Alton, IL—plan to fill up. Tolls are absent on this route, but some bridges (e.g., Clark Bridge in Alton) have historical significance, not tolls. Road quality is generally good, with the best pavement in Missouri and Wisconsin sections. Watch for construction in the Quad Cities area (summer 2025).

• Best fuel stops: Sikeston, MO (exit 66, I-55); Hannibal, MO (US-61); Davenport, IA (I-80).
• Worst road stretch: US-61 through Missouri’s bootheel is rough in places; consider US-67 as alternate.
• Peak traffic: Avoid leaving Memphis on Friday afternoon between 3-6 PM (I-55 northbound congested).