A Quick Guide to the Madison County Covered Bridge Festival
For one weekend each October, downtown Winterset gets very busy. Vendors fill the streets around the courthouse, live music plays nearby and visitors head out across Madison County to see the covered bridges.
The 2026 Madison County Covered Bridge Festival is set for Saturday, October 10, and Sunday, October 11. Most of the action is around the courthouse square, but some of the best festival activities are a short drive away.
Here are the highlights.
Quick details
- Dates: Saturday, October 10, and Sunday, October 11, 2026
- Main location: The Madison County Courthouse square in downtown Winterset
- Admission: To be announced
- Schedule and entertainment lineup: To be announced
- Pet policy: Only service animals are allowed inside the festival grounds
- Smoking: Not allowed inside the festival grounds
- Official website: Madison County Covered Bridge Festival
Start with a walk around the square
If this is your first visit, start at the courthouse square. It is the heart of the festival and the easiest place to get a feel for everything happening that weekend.
The surrounding streets are lined with booths selling handmade items, artwork, crafts, food and plenty of other finds. Take a lap before settling on lunch or making your first purchase. There is a lot packed into a few blocks, plus the shops around the square are open and easy to reach on foot.
Let someone else handle the covered bridge route
Madison County has six remaining covered bridges: Cedar, Cutler-Donahoe, Hogback, Holliwell, Imes and Roseman. You can certainly visit them on your own, but festival weekend brings extra traffic to Winterset and several bridges require travel on gravel roads.
That is what makes the guided tours from the Winterset Rotary Club worth considering. Previous festival tours have stopped at Roseman, Hogback and Cutler-Donahoe bridges, along with the North River Schoolhouse. A guide handles the route and shares stories along the way.
Routes, prices and departure times may change for 2026. Tickets are typically sold at the Rotary booth on the festival grounds, so check the final details before arriving.
Short on time? Cutler-Donahoe Covered Bridge is inside Winterset City Park and is the easiest one to pair with the downtown festival.
Save time for the Madison County Historical Complex
This part of the festival is easy to overlook because it is not on the courthouse square, but it deserves a stop.
Madison County Historical Complex
815 S. Second Avenue, Winterset
Activities traditionally include:
- Free museum admission
- Horse-drawn wagon rides
- Penny candy at the Field Mercantile
- Tours of the Bevington Mansion
- Civil War reenactments and demonstrations
- A Saturday evening cannon firing
- Free s’mores and popcorn
The complex also offers free parking.
Bringing the kids?
Look for the Kids Zone on West Jefferson Street between First and Second avenues. More activities are available indoors at the Warehouse on 2nd, which could be especially useful if the October weather does not cooperate. Kids Zone activities are included with festival admission.
Stop for the live entertainment
Music and other performances run throughout both days on the south side of the courthouse. There is no extra charge beyond festival admission, so it is easy to catch part of a performance while you are exploring the square. The 2026 lineup will be announced closer to the event.
Find a spot for the parade
The parade is one of the busiest parts of the weekend. Expect antique vehicles, community groups and festival royalty making their way through Winterset. Arrive early if you want a good view, especially around the courthouse square.
Visit Sunday for the car show
The 40th Annual Madison County Car Show is scheduled for Sunday, October 11, 2026, from 8 a.m. to 3 p.m. near the courthouse square. Vehicle registration ends at noon, with awards presented at 3 p.m.
The listed $20 fee is for people entering a vehicle in the show. It is not a spectator admission charge.
A few things to know before you go
- Arrive early. Downtown parking becomes harder to find as the day goes on.
- Wear comfortable shoes. You will cover more ground than you might expect.
- Bring layers. October weather in Iowa can change quickly.
- Carry some cash in case a vendor does not accept cards.
- Leave pets at home unless they are service animals.
- Check the official schedule shortly before leaving home. Several 2026 details are still being finalized.
