May 11, 2024
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 24 & 25, 2024
John Wayne Birthday Celebration

The 2024 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!

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 5-8, 2024
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 15, 2024
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, 2024
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 12, 2024
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, 2024 (Dates TBA)
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 17-21, 2024
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 2-4, 2024
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

September 22, 2024
Paint Madison County, A Plein Air Festival

Join the Madison County Chamber of Commerce as it hosts its first annual Paint Madison County, A Plein Air Festival. The public will visit 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 an evening reception.

Artists will create in the open air 9am-1pm and a reception will follow 4-7pm, hosted at Covered Bridges Winery. Attendees will have the opportunity to purchase participating artists’ work.

Paint Madison County Application

September 29, 2024
Madison County Fall Crawl

Take a drive with friends around Madison County to see small local businesses in their rural setting. There are a few stops along the crawl that have normal business hours where you can grab a glass of coffee, wine, cider, beer, or a bite to eat. The fall crawl is a free event for the entire family, with lots of fun things to do and over 60 vendors. Earliest businesses open at 9 am. 

Suggested starting point: Pammel Park Coffee Company for a cup of freshly roasted coffee.

As a general rule of thumb: Businesses within Winterset and to the South and West, open at 9 am. Businesses to the East and North of Winterset are open at 10/11+ am.

Business names, pictures, social media links, clickable google map addresses, hours, & vendors by location are all listed on the website.

Learn More

October 12-13, 2024:
Madison County Covered Bridge Festival

Two full days of arts & crafts, food, demonstrations, covered bridges, and special events. Don’t miss Madison County’s signature annual event!

Friday, November 29, 2024
Winterset Festival of Lights

Join us in Winterset’s courthouse retail district for a holiday experience like none other! At 5:00 pm, the whole family will enjoy food, live and lighted window displays, free horse-drawn carriage rides, extended shopping hours, roaming carolers, and interactions with Santa, all around the Madison County courthouse. A lighted parade gets underway at 7:15 pm. 

Saturday, November 30, 2024:
Small Business Saturday

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

December 6 & 7, 2024
4th 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, 2025: 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!