Backroads to Lacona and Milo: quiet barns and a pie stop near Osceola

A late afternoon drive on county roads north of Osceola can feel like stepping into a postcard. You roll past corn stubble, weathered red barns, gravel lanes, and windbreaks of old cottonwood.

When you are at The Jeffreys for an extended stay or just passing through the area, the plan is simple. Leave Osceola, wander toward Lacona and Milo in Warren County, grab something warm to eat, and wrap the night by the water. Lacona sits about a half hour from Osceola by car if you take the back way instead of the highway, and Milo is just up the road from there. This loop is calm, easy, and perfect for golden hour photos.

Stop 1. Barn hunting outside Lacona

Point your car northeast out of Osceola and ease into farm country. Keep an eye out for classic red barns with white trim, metal grain bins lined up like silver domes, and the painted quilt panels you sometimes see mounted high on a barn face. Barn quilts started as big painted wood squares, patterned like fabric quilts, and they’ve become a rural art project across Iowa to honor farm families and local history. If you’re driving with kids, give them a game. First one to spot a barn quilt picks the next music. No barn quilt in view yet. Cool. Switch to “count the wind turbines” or “how many round bales on that hill.”

Pull offs: look for long gravel drive approaches with good sightlines, not blind hills. Do not stop on a curve. You want a flat shoulder where you can get all four tires clear of the lane. Shoot barns at an angle, not straight on. That gives you depth, plus sky.

If you see a farmer outside, wave. This is still someone’s work site, not an exhibit. Stay on the public right of way.

Stop 2. Milo’s octagon barn

North and a little east toward Milo, you’re in old horse and dairy country. One standout is the historic octagon barn near Milo in rural Warren County. It was built around 1900 as a working barn and it’s on the National Register of Historic Places. The shape looks almost like a red stop sign with a roof. It’s one of those “pull over right now” moments. You do not see many eight sided barns anymore.

This is a good place to practice low shots. Park well off the road on a straight stretch. Kneel or sit and get some of the gravel in the foreground. That texture makes the barn pop in photos without needing any fancy filter.

You can also grab a quick family shot here. Barn behind you. Sun behind the barn. Everyone faces the camera in soft light. Done.

Stop 3. Small town supper in Milo or Lacona

By now it is early evening, and you probably want food. Milo is tiny and friendly, around 800 people, and has a true small town “you’re welcome here” sit down feel. Houston’s on Main in Milo is the classic stop. It’s right on Main Street and leans hard into hometown comfort, pizza, grill plates, and a relaxed bar vibe. Ask what the special is and if they’ve got pie or dessert left. You’re not here for fancy. You’re here for something hot, a refill on coffee, and to thaw out your hands.

If you’d rather end up in Lacona, you can land at a bar and grill style spot and do the same thing. Warren County tourism lists local one off places like Backroads Bar & Grill in Lacona, the kind of spot where dinner is still “supper” and the conversation is local football, harvest, and road conditions. Get whatever sounds like it came off a flat top. Bonus points if they still have homemade pie by the slice. Ask before you sit down so you can call dibs.

Tip: call ahead if you’re running late. Kitchens in small towns sometimes close earlier than the bar.

Stop 4. Bridge and water light

After supper, point the car north toward Lake Ahquabi State Park, south of Indianola. The park sits on a 115 acre lake and dates back to the 1930s, when crews built stone shelters and a lodge that still carry that old CCC look. On calm evenings, the lake throws back deep orange and pink. You can pull off near the causeway or main lot and catch the reflection line across the water. Keep headlights off while someone’s shooting, but leave hazard flashers on if you’re on the shoulder and not in a marked lot.

This is also a nice place to stretch legs before heading back to Osceola. Walk down to the shoreline, breathe in the cold air, and listen. You’ll usually hear geese first, then frogs or crickets if it’s warm, and sometimes nothing at all if it’s winter quiet.

How to make it kid friendly

Make it a scavenger run, not a lecture. Tell them you’re trying to find three things and you’ll take a picture of each one.

1. A barn with peeling red paint.
2. A quilt square on a barn.
3. Water at sunset.

Let them “direct” one shot. Hand them your phone and let them pick the angle. You will get low fence lines, dashboard reflections, maybe a blurry selfie in a car window. Keep those. That’s the trip.

Safety and courtesy

Most of these roads are two lane blacktop or gravel. Visibility can drop fast at dusk. Run your lights. Pull fully off on straight stretches. Do not block a field drive. Watch for deer, loose cattle, and farm equipment after dark. Locals use these roads every day to get home.

If you get turned around, no stress. You’re never more than about a half hour from Osceola, and most of these little towns sit within 30 to 35 minutes north and northeast of town by normal driving. Worst case, head south and follow signs back to Highway 34 or I-35.

In Conclusion

This loop gives you old barns, wide sky, a real local meal, and a soft sunset on the lake, all without leaving south central Iowa. It is easy to shoot, easy to repeat, and different every season. In fall you get gold bean stubble and orange light. In winter you get blue shadows and frost on fence lines. In spring you get dark tilled rows and geese on open water.

If you love a slow Iowa drive, you might also like our Quiet Roads and Barns loop for more photo stops near Osceola. For outdoor time closer to town, check out Trails and Lakes Near Osceola or plan an easy sunrise walk from Daybreak at East Lake Park. Need a cozy stay after your road trip? Our 48 Hours in Osceola blog has you covered with warm meals and local tips that make every mile feel like home.