All Events in Winterset

Discover the best things to do & events in Winterset. Explore concerts, meetups, open mics, art shows, music events and a lot more.

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Popular Events in Winterset

Sat, 08 Nov

Holiday Market on The Farm 2025

1578 North River Trail, Winterset, IA

4+ Interested
Sat, 25 Oct

Haunted Harvest Festival

Madison County Conservation Center
Fri, 10 Oct

LIVE MUSIC with Ryne Doughty @ THE SPEAKEASY

112 W Court Ave, Winterset, IA 50273-1545, United States
Fri, 17 Oct

PIEOWA Documentary - Iowa Theatre

Iowa Theatre
Fri, 10 Oct

Friday Night Magic!

104 N. 1st Avenue, Winterset, IA, United States, Iowa 50273
Sat, 18 Oct

Lean Into The Light: New Watercolors By Christine Hilbert

The Warehouse on 2nd

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Artists on tour near Winterset

Music events in Winterset

Sat, 25 Oct

Nashville Style Listening Event

2207 170th Drive, Winterset, IA, United States, Iowa 50273
Sat, 18 Oct

Live Music at Winterset Cidery

1638 Highway 169, Winterset, IA
Sat, 18 Oct

Willie Mac & The Lost Cousins / Music at the Winery

Covered Bridges Winery

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Festivals in Winterset

Sat, 11 Oct

Madison County Covered Bridge Festival

73 Jefferson Street, Winterset, IA, United States, Iowa 50273
Sun, 12 Oct

Covered Bridges Festival at Winterset Cidery

1638 Highway 169, Winterset, IA
Sat, 11 Oct

Winterset Rotary Covered Bridge Race 5K Walk/Run

Winterset City Park

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Meetups in Winterset

Sat, 08 Nov

Madison County's Most Wanted: Kick-off

2508 Pammel Park Trl, Winterset, IA 50273-8308, United States
Fri, 12 Dec

Winter Solstice Market

116 S 1st Ave, Winterset, IA 50273-1907, United States
Wed, 12 Nov

Cancer in Iowa: 99 Counties Project (Madison - Hybrid Event)

201 W Court Ave, Winterset, IA 50273-1604, United States

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Frequently Asked Questions

Which are the most trending events happening in Winterset today?

Here are the best events happening in Winterset today:

LIVE MUSIC with Ryne Doughty @ THE SPEAKEASY is happening on 10 Oct 2025 from 7:30 PM onwards at 112 W Court Ave, Winterset, IA 50273-1545, United States
Friday Night Magic! is happening on 10 Oct 2025 from 5:00 PM onwards at 104 N. 1st Avenue, Winterset, IA, United States, Iowa 50273
Friday Fun Nights is happening on 10 Oct 2025 from 5:00 PM onwards at 231 N 2nd Ave, Winterset, IA, United States, Iowa 50273

Which are the most trending events happening in Winterset this weekend?

Here are the best events happening in Winterset this weekend:

Outdoor Worship Service at Middle River Park is happening on Sun 12 Oct 2025 from 10:00 AM onwards at Middle River County Park, Winterset
Hunter Education Field Day Course is happening on Sat 11 Oct 2025 from 8:00 AM onwards at Madison County Sportsman Gun Club, Winterset
Madison County Covered Bridge Festival is happening on Sat 11 Oct 2025 from 9:00 AM onwards at 73 Jefferson Street, Winterset, IA, United States, Iowa 50273
Fall on the Flower Farm at PepperHarrow is happening on Sat 11 Oct 2025 from 9:00 AM onwards at 1809 S 4th Ave, Winterset, IA 50273-2908, United States
Live at Big Rack Brew Haus is happening on Sat 11 Oct 2025 from 6:00 PM onwards at 2475 Hiatt Apple Trl, Winterset, IA 50273-8113, United States
Covered Bridges Festival at Winterset Cidery is happening on Sun 12 Oct 2025 from 1:00 PM onwards at 1638 Highway 169, Winterset, IA