Events & Things To Do In Winterset This Weekend | October 17-19, 2025| AllEvents

Live Music at Winterset Cidery

Date and Time: Sat, 18 Oct, 2025 - 05:00 PM
Location: 1638 Highway 169, Winterset, IA, United States

Saturday at the Cidery! Join us for a full day of fun: • Good & Golden Permanent Jewelry | 12–5pm • The Brick’n Bob Duo live music | 5–8pm • Madison County Cattlemen serving dinner | 5–8pm Come early, stay late, and enjoy an amazing day with us at... Read More

Lean Into The Light: New Watercolors By Christine Hilbert

Date and Time: Sat, 18 Oct, 2025 - 01:00 PM
Location: The Warehouse on 2nd, 231 N 2nd Ave,Winterset, Iowa, United States

Come celebrate the unveiling of Christine Hilbert's latest watercolor series, Lean Into The Light from 1-7pm on Saturday October 18, 2025 at The Warehouse on 2nd. Artist Reception will take place from 5-7pm with music by DJ All Day. Christine Hilbert’s L... Read More

Willie Mac & The Lost Cousins / Music at the Winery

Date and Time: Sat, 18 Oct, 2025 - 06:30 PM
Location: Covered Bridges Winery, 2207 170th Trl, Winterset, IA 50273-8200, United States

$5 Cover Charge Per Person Live Music from 6:30-9:30PM Gluten Free Steils Food Truck serving from 5:00-8:00PM Music will be outdoor weather permitting. Willie Mac and the band will perform an infusion of bluegrass, folk-rock and blues.... Read More