Winterset Events in October

Events in October in Winterset

With a bunch of festivals in October 2025 in Winterset queued up, there is a lot to catch on! From being a spectator at all the cool festivals to attending some interesting events in October in Winterset there is all the fun awaiting you this month. Take a tour to this interesting guide or list of things to do in Winterset in October 2025 and make the most of your holidays and weekends!

Trending events in october in Winterset

Tue, 07 Oct

•

1638 Highway 169, Winterset, IA

Ladies Night at Winterset Cidery
Sat, 04 Oct

•

1026 N 8th Ave, Winterset, IA, United States, Iowa 50273

Ladies Bunco Night
Sat, 04 Oct

•

1578 North River Trail, Winterset, IA

Pumpkin Palooza
Sat, 25 Oct

•

2207 170th Drive, Winterset, IA, United States, Iowa 50273

Nashville Style Listening Event
Sat, 04 Oct

•

1638 Highway 169, Winterset, IA

Live Music at Winterset Cidery

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Most popular events in october in Winterset

Sat, 18 Oct

•

Covered Bridges Winery

Willie Mac & The Lost Cousins / Music at the Winery
Sat, 18 Oct

•

The Warehouse on 2nd

Lean Into The Light: New Watercolors By Christine Hilbert
Sat, 11 Oct

•

1638 Highway 169, Winterset, IA

Covered Bridges Festival at Winterset Cidery
Sat, 11 Oct

•

Madison County Sportsman Gun Club

Hunter Education Field Day Course
Thu, 09 Oct

•

111 s 1st Ave, Winterset, IA

Bi-Weekly Trivia @ The Honey Lounge

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Upcoming events in october in Winterset

Sat, 18 Oct

•

Covered Bridges Winery

Willie Mac & The Lost Cousins / Music at the Winery
Sat, 18 Oct

•

The Warehouse on 2nd

Lean Into The Light: New Watercolors By Christine Hilbert
Sat, 11 Oct

•

1638 Highway 169, Winterset, IA

Covered Bridges Festival at Winterset Cidery
Sat, 11 Oct

•

Madison County Sportsman Gun Club

Hunter Education Field Day Course
Thu, 09 Oct

•

111 s 1st Ave, Winterset, IA

Bi-Weekly Trivia @ The Honey Lounge
Sun, 05 Oct

•

Winterset Cidery

Cake Decorating Class: 101 (at Winterset Cidery)
Sat, 11 Oct

•

73 Jefferson Street, Winterset, IA, United States, Iowa 50273

Madison County Covered Bridge Festival

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Events in October from nearby cities

Trending tags in Winterset

ladies-night baking cupcakes barbeque running

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Entertainment

Live Music

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Upcoming Events in October in Winterset

Date	Event	Venue
09 Oct 2025	Bi-Weekly Trivia The Honey Lounge	111 s 1st Ave, Winterset, IA
12 Oct 2025	Outdoor Worship Service at Middle River Park	Middle River County Park, Winterset
01 Oct 2025	15th Annual Healthiest State Walk	Madison County Courthouse, Winterset

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