Madison County Fall Crawl
Sunday, September 27, 2026
Covered Bridges Winery
2207 170th Trail
Winterset | Map It Capital Country Website
Email
5157299463 5157299463
2207 170th Trail
Winterset | Map It Capital Country Website
5157299463 5157299463
The Madison County Fall Crawl is a small, local event near Winterset, IA that takes place on the last Sunday in September. Take a drive with friends around Madison County to see 15 small local businesses in their rural setting. There are a few stops along the crawl that have normal business hours where you can grab a glass of coffee, wine, cider, beer, or a bite to eat. The fall crawl is a free event for the entire family, with lots of fun things to do with live music, kid's activities, 80+ vendors and food trucks. Earliest businesses opening at 9am. Varies by stop location. Covered Bridges Winery will have live music from 1-4PM by Looking 4 Luke. Looking 4 Luke is an energetic cover trio performing a wide variety of genres and musical generations with a decidedly unplugged feel.