Saturday, September 12, 2020:
Winterset Wine Walk

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.

A few changes are in place for 2020:

  • 50 tickets for each half hour of the event will be available in order to spread out attendance.
  • Per public health recommendations, individual food samples with the wine pairings will not be offered. Food will be available for sale by the 2020 Class of the Madison County Leadership Institute.
  • Please observe social distancing guidelines and wear face coverings where possible.

Canceled for 2020:
Madison County Covered Bridge Festival

We look forward to seeing you again in 2021!

January, 2021 (date TBA):
Annual Meeting & Awards Night Banquet

Join the Chamber membership at the 2021 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, 2021 (date TBA):
Winterset Chocolate Walk

10:00 am to 4:00 pm

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!

Memorial Day Weekend, 2021:
John Wayne Birthday Celebration

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 movie screenings at the historic Iowa Theater, an all-horse parade, a benefit dinner and auction and, as always, special guest stars. For further information, visit the John Wayne Birthplace & Museum Website or call toll free 877-462-1044.

Father’s Day Weekend, 2021:
The Great Madison County Scavenger Hunt

Do you crave some fun in these times of social distancing? Are you looking for something different to do with Dad on Father’s Day weekend?  Do you just need to get out of the house and enjoy our beautiful community?  We’ve got the answer! Join us for The Great Madison County Scavenger Hunt to search, scavenge, and socially distance from your car! 

June, 2021:
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, 2021:
Freedom Fest, Earlham
Sesquicentennial (150th Anniversary!)

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 21-25, 2021:
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.

July, 2021:
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.

August 6-8, 2021:
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.