All Upcoming events

• Sat, 08 Nov

  Holiday Market on The Farm 2025

  1578 North River Trail, Winterset, IA
• 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, 25 Oct

  Nashville Style Listening Event

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

  Lean Into The Light: New Watercolors By Christine Hilbert

  The Warehouse on 2nd
• Sun, 12 Oct

  Outdoor Worship Service at Middle River Park

  Middle River County Park
• Sat, 11 Oct

  Hunter Education Field Day Course

  Madison County Sportsman Gun Club
• Sat, 11 Oct

  Madison County Covered Bridge Festival

  73 Jefferson Street, Winterset, IA, United States, Iowa 50273
• Sat, 08 Nov

  Madison County's Most Wanted: Kick-off

  2508 Pammel Park Trl, Winterset, IA 50273-8308, United States
• Sat, 18 Oct

  Willie Mac & The Lost Cousins / Music at the Winery

  Covered Bridges Winery
• Sat, 11 Oct

  Fall on the Flower Farm at PepperHarrow

  1809 S 4th Ave, Winterset, IA 50273-2908, United States
• Sat, 29 Nov

  21+ Jingle Jammie Jam

  111 s 1st Ave, Winterset, IA
• Sat, 25 Oct

  GATSBY/ROARING 20'S NIGHT

  112 W Court Ave, Winterset, IA 50273-1545, United States
• Sat, 25 Oct

  Seasonal Cider Release at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Sat, 11 Oct

  Live at Big Rack Brew Haus

  2475 Hiatt Apple Trl, Winterset, IA 50273-8113, United States
• Tue, 21 Oct

  Field to Fork at Winterset Cidery

  Winterset Cidery
• Fri, 10 Oct

  Friday Fun Nights

  231 N 2nd Ave, Winterset, IA, United States, Iowa 50273
• Sat, 18 Oct

  Live Music at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Thu, 23 Oct

  Trivia at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Fri, 12 Dec

  Winter Solstice Market

  116 S 1st Ave, Winterset, IA 50273-1907, United States
• Tue, 28 Oct

  Flannels & Flights Guys Night at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Sat, 11 Oct

  Winterset Rotary Covered Bridge Race 5K Walk/Run

  Winterset City Park
• Sat, 25 Oct

  Trick or Treat at Hy-Vee

  923 N 1st Ave, Winterset, IA 50273
• Sat, 11 Oct

  Covered Bridges Festival at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Sun, 12 Oct

  Judge Lewis House

  The Judge Lewis House Bed & Breakfast
• Sun, 12 Oct

  LIVE MUSIC @ THE HONEY LOUNGE!

  Haynes Homestead and The Honey Lounge
• Wed, 29 Oct

  All Saints & All Souls: A Family Faith Adventure

  1026 N 8th Ave, Winterset, IA, United States, Iowa 50273
• Sun, 12 Oct

  Rural Route Duo @ Winterset Cidery on Oct 12th, 2-5pm

  Winterset Cidery
• Sat, 01 Nov

  Prescribed Fire Workshop

  2508 Pammel Park Trl, Winterset, IA 50273-8308, United States
• Sat, 01 Nov

  GINGERBREAD HOUSE

  107 W Court, 50273
• Wed, 12 Nov

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

  201 W Court Ave, Winterset, IA 50273-1604, United States
• Mon, 08 Dec

  Cocoa & Photos With Santa

  122 S John Wayne Dr, Winterset, IA, United States, Iowa 50273
• Sat, 25 Oct

  Pancake Breakfast

  103 W Green St, Winterset, IA, United States, Iowa 50273
• Sat, 13 Dec

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

  Winterset Public Library
• Sun, 07 Dec

  🎄 Christmas Door Swag Workshop 🎄

  1026 N 8th Ave, Winterset, IA, United States, Iowa 50273
• Sat, 08 Nov

  Zach's 30th Hawaiian Birtdday Luau

  Redeemer Church
• Sun, 16 Nov

  Covered Bridges Winery

  Covered Bridges Winery
• 12-13 Dec

  Esther Unearthed at Winterset's Winter Solstice

  116 S 1st Ave, Winterset, Iowa