Events in January in Winterset

• Sat, 28 Feb, 2026 - 05:30 PM

  Madison County Fair Capital Campaign Kickoff Dinner

  Jackson Building, Madison County Fairgrounds, 1146 W Summit Street, Winterset, IA 50273

  75+ Interested
• Sat, 07 Mar, 2026 - 10:00 AM

  Madison County's Most Wanted

  2508 Pammel Park Trl, Winterset, IA 50273-8308, United States
• Sat, 07 Mar, 2026 - 01:00 PM

  Make Chunky Knit Blankets at Covered Bridges Winery in Winterset!

  Covered Bridges Winery

  41+ Interested
• Sun, 22 Feb, 2026 - 11:00 AM

  Taco Bar Fundraiser for Madison County 4-H & FFA Youth

  Madison County Fair, Iowa

  27+ Interested
• Sun, 29 Mar, 2026 - 02:00 PM

  Aaron Simmons / Sunday Wine Down

  2207 170th Drive, Winterset, IA, United States, Iowa 50273
• Sat, 14 Mar, 2026 - 08:00 AM

  March 14th Farmers Market

  The Warehouse on 2nd

  742+ Interested
• Sat, 28 Mar, 2026 - 05:00 PM

  Big Rack Brew Haus (Jesse's Double Nickel Hoedown)

  Big Rack Brew Haus

  59+ Interested
• Sat, 17 Oct, 2026 - 05:00 PM

  Decades on the Orchard

  Winterset Cidery

  186+ Interested
• Fri, 06 Mar, 2026 - 05:30 PM

  Madison County Covered Bridge Chapter's 2026 Annual Banquet and Auction

  1146 W Summit St, Winterset, IA 50273-2276, United States

  118+ Interested
• Fri, 06 Mar, 2026 - 06:00 PM

  Princess Tea Party

  2611 Highway 169, Winterset, IA, United States, Iowa 50273

  32+ Interested
• Sun, 01 Mar, 2026 - 05:30 PM

  Wine Dinner- Basque Inspired

  1511 N. John Wayne Dr., Winterset, IA

  10+ Interested
• Sat, 28 Feb, 2026 - 10:00 AM

  Stuart Little, a production of the Pat Nelson Children's Theater

  121 John Wayne Drive, Winterset, IA, United States, Iowa 50273

  8+ Interested
• Sat, 28 Mar, 2026 - 06:30 PM

  Looking4Luke/ Music at the Winery

  Covered Bridges Winery

  42+ Interested
• Sat, 09 May, 2026 - 05:30 PM

  A Picnic in the Forest

  Iris Aisle

  USD 150
• Sun, 22 Feb, 2026 - 02:00 PM

  Danny Grause / Music at the Winery

  Covered Bridges Winery

  21+ Interested