Great River Road Wine Trail

The Great River Road Wine Trail connects wineries near the Upper Mississippi River in Minnesota, Wisconsin, and Iowa. It’s a wine-country road trip built around river towns, bluff views, and tasting rooms—not a compact cluster you can cover on foot. The Great River Road follows designated scenic highways on both sides of the Mississippi, and the drive deserves room in your itinerary.

What visiting is actually like

Expect variety rather than a single tasting-room style: a downtown tasting bar in a historic building, a vineyard setting, an Italian-inspired piazza, or a grapevine-lined wine garden. The wines vary, too, with cold-climate grapes, fruit wines, and cider among the offerings. You don’t need to arrive knowing your preferred grape; telling the person pouring whether you like dry or sweet is a useful start.

Plan for two or three tastings in a day within one area, with time for lunch and a riverfront walk. That’s a suggested pace, not a challenge. The trail stretches across several town clusters, and some wineries sit inland rather than directly beside the river. Trying to stitch every area into one day would turn the trip into mostly windshield time.

Where to base your trip

• Stockholm or Pepin, Wisconsin: A good choice for a small-town stay around Lake Pepin, with shops, places to eat, and river views between visits.
• Winona, Minnesota, or Fountain City and Trempealeau, Wisconsin: Useful bases for exploring both sides of the river, with museums, parks, and bluff-country outings alongside tastings.
• La Crosse, Wisconsin: A practical base for combining wine stops with downtown dining and a riverfront walk.
• Marquette, Iowa: Choose this river town for a southern-area visit that can also include Effigy Mounds National Monument.

When to go and how to plan

Late spring through fall is the best fit if you want outdoor seating and time exploring the river towns. Autumn is especially appealing for a scenic drive; the trail’s Toast to Harvest wine-and-food tasting event takes place in October. Check the current event details before planning around it.

Winter visits are possible, but don’t assume every tasting room keeps the same schedule. Download the trail’s wine map, group nearby visits, and confirm individual hours, tasting fees, and reservation requirements before leaving. Leave room for bridge crossings when switching riverbanks, and arrange a designated driver. An afternoon works for one area; a weekend gives the river towns their due.