May 7 - 4th Annual Winterset Wine Walk, 4-7 pm
Participating businesses around the town square each offer a sample of a different locally-made wine, as well as shopping specials, drawings for prizes, etc. Participants can purchase a commemorative wine glass at the Madison County Chamber of Commerce. Enjoy a car show sponsored by The Central Iowa Auto Club as well. One of our most popular events!

May 27-29 - John Wayne Birthday Celebration
Scheduled activities include a benefit dinner, live music, an auction of John Wayne collectibles and memorabilia, the dedication of the iconic jaunting sidecar from "The Quiet Man", an all-horse parade, a country barn dance, breakfast at the Winterset firehouse, and a 5K run/walk.

June 1-30 - All Iowa Shop Hop
Quilters rejoice in month-long store specials, activities and celebrations of all things quilting across the state. In Madison County, our very own Ben Franklin and Piece Works Quilt Shop will be participating.

June 10 - Ladies Night Out, 6-9 pm
Participating businesses around Winterset's town square put on a special night for our female residents and visitors. The first 200 ladies to pre-register for this event receive a swag bag when they arrive at the Madison County Chamber of Commerce and enjoy special shopping specials, pampering, wine tasting, food samples, girl time, and more, all around the square.

July 13-17 - Madison County Fair
Bring the whole family for events and activities like Impact Pro Wrestling, livestock and pet shows, evening grandstand events, an archery contest, stock rodeo, truck pull, carnival rides and games, food and much more.

August 5-6 - Hinterland Music Festival, St. Charles
Two days of music curated for all who love both music and the outdoors. The annual festival features a blend of music, camping, art, craft vendors, family engagement and more. Held at the Avenue of the Saints Amphitheater in St. Charles, Hinterland offers an unbelievable lineup featuring Willie Nelson, Ray Lamontagne, Cold War Kids, and many more!

The new Cobblestone Inn & Suites in Winterset offers visitors, including large groups, clean and comfortable accommodations just a few minutes from our historic town square. With 39 rooms, including 3 extended-stay suites, a hot breakfast bar, guest laundry, fitness facility, and dining specials and a full bar in their lounge, The Cobblestone is a great addition to Madison County and makes those overnight stays (and longer itineraries) a must!

In January, Winterset’s town square (consisting of 83 buildings) was officially designated an Historic District on the National Register of Historic Places. In the center of the square is the impressive Madison County Courthouse, rebuilt in 1876 of native limestone, also on the National Register of Historic Places. The interior woodwork and twin staircases are made from locally milled oak and walnut. Writings and drawings from incarcerated persons from the early 1900s can still be seen on the third floor courthouse wall. We are all proud of the efforts of a great team of local researchers who made this incredible achievement possible!