Winterset Wine Walk
May 9, 2026
Join the Madison County Chamber of Commerce, downtown Winterset merchants, and area wineries for shopping, wine sampling, music, and more!
Paint Madison County (A Plein Air Festival)
June 13-14, 2026
The Madison County Chamber is excited to invite artists to apply for Paint Madison County, a community art event celebrating creativity, place, and talent. We want to see how you interpret Madison County.
This event brings together artists and the public to experience our county through art, storytelling, and inspiration. Artists will have the opportunity to showcase their work, connect with the community, and be part of a vibrant, creative experience.
Annual Chamber of Commerce Golf Outing
June 22, 2026
Gather your team of four and come enjoy a morning of fun, fresh air, and networking with your fellow chamber members at Lakeview Golf & Country Club in Winterset. Registration is at 8:00 am, and shotgun starts at 9:00 am.
Madison County Covered Bridge Festival
October 10-11, 2026
The Madison County Covered Bridge Festival began in 1970 and now draws thousands to Winterset every second full weekend in October. The courthouse square features 150+ food and craft vendors, demonstrations, live music, kids’ activities, and more.
Want to visit the bridges? The Winterset Rotary Club offers guided bus tours throughout the weekend.
Be sure to stop at the Madison County Historical Complex for “History on the Hill,” with free admission, wagon rides, Civil War reenactments, and evening treats. Free shuttles run between the festival grounds and the historical complex.
Sunday also features a large car show near Winterset Elementary and the festival parade. Don’t miss Madison County’s signature annual event!
Winterset Festival of Lights
November 27, 2026
Join us in Winterset’s courthouse retail district for a holiday experience like none other!
5:00 pm – Live and lighted window displays start. Voting opens at the Chamber’s Welcome Center for your favorite window display. Food and beverages will be available on the west side of the courthouse lawn. Santa will be inside the courthouse for visits and your own photos.
Winter Solstice Market
December 11-12, 2026
Please join us for a two-day indoor holiday market featuring 40 curated arts, crafts, and food vendors in two locations around the Winterset Courthouse Square – the restored Winterset Livery building at 116 S. 1st Avenue, and the newly renovated Warehouse on 2nd (old Grip-Tite building) located at 213 N. 2nd Avenue.
Annual Meeting & Banquet
January, 2027 (Date TBA)
Join fellow Madison County Chamber of Commerce members as we celebrate the achievements of 2026 and look ahead to an exciting year in 2027!
The social hour starts at 5:00 pm, complete with games and prizes. Wine and beer will be available for purchase. Non-alcoholic beverages are included with your ticket. Dinner will be served buffet-style and is followed by our 2026 recap and awards ceremony.
Funds raised from the events hosted by the Chamber of Commerce, a nonprofit organization, directly support our annual operating budget, enabling us to continue serving and strengthening Madison County as a great place to live, work, and do business.