All Upcoming events

• Fri, 28 Nov, 2025 - 05:00 PM

  2025 Winterset Festival of Lights

  63 Jefferson street, Winterset IA 50273
• Fri, 12 Dec, 2025 - 06:00 PM

  Winter Solstice Market

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

  727+ Interested
• Fri, 14 Nov, 2025 - 05:00 PM

  Annual Client and Friends Party

  Lakeview Country Club - LVCC

  70+ Interested
• Sat, 22 Nov, 2025 - 01:00 PM

  Bottle Extravaganza at Winterset Cidery

  1638 Highway 169, Winterset, IA

  96+ Interested
• Sat, 15 Nov, 2025 - 02:00 PM

  Door Hanger Craft Class

  2207 170th Trl, Winterset, IA 50273-8200, United States

  18+ Interested
• Sat, 29 Nov, 2025 - 07:00 PM

  21+ Jingle Jammie Jam

  111 s 1st Ave, Winterset, IA

  174+ Interested
• Sat, 06 Dec, 2025 - 10:00 AM

  Ladies Brunch & Bubbles at Winterset Cidery

  1638 Highway 169, Winterset, IA

  118+ Interested
• Sun, 07 Dec, 2025 - 12:00 PM

  Santa & Mrs Claus at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Fri, 28 Nov, 2025 - 11:00 AM

  Black Friday - Cidery Style

  1638 Highway 169, Winterset, IA

  67+ Interested
• Wed, 26 Nov, 2025 - 05:00 PM

  Thanksgiving Eve Date Night at Winterset Cidery

  1638 Highway 169, Winterset, IA

  100+ Interested
• Sat, 15 Nov, 2025 - 09:00 AM

  PepperHarrow Holiday Farm Shop

  1809 S 4th Ave, Winterset, IA 50273-2908, United States

  174+ Interested
• Wed, 12 Nov, 2025 - 05:30 PM

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

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

  5+ Interested
• Sat, 22 Nov, 2025 - 08:30 AM

  Winterset Holiday Hop

  Winterset, Iowa
• Sat, 06 Dec, 2025 - 09:00 AM

  Visit Santa at F&M!

  101 West Jefferson St, Winterset, IA, United States, Iowa 50273
• Tue, 11 Nov, 2025 - 05:00 PM

  BINGO!

  Jackson Building, Madison County Fairgrounds, 1146 W Summit St., Winterset, IA
• Sat, 06 Dec, 2025 - 06:00 PM

  MC Line @ The Honey Lounge

  Haynes Homestead and The Honey Lounge

  31+ Interested
• Thu, 20 Nov, 2025 - 07:00 PM

  A Gift for Rebecca

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

  29+ Interested
• Sat, 13 Dec, 2025 - 10:00 AM

  Madison County's Most Wanted: Encounters with the Most Wanted

  Winterset Public Library

  15+ Interested
• Sat, 20 Dec, 2025 - 08:00 AM

  Inclusive Holiday Photo Event

  Winterset Public Library

  25+ Interested
• 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
• Tue, 18 Nov, 2025 - 06:30 PM

  Sourdough Starter Class

  111 s 1st Ave, Winterset, IA, United States, Iowa 50273

  22+ Interested
• Mon, 08 Dec, 2025 - 05:30 PM

  Cocoa & Photos With Santa

  122 S John Wayne Dr, Winterset, IA, United States, Iowa 50273

  171+ Interested
• Tue, 11 Nov, 2025 - 06:30 PM

  Holiday Paint & Pints at Winterset Cidery!

  Winterset Cidery

  74+ Interested
• Sat, 29 Nov, 2025 - 09:00 AM

  Sensory Play & Social Hour

  Winterset Public Library

  6+ Interested
• Fri, 12 Dec, 2025 - 10:00 AM

  Winterset Christmas Open House

  101 West Jefferson St, Winterset, IA, United States, Iowa 50273

  9+ Interested
• Sun, 07 Dec, 2025 - 02:00 PM

  🎄 Christmas Door Swag Workshop 🎄

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

  13+ Interested
• Sat, 22 Nov, 2025 - 08:30 AM

  Annual Holiday Hop at Saint Joseph Church

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

  19+ Interested
• Sun, 16 Nov, 2025 - 02:00 PM

  Covered Bridges Winery

  Covered Bridges Winery

  76+ Interested
• Sat, 06 Dec, 2025 - 12:00 PM

  Mead and Merriment: A Crafting Wonderlan

  Haynes Homestead and The Honey Lounge

  10+ Interested
• Fri, 12 Dec, 2025 - 09:00 AM

  Esther Unearthed at Winterset's Winter Solstice

  116 S 1st Ave, Winterset, Iowa

  9+ Interested