January 30, 2020: Annual Meeting
& Awards Night Banquet
Join the Chamber membership at the 2020 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. If you'd like to nominate an individual or business for an award, use this link.
February 8, 2020: Winterset Chocolate Walk
10am to 4pm
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!
Saturday, May 9, 2020: Winterset Wine Walk
4pm to 7pm
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.
Memorial Day weekend, 2020: John Wayne Birthday Celebration
Over the weekend of May 22 & 23, in the Madison County community where John Wayne was born (May 26, 1907) legions of enthusiasts will arrive to celebrate Wayne's birthday and to enjoy multiple screenings of "Big Jake" at the historic Iowa Theater, an all-horse parade, a benefit dinner & auction and, as always, special guest stars. Confirmed are actor Christopher Mitchum and musical headliner Mary Stuart.
For further information visit: www.johnwaynebirthplace.museum or call toll-free 877-462-1044.
June, 2020 ( date TBA): Macksburg National Skillet Throw
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.
June, 2020 (date TBA): Women's Weekend in Winterset
The Madison County Chamber of Commerce is proud to present the second annual Women's Weekend in Winterset - a special weekend of classes, workshops, demos, entertainment, pampering, dining, shopping and more.
July 4, 2020: Freedom Fest, Earlham
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.
July, 2020 (dates TBA): Old Settlers Days, St. Charles
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.
July 15-19, 2020: Madison County Fair
Bring the whole family for events and activities, livestock and pet shows, grandstand events, contests, carnival rides and games, food and much more!
July 31-August 2, 2020: Hinterland Music Festival
Three 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.
September, 2020 (date TBA): Winterset Ladies Night Out
Just for the ladies -- the merchants and businesses around the courthouse square team up to bring you a special night of shopping, pampering, photos, sales, sampling and more! 6pm to 9pm.
October 10 & 11, 2020: Madison County Covered Bridge Festival
We invite you to visit the 2020 Madison County Covered Bridge Festival on October 10th and 11th 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.”
Friday, November 27, 2020: Festival of Lights
Kick off the holiday season with a visit from Santa Claus, lighted Christmas parade, live music, and more! Highlights include:
Live Music - Enjoy entertainment from local musicians to get you in the holiday spirit! Music stage is on the west side of the courthouse steps.
Santa Claus - Everyone's favorite jolly ol' elf will be in the courthouse to hear what's on your child's wish list, and pose for photos!
Hot Food & Drinks - Warm up with cocoa, cider, soup, and more as you anticipate the start of the parade and Santa's official arrival!
Holiday Shopping with Local Businesses - Venture into the warm, cozy stores on the square to find unique gifts for everyone on your shopping list!
Lighted Parade - Enjoy festively-decorated floats traveling around all sides of the square!
"Elf" at the Iowa Theater following the lighted parade. FREE admission with the donation of a non-perishable food item for local food pantry.
Warm burn barrels & holiday cheer!
Parade Theme: "Joy to the World"
November 28, 2020: Small Business Saturday
9:00 am - 5:00 pm
Shop Madison County this holiday season for a hometown shopping experience like none other! In Winterset, start your day with a pancake breakfast, visit reindeer on the Hill at the Madison County Historical Complex, and enjoy horse-drawn carriage rides. Visit the “Made With Love” Pop-Up Shop, bring home crafts from the Holiday Make-and-Take at the Winterset Public Library, and shop for everyone on your list in our cozy, unique shops and boutiques. Take in a holiday movie and view a special display of nativity sets to finish your day!
For more information, click View More! Show your love for Madison County’s small businesses, and #ShopSmall this holiday season!
December, 2020 (date TBA): "Lights, Christmas, Action" Downtown Winterset
From 5:00 to 7:00 pm, The Winterset Merchants Group invites you to enjoy "Lights...Christmas...Action!" on Thursday, December 12! Participating merchants will feature live or in-motion holiday displays in their store windows. Take this special opportunity to enjoy holiday shopping as merchants extend shopping hours, offer holiday treats and deals, and enjoy the creativity and cleverness of our local retailers! The overall theme for the displays is "Joy to the World". Vote for your favorite displays in the areas of 1) Best Use of Theme, 2) Best Use of Merchandise, 3) Best Use of Space, and 4) Best Use of Lights.