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Best events in
Winterset

Life in Winterset often revolves around its historic town square, where community events and things to do in Winterset, IA are a regular occurrence. The town celebrates its agricultural roots and famous covered bridges with a calendar full of annual festivals and local markets. Evenings can be spent enjoying live music at a local cidery or catching a film at the restored Iowa Theater.

For a classic small-town evening, catch a film or live performance at the historic Iowa Theater, a centerpiece of the courthouse square.
The area's agritourism scene offers relaxing afternoons with live music at venues like Winterset Cidery or Covered Bridges Winery.
The Winterset Stage presents a variety of productions, from musicals to concerts, providing live theater experiences for all ages.

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Pork + Pinot presented by The Iowa Pork Producers primary image

Pork + Pinot presented by The Iowa Pork Producers

Fri, Oct 16 • 5:00 PM

Middlebrook Farm

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Pilates at Magnolia Farms

Sun, Oct 18 • 1:00 PM

Magnolia Farms

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Pumpkins & Petals primary image

Pumpkins & Petals

Sat, Oct 24 • 5:30 PM

Eden Coffee

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Second Annual Truman Tough Basketball Clinic

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Prairieview School

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2026 November/December dsm magazine Unveiling

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Iowa Weight Loss Specialists - Iowa Specialty Hospitals and Clinics - Des Moines

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FREAKOUT 2026 ft. Medicine Place | Halloween Rave | Des Moines Area, 18+ primary image

FREAKOUT 2026 ft. Medicine Place | Halloween Rave | Des Moines Area, 18+

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Avenue of the Saints Amphitheater and Event Center

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11/17 - Clive, IA - Friendsgiving in Wine Country primary image

11/17 - Clive, IA - Friendsgiving in Wine Country

Tue, Nov 17 • 7:00 PM

Cooper’s Hawk Winery & Restaurant

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Back to the Classics: Rum, Rhum and Ron! primary image

Back to the Classics: Rum, Rhum and Ron!

Wed, Nov 18 • 7:00 PM

BeerStyles Taproom & Gastropub

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Pork + Pinot presented by The Iowa Pork Producers primary image

Pork + Pinot presented by The Iowa Pork Producers

Fri, Oct 16 • 5:00 PM

Middlebrook Farm

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Pilates at Magnolia Farms

Sun, Oct 18 • 1:00 PM

Magnolia Farms

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Pumpkins & Petals primary image

Pumpkins & Petals

Sat, Oct 24 • 5:30 PM

Eden Coffee

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Second Annual Truman Tough Basketball Clinic primary image

Second Annual Truman Tough Basketball Clinic

Sun, Oct 25 • 12:30 PM

Prairieview School

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2026 November/December dsm magazine Unveiling primary image

2026 November/December dsm magazine Unveiling

Tue, Oct 27 • 5:00 PM

Iowa Weight Loss Specialists - Iowa Specialty Hospitals and Clinics - Des Moines

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FREAKOUT 2026 ft. Medicine Place | Halloween Rave | Des Moines Area, 18+ primary image

FREAKOUT 2026 ft. Medicine Place | Halloween Rave | Des Moines Area, 18+

Sat, Oct 31 • 8:00 PM

Avenue of the Saints Amphitheater and Event Center

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11/17 - Clive, IA - Friendsgiving in Wine Country primary image

11/17 - Clive, IA - Friendsgiving in Wine Country

Tue, Nov 17 • 7:00 PM

Cooper’s Hawk Winery & Restaurant

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Back to the Classics: Rum, Rhum and Ron! primary image

Back to the Classics: Rum, Rhum and Ron!

Wed, Nov 18 • 7:00 PM

BeerStyles Taproom & Gastropub

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett primary image

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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HBR Book Webinar: Resilient Optimism primary image

HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD primary image

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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Biodiversity Law and Governance Day 2026 primary image

Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett primary image

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Witch hunts and real lives primary image

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026 primary image

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Maxwell

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Altoona

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Bondurant

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Polk City

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Des Moines

26 miles away

West Des Moines

21 miles away

Ankeny

33 miles away

Windsor Heights

24 miles away

Urbandale

24 miles away

Clive

22 miles away

Waukee

20 miles away

Johnston

28 miles away

Ames

50 miles away

Cumming

16 miles away

Greenfield

23 miles away

Perry

35 miles away

Norwalk

21 miles away

Adel

19 miles away

Redfield

20 miles away

Indianola

24 miles away

Grimes

26 miles away

Maxwell

49 miles away

Altoona

35 miles away

Bondurant

38 miles away

Polk City

34 miles away

Points of Interest near Winterset

Cutler Donahoe Covered Bridge

Covered Bridges Scenic Byway

Frequently asked questions about Winterset

Where can I find live music events in Winterset?

Winterset Cidery is a popular spot for live music in a rustic setting. They host performers for recurring afternoon events, and other local venues like Covered Bridges Winery and Big Rack Brew Haus also feature live acts throughout the year.

What are some family-friendly things to do in Winterset?

The Winterset Stage often has productions suitable for all ages, including children's theater. Additionally, the annual Winterset Festival of Lights and the seasonal Madison County Farmers Market on the courthouse lawn are great family-oriented events.

Are there any major annual festivals in Winterset?

The Madison County Covered Bridge Festival is the area's signature annual event each October. The festival fills the historic square with craft vendors, food, and live entertainment, celebrating the region's famous bridges and local culture.

What's the nightlife like around the historic courthouse square?

Nightlife in Winterset is centered on relaxed social gatherings. The Drift taproom offers Iowa craft beers and cocktails, while the Iowa Theater shows films and hosts performances. Local breweries and wineries often have evening hours for music.

How can I experience the local arts and crafts scene?

The Winter Solstice Market is a great event to find curated arts and crafts. Held in early December, this indoor market brings together many local and regional artisans. The Madison County Farmers Market also features handmade goods.

Which local venues host food and drink events?

Local producers are highlighted at the seasonal Madison County Farmers Market on the courthouse lawn. For craft beverages, places like The Drift, Big Rack Brew Haus, and Winterset Cidery host tastings and music events that create a social atmosphere.

What are some date night ideas in Winterset?

A movie at the historic Iowa Theater followed by drinks at The Drift on the square is a classic date night. For something more relaxed, an afternoon of live music and cider tasting at Winterset Cidery offers a memorable experience.

Is there a place to find unique markets or shopping events?

Winterset Livery, a restored historic building, hosts various market events throughout the year. For holiday shopping, the two-day Winter Solstice Market gathers numerous vendors, and the annual Covered Bridge Festival features a large craft fair.