Special Events

Shop Madison County this holiday season for a hometown shopping experience like no other! In Winterset, enjoy a pancake breakfast, strolling carolers, horse-drawn carriage rides, and take part in a community warm boot and mitten drive. Visit the “Made With Love” Pop-Up Shop, the Teddy Bear Workshop, and take in a holiday movie!

For more information, click View More!

Show your love for Madison County’s small businesses, and #ShopSmall this holiday season!

Kick off the holiday season in Madison County!
Highlights include live music, hot food and drinks, a lighted Christmas parade, strolling carolers, movies at The Iowa Theater, and a visit by Santa Claus!
5:00-8:00 pm; Courthouse Square in Winterset

From 5:00 to 7:00 pm, participating stores around Winterset’s courthouse square will have live and in-motion holiday window displays, plus extended hours for your holiday shopping needs. Shopping in pajamas is encouraged!

From 10:00 am to 12:00 pm, come out to the Madison County Historical Complex for some fun with Santa Clause, photos, and cookie decorating. Complementary photos taken with Santa.

From 1 – 5 pm. Visit eight churches in Earlham and Winterset decked out for the holidays and full of Christmas spirit! Participating churches include First Presbyterian, St. Paul Lutheran, Faith Lutheran (at the Zion Church at the Madison County Historical Complex), First Christian and Oak Grove Church in Winterset, as well as Early Chapel Christian, Penn Center Methodist and First Presbyterian in Earlham. Tickets, information and hospitality will be available at the Madison County Chamber of Commerce Welcome Center in Winterset and the Bricker-Price Block in Earlham. Tickets are $13 in advance and $15 day-of, and proceeds benefit all participating churches. Each church will offer something special – from refreshments to live music to handmade items for sale. Bricker-Price Block will also be holding a craft/vendor fair upstairs from 9am - 5pm that day (no ticket necessary).

Join the Chamber membership at the 2019 Annual Meeting & Awards Night Banquet at the Jackson Building on the Madison County Fairgrounds. Highlights include a fun, relaxing social hour, scrumptious meal, plus awards and honors for deserving businesses and organizations in our community.

Participating businesses around Winterset’s courthouse square offer chocolate samples, shopping specials and more in celebration of Valentine’s Day. No registration required, just enjoy!

One of our most popular events! Sample locally-made wine and enjoy shopping specials, prizes and more at participating businesses around Winterset’s town square. Participants may purchase a commemorative wine glass at the Chamber of Commerce. Click "View More" to purchase tickets.

The John Wayne Birthplace & Museum has announced that legendary western performer Red Steagall will headline this year's John Wayne Birthday Celebration May 25 & 26! The weekend kicks off with a screening of "Red River"(1948) on May 25 at Winterset's historic Iowa Theater. Returning Celebration favorites on Saturday, May 26, will be Breakfast at the Firehouse and the Birthday Celebration's 5K Run/Walk, followed by an all-horse parade through picturesque Winterset. Wrapping up the celebration will be a Benefit Dinner featuring a musical performance by Red Steagall and an auction of John Wayne collectibles and memorabilia. For further information and reservations, click the View More link below or call 515-462-1044.

The Madison County Chamber of Commerce is proud to present the first Women's Weekend in Winterset - a special weekend of classes, workshops, demos, entertainment, pampering, dining, shopping and more! Click here to download a printable schedule, or click the "View More" button to see the full lineup of events and online registration.

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events are free to attend. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars!

Featuring a parade, pedal tractor pull, RC car demo, food and craft vendors, and of course, a skillet throw. Click to see the full lineup as it develops.

Celebrate Independence Day in Earlham! Take part in a street dance, a parade, a pancake breakfast, tons of contest (including watermelon-eating and bubble gum blowing!), and fireworks, to name just a few. More details coming soon.

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events are free to attend. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars!

The Old Settlers event celebrates family fun and community involvement. St. Charles, Iowa is proud of its heritage and traditions. Many Old Settlers worked hard to build this little community! Lots of family entertainment all weekend long, from Cow Pie Bingo to entertainment on the new Community Stage.

Bring the whole family for events and activities, livestock and pet shows, grandstand events, contests, carnival rides and games, food and much more!

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events are free to attend. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars!

Two days of music curated for all who love both music and the great outdoors. This annual festival features a blend of live music, camping, art, craft and food vendors, family activities and more. Held at the Avenue of the Saints Amphitheater in St. Charles.

We invite you to visit the 2019 Madison County Covered Bridge Festival on October 12th & 13th to experience the world famous covered bridges, crafts and old-time demonstrations, annual quilt and car shows, cowboys from the wild west, continuous entertainment, family fun — and the many people and places that make it a very special place to visit and a beautiful place to call “home.”