May 13, 2023
Winterset Wine Walk

A great outing enjoy with Mom on Mother’s Day weekend! Join the Madison County Chamber of Commerce, downtown Winterset merchants, and area wineries for shopping, wine sampling, music, and more. Must be 21 years of age or older to participate; wristbands will be required.


May 26 & 27, 2023
John Wayne Birthday Celebration

The 2023 John Wayne Birthday Celebration will be bigger and better than ever. Stay tuned to the museum’s Facebook page and website for further announcements. You’ll want to be there!

May 31 – June 3, 2023
Iowa Quilt Festival

The Iowa Quilt Festival, formerly known as the Airing of the Quilts, celebrates the history, tradition, and artistry of quilting in Iowa!
Learn More & Purchase Tickets

June – August (no July 4):
Levitt Amp Music Series

In Earlham City Park, every Sunday from 6-9pm. Find more details about the weekly musical guests, food and entertainment here: Levitt AMP Earlham Music Series

June 17, 2023:
Macksburg National Skillet Throw

Featuring a parade, pedal tractor pull, RC car demonstration, food and craft vendors, and of course, a skillet throw. See Macksburg National Skillet Throw for more information.

July 4, 2023
Earlham Freedom Fest

Celebrate Independence Day in Earlham! Take part in a street dance, a parade, a pancake breakfast, tons of contests (including watermelon-eating and bubble gum blowing), and fireworks, to name just a few. Find more information on Facebook @EarlhamFreedomFestival.

July 7, 2023
Annual Chamber of Commerce Golf Outing

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 at 8:00 am, shotgun start at 9:00 am. Presented by Fareway Grocery Store and Union State Bank.

Download Registration Form

July 8, 2023
Paint Madison County, A Plein Air Festival

The public will visit up to 20 curated artists as they artistically capture the gems of Madison County. Activities and locations will include local vendors/businesses, an opportunity for children to partake, and the evening will end with a cocktail reception with a private viewing of the artists’ creations.

Download Registration Form

July 14-15, 2023
Old Settlers Days, Saint 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 Community Stage. Learn more on Facebook at St. Charles Old Settlers on Facebook and at

July 19-23, 2023
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! View the full schedule and details as they develop at

August 4-6, 2023
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 a the Avenue of the Saints Amphitheater in St. Charles. View the full lineup and details as they develop at

October 14-15, 2023:
Madison County Covered Bridge Festival

Two full days of arts & crafts, food, demonstrations, covered bridges, and special events to celebrate being reunited!

Friday, November 24, 2023
Festival of Lights

Join us in Winterset’s courthouse district for a holiday experience like none other! At 5:00 pm, the whole family will enjoy food, live entertainment, live and lighted window displays, free horse-drawn carriage rides, and photos with Santa, all around the Madison County courthouse. A lighted parade featuring holiday movies gets underway at 7:15 pm, ending with an appearance by Santa who will light up the courthouse square!

Saturday, November 25, 2023:
Small Business Saturday

Shop small, local businesses and enjoy special holiday festivities throughout the day.

7-11 am – Start with a pancake breakfast at the American Legion Hall hosted by the local Kiwanis. $6 per person.

10 am to 2 pm – Enjoy a free horse-drawn carriage ride around the courthouse square while shopping in Winterset’s award-winning retail district!

December 8 & 9, 2023
3rd Annual Winter Solstice Market

Friday, December 8: 6:00 to 9:00 pm
Saturday, December 9: 10:00 am to 4:00 pm

Join us for a two-day indoor shopping experience featuring 26 curated arts, crafts and food vendors in the newly restored Winterset Livery building on the Winterset Courthouse Square, 116 S. 1st Ave. Savor the sights, sounds and scents of the holiday season while shopping for handcrafted items for everyone on your list.

January, 2024: Date TBA
Madison County Chamber Banquet & Annual Meeting

Join the Madison County Chamber of Commerce membership as we celebrate the achievements of 2023 and look ahead to an exciting year in 2024!