Upcoming Winterset Events

Check out what's happening all around Winterset, IA

Easter Egg Hunt

 Sat, 04 Apr at 11:00 am Winterset City Park

Mother’s Day at Winterset Cidery

 Sun, 10 May at 01:00 pm 1638 Highway 169, Winterset, IA

Fly Iowa Festival 2026

Sat, 19 Sep at 02:00 pm Winterset Municipal Airport

Madison county fair truck pull 2026

 Wed, 15 Jul at 07:00 pm Madison County Fairgrounds

Blues & BBQ Dinner

Sat, 11 Apr at 06:00 pm 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Live Music at Winterset Cidery 5.23.26

 Sat, 23 May at 01:00 pm 1638 Highway 169, Winterset, IA

Winterset Cidery Season Opening

 Sat, 11 Apr at 01:00 pm 1638 Highway 169, Winterset, IA

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

 Sat, 18 Apr at 10:00 am 231 N 2nd Ave, Winterset, IA, United States, Iowa 50273

Live Music at Winterset Cidery 5.24.26

 Sun, 24 May at 01:00 pm 1638 Highway 169, Winterset, IA

BINGO!

 Tue, 07 Apr at 05:00 pm Madison County Fair, Iowa

Early Mother's Day Paint & Sip at Winterset Cidery!

 Thu, 07 May at 06:00 pm Winterset Cidery

Ladies Night at Winterset Cidery

 Tue, 21 Apr at 05:00 pm 1638 Highway 169, Winterset, IA

Fridays at The Farm

Fri, 19 Jun at 05:00 pm 1578 North River Trail, Winterset, IA

Easter Sunday Service

 Sun, 05 Apr at 10:00 am 224 E Court Ave, Winterset, IA, United States, Iowa 50273

Scratch Pizza Night on the Farm

Fri, 26 Jun at 05:00 pm 1578 North River Trail, Winterset, IA

Trivia Thursday at Winterset Cidery

 Thu, 09 Apr at 05:00 pm 1638 Highway 169, Winterset, IA

Middle River Arts Festival

 Sat, 02 May at 10:00 am 2508 Pammel Park Trl, Winterset, IA 50273-8308, United States

Sourdough Workshop at Winterset Cidery

 Fri, 10 Apr at 06:30 pm 1638 Highway 169, Winterset, IA

Live Music at Winterset Cidery 4.18.26

 Sat, 18 Apr at 01:00 pm 1638 Highway 169, Winterset, IA

Easter Brunch 🐰

 Sun, 05 Apr at 08:00 am 923 N 1st Ave, Winterset, IA 50273

A Picnic in the Forest

 Sat, 09 May at 05:30 pm Iris Aisle USD 150 to 287

Winterset Porchfest 2026

 Sun, 30 Aug at 11:00 am Winterset, Iowa

Jake Schrodt at Winterset Cidery

 Sat, 11 Apr at 05:00 pm Winterset Cidery

Saturday Morning Breakfast

 Sat, 18 Apr at 08:00 am 111 s 1st Ave, Winterset, IA

Covered Bridge Winery

 Sat, 30 May at 06:30 pm Covered Bridges Winery

Live Music at Winterset Cidery

 Sun, 31 May at 01:00 pm 1638 Highway 169, Winterset, IA

Live Music at Winterset Cidery 5.17.26

 Sun, 17 May at 01:00 pm 1638 Highway 169, Winterset, IA

Live Music at Winterset Cidery 5.2.26

 Sat, 02 May at 01:00 pm 1638 Highway 169, Winterset, IA

Sunday Funday

Sun, 12 Apr at 02:00 pm Winterset Cidery

Paint Madison County - A Plein Air Festival

 Sun, 14 Jun at 09:00 am 73 Jefferson Street, Winterset, IA, United States, Iowa 50273

RetroSpect at Covered Bridges Winery

 Sat, 18 Jul at 07:00 pm Covered Bridges Winery

Sourdough Starter Class

Tue, 14 Apr at 06:30 pm 111 s 1st Ave, Winterset, IA, United States, Iowa 50273

Fridays at The Farm

Fri, 17 Jul at 05:00 pm 1578 North River Trail, Winterset, IA

Bunco Night

 Sat, 18 Apr at 06:00 pm 1026 N 8th Ave, Winterset, IA, United States, Iowa 50273

Pies & Pours with Kevin Fifo

Fri, 10 Jul at 06:00 pm 1578 North River Trail, Winterset, IA

Good Friday Service

 Fri, 03 Apr at 06:30 pm 224 E Court Ave, Winterset, IA, United States, Iowa 50273

Live Music at Winterset Cidery 4.19.26

 Sun, 19 Apr at 01:00 pm 1638 Highway 169, Winterset, IA

Winterset Wine Walk

Sat, 09 May at 01:00 pm 73 Jefferson Street, Winterset, IA, United States, Iowa 50273

Tribal Muse Annual Spring Workshop

 Sat, 18 Apr at 09:00 am Madison County Fairgrounds

Moors & McCumber / Sunday Wine Down

 Sun, 19 Apr at 02:00 pm 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Garden Post Class

 Sun, 19 Apr at 01:00 pm 115 W. Jefferson Street, Winterset, IA

Opening Day @ Speckled Hen Farms

Sat, 23 May at 11:00 am 1578 North River Trail, Winterset, IA

Fly Fishing Class with Marty McVey

 Sun, 26 Apr at 11:00 am 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Pancake Breakfast

 Sat, 11 Apr at 07:00 am Winterset American Legion

Speckled Hen Farms

 Sun, 27 Sep at 03:00 pm Speckled Hen Farms Iowa

2026 Tourism Kickoff Breakfast!

 Thu, 09 Apr at 07:30 am Francis and Thelma Jackson Building

Winterset High School Mattress Fundraiser

 Sat, 11 Apr at 10:00 am Winterset Senior High School

2026 May Meeting

 Wed, 27 May at 11:00 am Allendan Seed Company

Vendor Meeting

 Sat, 04 Apr at 09:00 am The Warehouse on 2nd

Carter Booth's High School Grad Party

 Sun, 17 May at 01:00 pm Union State Bank