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.
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, 2023 (Date TBA):
Airing of the Quilts
Hosted by the Iowa Quilt Musuem, the Madison County Airing of the Quilts celebrates the history, tradition, and artistry of quilting in Iowa! Hundreds of quilts are displayed in dozens of historical and cultural landmarks across our picturesque county. This unique event is one that you don’t want to miss!
June, 2023 (Date TBA):
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 8, 2023 (Date TBA):
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.
July, 2023 (Date 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 Community Stage. Learn more on Facebook at St. Charles Old Settlers on Facebook and at scoldsettlers.org.
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 madisoncountyfair.net.
August, 2023 (Date TBA):
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 hinterlandiowa.com.
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, 2023: Dates TBA
Bells, Bows & Boutiques Tour
The Adel Partners, Madison County, and Indianola Chambers of Commerce have partnered up to create a self-guided holiday shopping and dining rural road trip through their communities, as well as the City of Earlham. Shoppers are encouraged to visit as many of these communities as they can for a shopping and dining experience like no other. Each town has a map highlighting their Chamber members’ retail, dining and beverage businesses, which visitors can pick up at select merchants in each community or access here. Over 55 shops, 24 restaurants, and 13 wineries/breweries/pubs are being featured throughout.
December, 2023: Date TBA
PJ Party with Santa (Winter Solstice Preview Night)
5:30 – 7:30 pm: Join us for a magical night at our 1st ever PJ Party with Santa! Kids will enjoy a meal (grilled cheese sandwich, chips & a beverage), a story time with Dio Ayala (Madison County Emergency Manager), a short musical program with Madison County Music Company, and a visit with Santa! Kids are encouraged to wear their PJs and bring their sleeping bag. Parents and grandparents can be the first to shop this special indoor holiday market while the kids are entertained!
December, 2023: Date TBA
Winter Solstice Market
Saturday: 10am – 4pm
Sunday: 12 – 4pm
Join us for a brand new event – 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!