Friday, November 26, 2021
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, 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! The fun concludes with a showing of Elf at the Iowa Theater at 8:00 pm – free admission with a non-perishable food item.

Festival of Lights Parade Application

Saturday, November 27, 2021:
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!

Friday, December 10, 2021:
Lights! Christmas! Action

From 5:00 pm to 7:00 pm

Live window displays feature “Christmas around the World” all around the Winterset Courthouse Square. Enjoy live or lighted window displays and extended shopping hours!

Saturday, December 11, 2021:
Winter Solstice Market

From Noon to 6:00 pm

Shop for handcrafted gifts and enjoy holiday music, food and drink in this brand new indoor holiday market at the restored Winterset Livery!

Winter Solstice Market Application

January 21, 2022:
Madison County Chamber Banquet & Annual Meeting

Nominate a Business

May, 2022:
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 2022: Date TBA
Airing of the Quilts

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 – 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, 2022: 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, 2022:
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 at Earlham Freedom Fest.

July, 2022: Date TBA
9th 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, 2022: 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

July 20-24, 2022:
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, 2022: 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

October 8-9, 2022:
Madison County Covered Bridge Festival

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