seasonal guide

A Fall Covered-Bridge Day in Madison County: Historic Spans, a Stone Tower, and Old-School Treats

Autumn in Iowa brings crisp air, brilliant gold and crimson leaves, and the perfect excuse for a scenic drive. While Madison County is famous for its collection of historic covered bridges, trying to rush through all six in one day can turn a fun outing into an exhausting chore. This relaxing day-trip itinerary is designed for families, couples, and photographers who want to appreciate the county’s famous landmarks at a comfortable pace. You will explore two of the most iconic rural bridges, enjoy an authentic 1920s soda fountain lunch on the historic Winterset square, navigate a stone maze, and climb a medieval-style tower for panoramic views of the colorful Middle River Valley.

At a glance

Trip type: Seasonal Guide (Autumn)
Best for: Families with teenagers, couples, and photographers
Area or route: Madison County (Winterset, Hogback, and Roseman bridges)
Time needed: 6 hours
Best season: Late September through October (for peak fall foliage)
Estimated budget: $15–$25 per person for lunch and treats
Total driving: Approximately 25 miles (excluding travel to and from Madison County)
Accessibility notes: Most bridge viewing areas are grassy and gravel-covered. Winterset City Park and the Courthouse Square feature paved sidewalks. The road to Clark Tower is unpaved and narrow, and the tower itself requires climbing stone stairs.
Reservations: None required
Last verified: July 16, 2026

The itinerary

Time	Stop	Plan
10:00 a.m.	Hogback Covered Bridge	Explore a valley bridge and sign the guest log
10:50 a.m.	Roseman Covered Bridge	Visit the county's most famous and legendary span
11:35 a.m.	Montross Pharmacy Soda Fountain	Lunch at a classic 1920s counter on the town square
12:50 p.m.	Winterset City Park & Clark Tower	Walk a city park bridge, solve a maze, and climb a stone tower
2:35 p.m.	Frostee's	Grab soft-serve treats at a seasonal walk-up stand

Stop 1: Hogback Covered Bridge

Your autumn adventure begins just north of Winterset at the Hogback Covered Bridge. Built in 1884 and named after the nearby limestone ridge, this 97-foot structure sits in a quiet, rural valley surrounded by timber that bursts into bright yellow and orange hues each October. Because it is located at the end of a scenic gravel road, it feels like a step back in time.

Walk inside to admire the historic timber construction, feel the cool autumn breeze passing through the open windows, and sign your name in the guest journal kept in a mailbox inside the bridge. It is an ideal spot to take your first photos of the day, as the bridge is framed beautifully by the surrounding forest.

Address: 1875 Hogback Bridge Rd, Winterset, IA 50273
What to do: Walk through the bridge, sign the guest book, and take photos from the grassy banks.
How long to allow: 30 minutes
Practical advice: The last mile of the drive is on a gravel road. Drive slowly to minimize dust, and watch for farm equipment.

Stop 2: Roseman Covered Bridge

Next, head southwest toward the Roseman Covered Bridge, arguably the most famous span in the county. Constructed in 1883, this bridge gained international fame as a key setting in both the novel and film The Bridges of Madison County.

Beyond its Hollywood connection, the bridge is famous for a local legend. In 1892, an escaped county jail prisoner supposedly ran inside the bridge, found himself surrounded by a posse on both sides, rose through the roof with a wild shout, and vanished—leading locals to call it the "Haunted Bridge." Today, the red bridge sits peacefully over the Middle River. Take a stroll along the bank to appreciate the architecture and enjoy the gentle sound of the river flowing underneath the autumn canopy.

Address: 2450 Roseman Bridge Rd, Winterset, IA 50273
What to do: Explore the bridge exterior, walk down to the river bank, and browse the small seasonal souvenir shop next to the bridge if open.
How long to allow: 30 minutes
Practical advice: The approach to Roseman is also gravel and can be dusty or bumpy. Parking is available in a small dirt lot near the bridge.

Stop 3: Montross Pharmacy Soda Fountain

After exploring the rural bridges, drive back to the center of Winterset for lunch. Park your car near the historic Madison County Courthouse and walk to Montross Pharmacy. While it looks like a typical independent pharmacy from the outside, the back of the store houses "The Fountain," a classic lunch counter that has been serving hungry locals since 1921.

Slide onto a vinyl stool or slip into a wooden booth to order a classic Iowa lunch. The menu features simple, delicious staples like homemade pork tenderloin sandwiches, hamburgers, and crinkle-cut fries. Don't leave without ordering an old-fashioned soda, cherry Coke, or a thick malt mixed right behind the counter using vintage equipment. The friendly, bustling atmosphere is a wonderful slice of small-town Iowa life.

Address: 118-120 N 1st Ave, Winterset, IA 50273
What to do: Enjoy a classic lunch and order an old-fashioned soda fountain malt or shake.
How long to allow: 1 hour and 10 minutes
Practical advice: The lunch counter is closed on Sundays. Peak lunch hours on Saturday can be busy, so arriving slightly before noon helps you beat the crowd.

Stop 4: Winterset City Park and Clark Tower

After lunch, take a short five-minute drive south to Winterset City Park. This expansive park is packed with historic features that make it a highlight of the trip. Near the park entrance, you will cross the Cutler-Donahoe Covered Bridge, built in 1870 and moved to the park in 1970. This paved stop is highly accessible and perfect for a quick look.

Next, make your way to the English Hedge Maze, a circular labyrinth of dense shrubs that is fun for teenagers and children to navigate.

Finally, follow the narrow, one-way dirt road that winds upward through the woods to Clark Tower. Built in 1926 out of native limestone to honor the county’s early pioneers, this medieval-style tower stands 25 feet tall. Climb the interior stone steps to the top deck for a breathtaking, unobstructed view of the Middle River Valley, where the autumn leaves stretch across the hillsides like a colorful patchwork quilt.

Address: 1006 S 9th St, Winterset, IA 50273
What to do: Walk through the Cutler-Donahoe Bridge, navigate the hedge maze, and climb Clark Tower.
How long to allow: 1 hour and 40 minutes
Practical advice: The road to Clark Tower is a narrow, one-way dirt road. Large vehicles (like RVs or trailers) should not attempt it. The road is closed seasonally from mid-November to April and closes daily at sunset.

Stop 5: Frostee's

End your afternoon on a sweet note at Frostee's, a beloved local walk-up ice cream stand located just off the courthouse square. Operating seasonally from spring through autumn, this retro spot is the perfect place to sit outside and reflect on your day.

Order a classic soft-serve cone, a sundae, or a specialty shake from the walk-up window. Grab a seat at one of the outdoor picnic tables and enjoy the crisp fall afternoon as you enjoy your treat.

Address: 101 E Green St, Winterset, IA 50273
What to do: Grab soft-serve ice cream, malts, or a shake at a historic walk-up stand.
How long to allow: 40 minutes
Practical advice: Frostee's is a seasonal business that closes for the winter, usually in late October or early November. Seating is entirely outdoors.

Map and driving order

Your route starts north of Winterset, loops west, and finishes in the town center:

Hogback Covered Bridge (Start)
Roseman Covered Bridge (Drive 20 minutes southwest via gravel roads)
Montross Pharmacy (Drive 15 minutes east to the Winterset square)
Winterset City Park (Drive 5 minutes south from the square)
Frostee's (Drive 5 minutes north back to the square)

Total active driving time between stops is roughly 45 minutes, covering approximately 25 miles.

Before you go

Road and Weather Preparedness: Several stops on this route are on gravel roads or dirt paths. In wet weather, these roads can be muddy. Verify local park road conditions by contacting Winterset Parks and Recreation at 515-462-3258.
Footwear: Comfortable closed-toe walking shoes are highly recommended for walking around the bridges, navigating the maze, and climbing the stone tower.
Rainy-Day / Late Fall Backup: If the weather turns cold or wet, swap the outdoor bridge walks for a visit to the Iowa Quilt Museum or the John Wayne Birthplace & Museum, both located right on the Winterset courthouse square. You can also swap Frostee's for warm drinks and baked treats inside Petite Cafe (106 W Court Ave, Winterset, IA).

Plan another Iowa adventure

Ready to explore somewhere new? Find more day trips, weekend ideas, and memorable local stops in our Iowa travel guides.