7 Most Scenic Drives in Missouri

Take the backroads in Missouri and you’ll see more than trees and fields. These scenic drives pass through river country, old mill towns, vineyards, and stretches of the Ozarks and Mississippi bluffs that you can’t see from the highway. Each of its seven most scenic drives can be done in just a few hours, starting and ending in a small town, with plenty of spots to pull over and explore along the way.

Hermann Wine Country Loop

Imagine a road that feels less like a highway and more like a trip back in time. That’s the Hermann wine country loop — a short, scenic route that winds through Missouri’s version of the Rhineland. It’s especially striking with vineyard colors in fall or wildflowers in the spring. The route begins in Hermann, a town founded by German settlers in 1837, where brick storefronts, river bluffs, and quiet streets set the tone.

The drive passes six family-owned vineyards that produce nearly a third of the state’s wine. Sip wine at Stone Hill, where limestone cellars date back to the 1800s and award-winning Norton reds wait to be savored. Wander into Hermannhof or Adam Puchta, tasting blends that grew out of German tradition and Missouri soil. Break the drive with a stop at Grand Bluffs, just minutes away, with 300-feet-high bluffs overlooking the river valley below. Back in Hermann, visitors can browse art galleries, local shops, or the historic Deutschheim State Historic Site, where German immigrant life is preserved in homes, tools, and even a working vineyard.

Arrow Rock to Boonville

The Arrow Rock to Boonville drive blends scenery with history at every turn. It starts in Arrow Rock, a small village that sits high on limestone bluffs above the Missouri River. The town is a National Historic Landmark, known for the old J. Huston Tavern, which still serves meals as it did in 1834, the Lyceum Theatre, and the restored home of painter George Caleb Bingham. With its Santa Fe Trail ties, the village feels less like a museum and more like a pioneer settlement waiting for wagons to roll in.

The road continues to Boonville, once a bustling river port and the site of Civil War skirmishes. On the way, the Katy Trail State Park offers a chance to walk or bike along the river. In Boonville, you can stroll the cobblestone street that once carried goods from steamboats, hunt for antiques, tour historic mansions, or visit the Mitchell Antique Motorcar Museum. Whether crossing the bridge over the Missouri or relaxing in the riverside park, this short drive packs history, scenery, and small-town charm into just a couple of hours.

Ste. Genevieve to Kimmswick

The Ste. Genevieve to Kimmswick route follows the Mississippi through two of Missouri’s most historic towns. Starting in Ste. Genevieve, the state’s oldest European settlement, the streets lined with French Colonial homes, stone cottages, and landmarks like the Louis Bolduc House and Felix Vallé House, are now preserved as part of a National Historical Park. The town’s French influence shapes its culture, from preserved architecture to local traditions, making it a rare glimpse into 18th-century frontier life.

Heading north, the road follows the river to Kimmswick, a mid-19th-century town that feels like you are walking through a living museum. Restored brick storefronts hold shops and cafés, and the Blue Owl Bakery draws visitors for its famous “Levee High Apple Pie.” The Anheuser Estate offers a look into the home and history of the brewing family, while nearby Mastodon State Historic Site adds a prehistoric twist with fossils and exhibits. In spring, blossoms brighten the route; in fall, the river bluffs burn with color, making this 2.5- to 3-hour drive as much about the journey as the destinations.

Weston to Parkville Countryside Drive

The Weston to Parkville countryside drive is the kind of trip where the scenery feels familiar yet full of surprises. Stretching about 25 miles, the route starts in Weston, a historic river town once central to Missouri’s frontier trade. Today, its brick storefronts, antique shops, and stops like Pirtle Winery and Holladay Distillery give it an old-world character that’s easy to linger in. Just outside town, Weston Bend State Park delivers sweeping views of the Missouri River and wooded trails that turn brilliant with color in the fall.

From there, the road winds south through rolling farmland before reaching Parkville, another riverside gem. Downtown Parkville mixes antique shops, cafés, and galleries with a relaxed small-town pace. The riverfront parks, English Landing and Platte Landing, offer the perfect place for quiet walks and picnics. In contrast, the Parkville Nature Sanctuary offers forest trails and wildlife sightings only minutes from Main Street. It’s a short drive that ties together countryside calm, historic flavor, and seasonal beauty, making it one of Missouri’s most rewarding day trips.

Eminence Ozark National Scenic Riverways Loop

The Eminence loop is a winding 75-mile route that captures the wild heart of the Missouri Ozarks in about 3 hours. Starting in Eminence, you’re right at the gateway to the Ozark National Scenic Riverways, which was the nation’s first “scenic riverways.” The Jacks Fork and Current Rivers run clear and fast here, perfect for kayaking, tubing, or simply enjoying from the riverside.

The loop carries you through deep forests, over ridges, and into valleys dotted with natural springs and caves. Stops include Alley Spring with its striking red mill and turquoise waters, and Blue Spring, one of the deepest in the U.S. Wildlife sightings are common along the quiet backroads, from wild turkey to deer. Take a short detour to Rocky Falls Shut-Ins, a natural cascade perfect for photos. In summer, the rivers are alive with float trips, while fall paints the hillsides gold and crimson, making every bend in the road feel like a postcard. By the time you return to Eminence, the mix of rivers, history, and rugged Ozark beauty makes the loop feel both refreshing and timeless.

Steelville to Caledonia

The Steelville to Caledonia scenic drive stretches for about 50 miles along a route that links river valleys, forested hills, and historic Ozark towns. It begins in Steelville, known as the “Floating Capital of Missouri,” near where the Meramec, Huzzah, and the Courtois rivers flow. Downtown Steelville has murals, old storefronts, and small diners that remind you why this corner of Missouri has long been a base for paddlers and anglers. Plus, you can also explore the underground wonders in the Onondaga Cave State Park.

The drive north winds through thick woods and open farmland dotted with old mills and creek crossings. A highlight is Dillard Mill State Historic Site, where a red 1908 gristmill sits against Huzzah Creek, offering trails and picnic spots. By the time you reach Caledonia, you’ve traded river culture for frontier history. Founded in the early 1800s, the town is one of Missouri’s oldest historic districts, with antique shops, a vintage mercantile, and preserved architecture that speaks to its Scottish heritage. In spring, dogwoods bloom along the route, and in autumn, the hills blaze with reds and golds, making this byway one of Missouri’s most rewarding seasonal drives.

Cape Girardeau to Perryville

The Cape Girardeau to Perryville river drive is a winding journey along the Mississippi where limestone bluffs, farmland, and river towns highlight the character of southeast Missouri. Starting in Cape Girardeau, you’ll find a lively historic riverfront lined with the Mississippi River Tales mural that stretches for blocks, each one telling a piece of Missouri’s story. Landmarks like the 1890 Glenn House, Old St. Vincent’s Church, and the Red House Interpretive Center connect the present to the city’s early frontier days, while Trail of Tears State Park north of town offers striking views of the Mississippi River from its high bluffs.

From there, the road follows a rolling landscape of fields and forests toward Perryville, a town with French colonial roots. Stops along the way can include quiet river overlooks, small communities, and stretches of the Great River Road. In Perryville, you can explore the National Shrine of Our Lady of the Miraculous Medal, wander downtown antique shops, or relax at the city park with its lake and walking paths. In spring, wildflowers brighten the roadside, while autumn turns the bluffs and farmland into a palette of deep reds and golds. At 85 miles and lasting about 2.5 hours to 3 hours, this drive is a longer one, but the mix of history, river views, and small-town stops makes it worth the time.

Missouri’s backroads show a side of the state you won’t find on the interstate. Each of these short drives links history, small towns, and natural beauty into a few easy hours behind the wheel. Whether you’re trading the river bluffs near Hermann, rolling through Ozark forests, or walking cobblestone streets in old river towns, the routes offer more than scenery. They’re a reminder that Missouri’s culture and landscapes are best experienced at a slower pace, with time to stop, look around, and take it all in.