Madison County Fall Crawl

The Madison County Fall Crawl is a small, local event near Winterset, IA that takes place on the last Sunday in September, the 29th in 2024. 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, 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 55+ vendors. Earliest businesses opening at 8 a.m. Varies by stop location. If you love Madison County as much as we do, you probably already know how excited we are for the 4th year! We’re so pumped for this event to kick off! We have more live music, more food, more fun and it’s all free to attend! Flowers, coffee, local meats, wines, brews, food, niche vendors, food trucks, free samples, kids games, and more! You won’t go hungry this year! New fall crawl tshirts & sweatshirts this year! If you dont know where to start, there are many options! Pammel Park Coffee Co (open at 8) will have fresh coffee & lattes, breakfast noms, The Drift (open at 9) is serving up brunch, PepperHarrow (open at 9) & Iris Aisle (open at noon) are hosting coffee trucks The Bean Iowa & Vintage Road Coffee Co and Cedar Shake Farm will have the famous Corndog Caravan serving up Breakfast Corndogs as well as other homemade breakfast treats! A host of food trucks & food vendors to check out at each location! Fall Crawl swag available!!