This week in Madison County…
We need you!!
Many hands make light work, sign up to volunteer today!
Freshen up our Bridges
Madison County has once again received support through the Paint Iowa Beautiful grant program to help purchase paint to freshen up the iconic white exterior of our historic covered bridges!
Each year, it takes 2 crews of roughly 20 volunteers to get the job done and we need your help!
📅 Saturday, September 26
⏰ 8:00 AM–3:00 PM
📍 Madison County Covered Bridges
Grab your work clothes and join us for a day of giving back while helping preserve one of the things that makes Madison County so special. https://www.signupgenius.com/go/10C054FA9AF2FA5F5C16-65508828-paint
Covered Bridge Festival 2026
It takes a village to put on a festival of this size and we couldn’t do it without hundreds of volunteers like you!
Please click on the link below to sign up to help – even a couple of hours will go a long way to the success of the festival.
Sign up today! https://www.signupgenius.com/go/10C054FA9AF2FA5F5C16-64802542-2026#/
Tonight
Clash by Night
Thursday • September 24 • 7:00 pm
Throwback Thursday at The Iowa Theater
1/2 off popcorn on Throwback Thursday!
After being away for 10 years, Mae Doyle (Barbara Stanwyck) returns to her California hometown following an affair with a married politician, which came to an end when he died and his relatives sued for her inheritance. Mae begins dating Jerry (Paul Douglas), an amiable fisherman, while his bitter best friend, Earl (Robert Ryan), a cynic married to a burlesque dancer, finds himself attracted to her. Mae and Jerry marry, but soon she gets bored and starts an affair with just-divorced Earl. 1952, Rated PG, 1hr 45min
Walk Around the Square for Suicide Prevention Awareness
Thursday • September 24 • 12:00-12:30 pm
Winterset Town Square
Thank you to our sponsors!
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This Week!
Senior Speaker Series
Iowa Fraud Fighters: Outsmarting Today’s Scams
Friday • September 25 • 10:00 am
Bricker Price Block, Earlham
Movie at The Iowa Theater: Practical Magic 2
- Friday, September 25 – 7:00PM
- Saturday, September 26 – 7:00PM
- Sunday, September 27 – 2:00PM
Two witches must confront the dark curse that threatens to unravel their family once and for all.
2026 Rated PG-13, 2hr, 10min
This Weekend!
Madison County Farmers Market
Saturday • September 26 • 8:00 am-12:00 pm
Madison County Courthouse Lawn
Located in the heart of Winterset, Iowa, the Madison County Farmer’s Market is your go-to destination for fresh, locally grown produce, handmade goods, and a vibrant community experience. Every week, our market brings together farmers, artisans, and small businesses to offer high-quality products straight from the source.
Whether you’re shopping for seasonal fruits and vegetables, farm-fresh meats, baked treats, or handcrafted treasures, you’ll find something special at our market. Join us in celebrating the best of local agriculture, craftsmanship, and community spirit—we can’t wait to see you there!
Plant Share & Sale
Saturday • September 26 • 9:00 am-12:00 pm
Winterset Public Library
Racktoberfest: Food, Beer, Music & Games
Saturday • September 26
Big Rack Brew Haus
It’s almost here – Racktoberfest 2026!
This Saturday, we’re celebrating our 6th Annual Racktoberfest, our biggest event of the year! Join us on the 26th at 1 PM for:
- German Bier Games for adults – hammerschlagen, keg toss, & stein holding
- Kids games, including root beer stein holding & sack races
- Delicious food from White Smoke BBQ
- Lots of beer, fun, & prizes
- Live music by Black Dirt Ramblers starting at 6 PM
Then on Sunday, September 27, we’re proud to be part of the Madison County Fall Crawl from 11am – 5pm, with vendors right here on site. Big Rack will have Dog Town Gourmet Hotdogs, plus Big Rack beer on tap, of course!
Facebook Event Link: https://www.facebook.com/events/1554751909620101/
And don’t forget — Happy Hour Friday 4-6 PM to start the weekend off right!
Mark your calendars now, grab your friends, and come celebrate with us! go!!
It’s a GREAT day to be a Citizen—
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Bingo Bites & Autumn Delights
Saturday • September 26 • 2:00 pm
Homestead Assisted Living
334 N West View Drive, Osceola
Madison County Fall Crawl
Sunday • September 27 • 8:00 am-6:00 pm
Madison County, Iowa
The Madison County Fall Crawl is a small, local event near Winterset, IA that takes place on the last Sunday in September.
Take a drive with friends around Madison County to see 15 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 with live music, kid’s activities, 80+ vendors and food trucks. Earliest businesses opening at 9am. Varies by stop location.
Big Rack will be open 11am – 5pm and have Dog Town Gourmet Hotdogs, plus Big Rack beer on tap, of course!
Find more info here!
Evergreen & Lily: Fall Open House
Sunday • September 27 • 11:00 am-3:00 pm
Evergreen & Lily
Iowa: and the Broken Circle
Sunday • September 27 • 5:30 pm
at The Iowa Theater
Followed by a discussion with director Charlie Morris!
Iowa: and the Broken Circle is a documentary film made by Iowa City local, Charlie Morris, and a part of The Iowa Prairie Documentary Project. This movie explores the story of the land we call Iowa, tackling tough questions like why most of us don’t swim in the water any longer and why so many of us are getting cancer. It’s also a spotlight on the beauty of Iowa, land restoration, and how easily we could be doing the right thing. 2026, Rated NR, 1hr 30min
Thank you to our sponsors!
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Next Week
Sesame Street and the Great Elephant Adventure: Season Premiere Launch Party!
Saturday • October 2 • 2:00 pm
Winterset Public Library
Adaptive Theater Camp
Saturday • October 3 • 9:00 am-12:00 pm
The Winterset Stage
Hotter Than Hell Beef Stick Eating Competition
Saturday • October 3 • 4:00-6:00 pm
Wagner Locker
Nature Trivia
Saturday • October 3 • 5:30 pm
Madison County Conservation Center
Thank you to our sponsors!
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Coming Soon
2026 Covered Bridge Festival
Saturday • October 10 • 9:00 am-7:00 pm
Sunday • October 11 • 9:00 am-3:00 pm
Winterset Town Square
Please join us in Madison County, Iowa, for the 2026 Madison County Covered Bridge Festival! Saturday, October 10th, from 9:00 am to 7:00 pm, and Sunday, October 11th, from 9:00 am to 3:00 pm (parade starts at 3:00). Every second full weekend in October since 1970, the Winterset courthouse square fills with over 140 food, and arts and crafts vendors, continuous live music, children’s activities, and much more. Don’t miss Madison County’s signature annual event! $3.00 at the gate only! Children 11 & under are free.
WHS Alumni All Class Reunion
Saturday • October 10 • 5:00-8:30 pm
Jackson Building
WHS Alumni All Class Reunion
Saturday, October 10th from 5-8:30pm
Location: Jackson Building
All Alumni welcome
Madison County Genealogical Society: Full Text Search
Tuesday • October 6 • 6:00 pm
Winterset Public Library
LIVE WILD
From Herd to Harvest: What to Expect this Deer Season
Tuesday • October 6 • 6:00-7:00 pm
Madison County Conservation Center
Decades on the Orchard
Saturday • October 17 • 5:00-11:00 pm
Winterset Cidery
Get ready to rewind. For one day only, we’re taking over the orchard with nonstop music from the 60s through the 2000s. Winterset, lowa becomes the soundtrack of every era you love.
From classic rock to 90s alt to early-2000s emo anthems, each set is crafted to take you back!
Live on stage:
- Dirty Rotten Scoundrels
- Not Quite Brothers
- Emo Kids
Plus: - local vendors
- Food trucks serving up delicious eats
- Craft ciders, beer, and ice-cold beverages from lowa brewers Bring your crew, your blankets, and your love for every decade.
Spread out under the open sky, wander the orchard paths, or post up near the stage!
Unfiltered Events is creating a place to connect, celebrate, and feel rooted.
Tickets on sale now.
Haunted Harvest Festival
Saturday • October 24
Madison County Conservation Center
Trick or Treat Around the Square
Friday • October 30 • 3:30-5:00 pm
Winterset Town Square
🎃 Downtown Trick-or-Treating is Coming! 👻
In partnership with the City of Winterset, we’re excited to welcome families downtown for an afternoon of Halloween fun!
Friday, October 30th – 3:30–5:00 PM
Downtown Merchants: If you would like to participate, please plan to set up outside your front door to hand out treats during the event.
REMINDER: We will not be placing participation decals in business windows. Setting up outside will make it easy for families to see which businesses are participating as they make their way around downtown. If you are NOT located on the downtown square but would like to participate, reach out to the chamber and we will help find an available location for you.
We’re looking forward to a fun afternoon of costumes, treats, and community in Downtown Winterset!
Chamber Members: We would love to include your upcoming events in the weekly snapshot, Chamber Chat and The Citizen.
Chamber Chat is great for business-to-business communication, while The Citizen is the perfect way to reach the wider community!
To ensure you get included, please email your event information to communications@madisoncounty.com by the Friday before publication.
