All Upcoming events

• Sat, 04 Apr, 2026 - 11:00 AM

  Easter Egg Hunt

  Winterset City Park
• Sat, 19 Sep, 2026 - 02:00 PM

  Fly Iowa Festival 2026

  Winterset Municipal Airport

  1536+ Interested
• Sun, 29 Mar, 2026 - 02:00 PM

  WINTERSET, IA - Aaron Simmons LIVE at Covered Bridges Winery

  Covered Bridges Winery
• Wed, 15 Jul, 2026 - 07:00 PM

  Madison county fair truck pull 2026

  Madison County Fairgrounds

  148+ Interested
• Sat, 11 Apr, 2026 - 06:00 PM

  Blues & BBQ Dinner

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

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

  Decades on the Orchard

  Winterset Cidery

  196+ Interested
• Sat, 11 Apr, 2026 - 01:00 PM

  Winterset Cidery Season Opening

  1638 Highway 169, Winterset, IA

  78+ Interested
• Sat, 18 Apr, 2026 - 10:00 AM

  RUNWAY ON 2ND: Sip. See spring trends. Shop the square.

  231 N 2nd Ave, Winterset, IA, United States, Iowa 50273

  64+ Interested
• Sat, 28 Mar, 2026 - 03:00 PM

  Easter Fest

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

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

  Aaron Simmons / Sunday Wine Down

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

  33+ Interested
• Sat, 14 Mar, 2026 - 08:00 AM

  March 14th Farmers Market

  The Warehouse on 2nd

  1205+ Interested
• Fri, 20 Mar, 2026 - 05:00 PM

  Winterset Cidery BBQ Invasion

  Winterset Cidery

  30+ Interested
• Tue, 21 Apr, 2026 - 05:00 PM

  Ladies Night at Winterset Cidery

  1638 Highway 169, Winterset, IA
• Fri, 26 Jun, 2026 - 05:00 PM

  Scratch Pizza Night on the Farm

  1578 North River Trail, Winterset, IA

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

  Looking4Luke/ Music at the Winery

  Covered Bridges Winery

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

  A Picnic in the Forest

  Iris Aisle

  USD 150
• Sat, 14 Mar, 2026 - 06:00 PM

  MC Line @ The Honey Lounge

  The Honey Lounge by Haynes Homestead

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

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

  Big Rack Brew Haus

  67+ Interested
• Sat, 18 Apr, 2026 - 01:00 PM

  Live Music at Winterset Cidery 4.18.26

  1638 Highway 169, Winterset, IA

  98+ Interested
• Sun, 30 Aug, 2026 - 11:00 AM

  Winterset Porchfest 2026

  Winterset, Iowa

  310+ Interested
• Sat, 18 Apr, 2026 - 08:00 AM

  Saturday Morning Breakfast

  111 s 1st Ave, Winterset, IA

  37+ Interested
• Sat, 11 Apr, 2026 - 05:00 PM

  Jake Schrodt at Winterset Cidery

  Winterset Cidery

  65+ Interested
• Tue, 17 Mar, 2026 - 10:00 AM

  Get your Green On!

  224 S John Wayne Dr, Winterset, IA

  15+ Interested
• Sat, 30 May, 2026 - 06:30 PM

  Covered Bridge Winery

  Covered Bridges Winery

  18+ Interested
• Sat, 14 Mar, 2026 - 08:00 AM

  Hunter Education Field Day

  Madison County Sportsman Gun Club

  6+ Interested
• Fri, 20 Mar, 2026 - 06:00 PM

  Ceramic Charcuterie Board Class

  224 S John Wayne Dr, Winterset, IA

  51+ Interested
• Sat, 18 Jul, 2026 - 07:00 PM

  RetroSpect at Covered Bridges Winery

  Covered Bridges Winery

  72+ Interested
• Sun, 14 Jun, 2026 - 09:00 AM

  Paint Madison County - A Plein Air Festival

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

  65+ Interested
• Sun, 22 Mar, 2026 - 01:00 PM

  Hoops & Hops at Winterset Cidery

  1638 Highway 169, Winterset, IA

  96+ Interested
• Sat, 04 Apr, 2026 - 02:30 PM

  Snow Trillium Tour

  Winterset Public Library

  6+ Interested
• Sun, 12 Apr, 2026 - 02:00 PM

  Sunday Funday

  Winterset Cidery
• Fri, 19 Jun, 2026 - 05:00 PM

  Fridays at The Farm

  1578 North River Trail, Winterset, IA

  14+ Interested
• Sun, 19 Apr, 2026 - 01:00 PM

  Live Music at Winterset Cidery 4.19.26

  1638 Highway 169, Winterset, IA

  19+ Interested
• Fri, 10 Jul, 2026 - 06:00 PM

  Pies & Pours with Kevin Fifo

  1578 North River Trail, Winterset, IA

  9+ Interested
• Sat, 28 Mar, 2026 - 08:00 AM

  NASA Iowa State

  Winterset Junior High

  29+ Interested
• Fri, 03 Apr, 2026 - 06:30 PM

  Good Friday Service

  224 E Court Ave, Winterset, IA, United States, Iowa 50273

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

  Barn Quilt Class

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

  6+ Interested
• Sat, 18 Apr, 2026 - 06:00 PM

  Bunco Night

  1026 N 8th Ave, Winterset, IA, United States, Iowa 50273
• Wed, 25 Mar, 2026 - 06:00 PM

  Pond Management 101

  Madison County Conservation Center

  31+ Interested
• Tue, 31 Mar, 2026 - 06:00 PM

  Madison County's Most Wanted

  2508 Pammel Park Trl, Winterset, IA 50273-8308, United States

  9+ Interested
• Sat, 14 Mar, 2026 - 10:00 AM

  Book Signing Event by Terri Stephens-Higgins @ Quest Haven Books & Comics - Winterset, Iowa

  Quest Haven Books & Comics

  40+ Interested
• Fri, 20 Mar, 2026 - 06:30 PM

  Liv @ The Honey Lounge

  The Honey Lounge by Haynes Homestead

  7+ Interested
• Sun, 22 Mar, 2026 - 03:00 PM

  Spring Training for Minors & Majors Baseball

  Triple Play Training & Events

  10+ Interested
• Sat, 21 Mar, 2026 - 07:00 AM

  Pancake Breakfast

  103 W Green St, Winterset, IA, United States, Iowa 50273

  6+ Interested
• Sun, 29 Mar, 2026 - 01:00 PM

  Spring Kick Off

  Winterset High School

  39+ Interested