Winterset, IA

The county's oldest family-owned eatery, an old-fashioned soda fountain with swivel stools right on the courthouse square. Order a hand-dipped chocolate shake with the house-made cola; it doubles as a working pharmacy and gift shop.

A family-run Mexican spot in a historic two-storefront building on the square, with fresh chips and salsa and enormous portions. Ranked among the town's top restaurants, it is a share-an-entree kind of place.

A tiny craft-coffee and small-batch-baked-goods spot a block off the square, the locals' top-rated breakfast and light-lunch stop. Grab a pastry and espresso before doing the covered-bridge loop.

A made-from-scratch bakery a block off the courthouse square with daily-batch donuts, breads, and seasonal pastries. Opens early Tuesday through Saturday; the apple fritter and glazed items sell out well before noon.

A pastry, pie, and sweet shop on the south side of the square that also serves homemade soups and made-to-order paninis at midday. Come for pie and a panini at lunch, not dinner.

An old-school walk-up ice cream stand a couple of blocks from the square, with hard-dip and soft serve and a nostalgic small-town feel. The classic after-dinner ice cream stop.

A wooded city park with trails, the Cutler-Donahoe covered bridge, Clark Tower, a hedge maze, and limestone bluffs, all walkable from downtown. A great low-effort alternative to the rural bridge loop.

An easy loop through the city park to the limestone Clark Tower, passing the covered bridge and the hedge maze along the way. The trail shares the park road with cars and has no sidewalk, so stay alert.

A short, scenic out-and-back along the limestone backbone ridge in Pammel State Park, with elevated views of the Middle River and a historic road tunnel carved through the ridge. Drive through the one-lane tunnel, then hike the ridge above it.

A self-guided driving loop linking all six historic covered bridges through Madison County's rolling farmland. Pick up the free map at the welcome center and plan a few hours; some bridges end on gravel, so skip it after heavy rain.

A multi-building living-history complex on the edge of town, anchored by a limestone mansion and including a depot, schoolhouse, church, and a barn of antique farm machinery. The Victorian-furnished mansion is the crown jewel.

A lovingly restored single-screen historic cinema and performance space a block off the square, showing first-run films plus classics, with famously good popcorn. Catch a midweek classic screening for the full vintage-marquee experience.

An estate winery on the rolling hills near St. Charles, with vineyards surrounding the tasting room, wine slushies, oven-fired pizzas, and an on-site brewery. The dog-friendly outdoor seating with hill views is the draw in good weather.

A family-owned boutique winery on a ridge with one of the best views in the state, pouring award-winning reds and whites, wine slushies, and hosting summer outdoor music with food trucks. The fireplace-and-sofa tasting room is open year-round.

The restored four-room house where the actor was born, paired with a sizable museum of film memorabilia, costumes, scripts, and his last custom car. The house tour next door is the highlight; admission covers both.

The most famous of the county's six covered bridges, a lattice-truss span that featured heavily in The Bridges of Madison County. Visitors still tuck handwritten notes into the interior beams, a tradition from the film.

A covered bridge relocated into Winterset City Park, the easiest of the six to reach on paved access and walkable right in town. Combine it with the Clark Tower hike rather than driving the rural loop.

A Second Empire limestone courthouse anchoring the historic Winterset square, ringed by cafes and shops. The square around it is the best photo and people-watching spot in town.

A quilt museum in a historic former department store on the south side of the square, with rotating exhibits of vintage and contemporary American quilts a few times a year. Worth a stop even on a repeat visit, since the shows change.

A castle-like three-story limestone tower overlooking the Middle River valley in Winterset City Park, built as a memorial to early settlers. Drive up the narrow park road or hike to it, then climb the exterior stone steps for the valley view.