In La Crosse, Wisconsin, hop on the Great River Road National Scenic Byway (wigrr.com) and follow the route south along riverside bluffs. (Be sure to stop at the camera-worthy overlooks.)
From the byway, head east 12 miles on State-171 to the small town of Gays Mills (gaysmills.org). A cluster of apple trees on the west side of town welcomes visitors with bright blooms, but keep following the highway east until it climbs out of the Kickapoo River Valley to the five farms on Orchard Ridge (gaysmillsorchardridge.com).
From there, catch US-61 north, heading past steep ravines and rolling meadows to Viroqua, where the Driftless Cafe (driftlesscafe.com) serves seasonal meals like trout with roasted root veggies made with local, sustainable ingredients. Or drive back to La Crosse for an elegant meal of seared Hawaiian snapper and citrus-glazed beet salad at The Waterfront Restaurant and Tavern (thewaterfrontlacrosse.com).
Across the river in La Crescent, Minnesota, get on the Hiawatha Apple Blossom Drive Scenic Byway (lacrescentmn.com). At the drive’s northern end, some of the state’s prettiest hiking trails thread the ridges at Great River Bluffs State Park (dnr.state.mn.us/state_parks). Byway markers are scant, but even if you make a wrong turn, you’ll find yourself pleasantly lost among pastoral views.