Five Iowa counties, one road, and a slice of the 1800s that never left

Southeast Iowa’s best-kept 105-mile drive

Southeast Iowa doesn’t show up on many road trip lists, and that’s exactly the point.

The Historic Hills Scenic Byway runs about 105 miles through five counties where horse-drawn buggies share the road with your car, steamboat towns sit largely unchanged from the 1800s, and a little white house launched one of the most famous paintings in American art history.

You can drive the whole thing in a day, but you won’t want to.

Rolling hills, five counties and zero fast food

The byway threads through Wapello, Appanoose, Davis, Van Buren and Lee counties, passing about 20 small towns on its way southeast. Rolling hills give way to thick forest, then open onto farm ponds and river bottomland.

The road was once signed as the Woodlands Scenic Byway, and western branches push out toward Blakesburg and Moravia. You won’t find a single fast-food chain along the whole route.

Pack a cooler or plan to eat where locals eat, because the options are small and the kitchens close early.

Steamboats once docked where cows now graze

The towns along this drive are some of the oldest-settled land in Iowa, with roots going back to the 1830s.

By the mid-1800s, steamboats worked the Des Moines River, stopping at little ports that are now quiet crossroads.

Mormon pioneers crossed the river here at Ely’s Ford on their push west, a route now marked as the Mormon Pioneer Trail.

Amish and Mennonite families eventually settled into the hills near Bloomfield and Drakesville, and their communities have kept traditional ways intact ever since.

Slow down for the horse and buggy ahead

Around Bloomfield and Drakesville, you’ll come up behind an Old Order Amish buggy on a two-lane road, and it’s worth slowing down and staying there for a while.

More than 100 Amish and Mennonite family businesses operate in this area, many of them open to visitors. You can buy handmade furniture, fresh-baked goods, quilts and fabric directly from the families who made them.

The pace here doesn’t rush for anyone. The hills roll by at horse speed, and after 20 minutes of it, you’ll stop noticing the time.

Prairie Breeze cheddar is worth the detour to Milton

A Mennonite family opened Milton Creamery in the small town of Milton back in 2006, sourcing milk from Amish and Mennonite dairy farms just a few miles away.

Their flagship cheese, Prairie Breeze, is a white cheddar aged at least nine months. It has a sweet, nutty flavor with a slight crunch from the natural crystals that form as it ages.

The cheddar has picked up national and international awards. Pick some up here, because you’re not likely to find it at your regular grocery store back home.

Thirteen miles of trails through oak bluffs and river bends

Lacey-Keosauqua State Park covers about 1,650 acres where the Des Moines River bends hard to the south.

Iowa’s second-oldest state park, dedicated in the early 1920s, it has about 13 miles of trails working through oak and hickory bluffs above river valleys.

The Civilian Conservation Corps built many of the park’s stone and timber structures in the 1930s, and they’ve held up well.

There’s a lake for swimming and fishing, plus cabins and campsites if you want to stay the night and start the next section of the drive in the morning.

Ancient burial mounds watch over the Des Moines River

Walk to the northwest corner of Lacey-Keosauqua and you’ll find 19 ancient American Indian burial mounds on a wooded ridge above the river. The Woodland Culture people built them centuries ago.

A quiet trail runs past each one, close enough to see but laid out to give the mounds their space. The river bends below, the same water that’s been running past this ridge the whole time.

It’s one of those spots on the drive where you stop looking for things to do and just stand still for a minute.

Bentonsport still looks like an 1800s river port

Bentonsport is a National Historic District, and the designation fits.

The village was a busy steamboat port on the Des Moines River more than a century ago, and it hasn’t changed much since the boats stopped coming.

A century-old iron truss bridge now crosses the river as a footbridge.

Working artisans, potters, blacksmiths, quilters and sculptors, still occupy the old buildings along the water. Where a mill once stood, a community rose garden now blooms.

Walk the main street slowly. The whole village takes about 20 minutes, but the details reward a closer look.

The courthouse that’s been open since 1843

The Van Buren County Courthouse in Keosauqua went up in 1843, making it the oldest courthouse in continuous use in Iowa and the second-oldest in the country.

Built in the Greek Revival style, its brick walls run up to 22 inches thick. Local oak frames the structure inside, and native walnut woodwork runs through the interior.

The second-floor courtroom still handles real cases today. During business hours, you can walk in and see it.

Most people drive past it without realizing what it is.

Stand where Grant Wood set up his famous painting

The small white house in Eldon is where Grant Wood stood in 1930 when he sketched the background for “American Gothic.”

The house itself dates to the 1880s, built in the Carpenter Gothic style with the pointed upstairs window that made it into the painting.

A shape cut into the sidewalk shows you exactly where to plant your feet for the matching photo. The visitor center has props, the pitchfork included, so you can pose like the two figures in the painting.

Admission is $5 for adults 13 to 59, $4 for visitors 60 and older, and free for children 12 and under.

Lake Wapello’s sand beach and CCC-era cabins

Lake Wapello State Park takes up about 1,150 acres of wooded hills in southern Iowa, and it has one of the better sand beaches in the region if you want to swim.

Thirteen cedar-sided cabins sit near the water, several of them built during the CCC era. A stone-and-timber beach lodge from the 1930s overlooks the lake.

About seven miles of trails loop through the surrounding woods along the shoreline. If you want to stay more than a day on this drive, the park gives you a real reason to.

Paddle the river or hike through Shimek State Forest

Shimek State Forest near Farmington is one of Iowa’s largest, with miles of trails used by hikers and horseback riders.

The Des Moines River Water Trail has 10 access points along this stretch, so you can put in a canoe or kayak at one point and pull out at another.

Anglers fish for bluegill, crappie, catfish and bass in the lakes and river. Songbirds fill the forest in spring, and wildlife moves through the trees year-round.

Near Moravia, the byway also passes Iowa’s only resort state park, sitting beside a large lake with lodge rooms, cabins and trails.

Drive the Historic Hills Scenic Byway in Iowa

The byway runs about 105 miles through southeast Iowa with no entrance fee for the route itself. State parks along the way may charge for camping or cabins.

Look for the Historic Hills wayfinding signs to stay on course, and download a byway map through the Iowa Byways or Travel Iowa websites before you leave. The road is mostly paved with one short gravel stretch.

Late spring through fall works best for open historic sites, river activities and state park facilities. Some village shops keep limited hours, so call ahead if you have a specific stop in mind.

This article was created with AI assistance and human editing.

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