Upcoming Winterset Events

Check out what's happening all around Winterset, IA

Ladies Night at Winterset Cidery

Tue, 07 Oct at 05:00 pm 1638 Highway 169, Winterset, IA

Self-Help International Farm to Table Dinner with Chef Katie Porter

Sun, 14 Sep at 06:00 pm 1640 Hwy 169, Winterset, IA 50273

Friday Night Magic!

Fri, 19 Sep at 05:00 pm 104 N. 1st Avenue, Winterset, IA, United States, Iowa 50273

Fridays at The Farm

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

Seasonal Cider Release at Winterset Cidery

Sat, 20 Sep at 01:00 pm 1638 Highway 169, Winterset, IA

Ladies Bunco Night

Sat, 04 Oct at 06:00 pm 1026 N 8th Ave, Winterset, IA, United States, Iowa 50273

Scratch Pizza Night on the Farm

Fri, 26 Sep at 05:30 pm 1578 North River Trail, Winterset, IA

Fall Crawl at Winterset Cidery

Sun, 28 Sep at 10:00 am 1638 Highway 169, Winterset, IA

Nashville Style Listening Event

Sat, 25 Oct at 06:30 pm 2207 170th Drive, Winterset, IA, United States, Iowa 50273

21+ Jingle Jammie Jam

Sat, 29 Nov at 07:00 pm 111 s 1st Ave, Winterset, IA

Live Music at Winterset Cidery

Sat, 04 Oct at 05:00 pm 1638 Highway 169, Winterset, IA

Mad Co Fall Crawl - Iris Aisle

Sun, 28 Sep at 12:00 pm 2352 Holliwell Bridge Rd, Winterset, IA, United States, Iowa 50273

Willie Mac & The Lost Cousins / Music at the Winery

Sat, 18 Oct at 06:30 pm Covered Bridges Winery

Fresh Fall Market - Grand Opening!

Fri, 12 Sep at 09:00 am 124 N. 1st Ave, Winterset, IA

Hold Our Youth Tight Poker Run

Sat, 20 Sep at 11:00 am Winterset Cidery

Post Prom Meeting

Sun, 14 Sep at 06:30 pm 720 Husky Drive

Pumpkin Palooza

Sat, 04 Oct at 10:00 am 1578 North River Trail, Winterset, IA

Devon Miller / Sunday Wine Down

Sun, 28 Sep at 02:00 pm 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Dungeons & Dragons Night!

Wed, 17 Sep at 05:00 pm 104 N. 1st Avenue, Winterset, IA, United States, Iowa 50273

3-Day Estate Moving Auction | Estate of Leona & the late Pete Jackson

Fri, 12 Sep at 04:00 pm 113 S 1st Ave, Winterset, IA, United States, Iowa 50273

Live Music at Winterset Cidery

Sun, 21 Sep at 02:00 pm 1638 Highway 169, Winterset, IA

Family Fishing Tournament!!

Sat, 20 Sep at 05:00 am 1305 W Jefferson St, Winterset, IA, United States, Iowa 50273

Dahlia Field Day at PepperHarrow

Sun, 21 Sep at 12:00 pm PepperHarrow

Bi-Weekly Trivia @ The Honey Lounge

Thu, 09 Oct at 06:30 pm 111 s 1st Ave, Winterset, IA

Cake Decorating Class: 101 (at Winterset Cidery)

Sun, 05 Oct at 02:00 pm Winterset Cidery

Trivia at Winterset Cidery

Thu, 25 Sep at 05:00 pm 1638 Highway 169, Winterset, IA

Biscuit Bliss Breakfast

Sun, 21 Sep at 09:00 am 111 s 1st Ave, Winterset, IA

Madison County Covered Bridge Festival

Sat, 11 Oct at 09:00 am 73 Jefferson Street, Winterset, IA, United States, Iowa 50273

Live Music at Winterset Cidery

Sun, 14 Sep at 02:00 pm 1638 Highway 169, Winterset, IA

AUCTION: ANTIQUES; STONEWARE; POTTERY

Sun, 14 Sep at 12:00 pm 914 N 1st Avenue • Winterset, Iowa

Duke It Out Chili Cook-Off

Sat, 20 Sep at 12:00 pm 101 E Jefferson St, Winterset, IA, United States, Iowa

Madison County Fall Crawl

Sun, 28 Sep at 10:00 am Covered Bridges Winery

4th Annual “Duke It Out Chili Cook Off”!

Sat, 20 Sep at 12:00 pm 101 E. Jefferson St., Winterset, Iowa

LILL Permanent Jewelry at Madison County Fall Crawl

Sun, 28 Sep at 10:00 am Madison County Fall Crawl

Speaking of Art: Painting

Mon, 29 Sep at 06:00 pm Winterset Public Library

Fuel Up & Save Event - Winterset FAST STOP

Wed, 17 Sep at 04:00 pm 1214 N 4th Ave, Winterset, IA 50273, United States

Live Music at Winterset Cidery

Sat, 27 Sep at 05:00 pm 1638 Highway 169, Winterset, IA

PIEOWA Documentary - Iowa Theatre

Sun, 05 Oct at 02:30 pm Iowa Theatre

Holiday Market on The Farm 2025

Sat, 08 Nov at 10:00 am 1578 North River Trail, Winterset, IA

Judge Lewis House

Sun, 12 Oct at 05:00 pm The Judge Lewis House Bed & Breakfast

Casey Peasley at Winterset Cidery

Sat, 04 Oct at 05:00 pm Winterset Cidery

Taco de Septiembre

Mon, 29 Sep at 05:00 pm 111 s 1st Ave, Winterset, IA

New Comic Book Day!

Wed, 17 Sep at 10:00 am 104 N. 1st Avenue, Winterset, IA, United States, Iowa 50273

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

Sun, 12 Oct at 02:00 pm Winterset Cidery

Speckled Hen Farms

Sun, 28 Sep at 03:00 pm Speckled Hen Farms Iowa

Stitch In the Museum

Thu, 09 Oct at 10:00 am 68 E Court Ave , Winterset, IA, United States, Iowa 50273

15th Annual Healthiest State Walk

Wed, 01 Oct at 12:00 pm Madison County Courthouse

Second Annual Tony Webb Memorial Ride

Sat, 20 Sep at 10:00 am 2617 Cumming Road, Winterset, IA

Paint Madison County: A Plein Air Festival

Sun, 21 Sep at 09:00 am 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Winterset Rotary Covered Bridge Race 5K Walk/Run

Sat, 11 Oct at 09:00 am Winterset City Park

Winter Solstice Market

Fri, 12 Dec at 06:00 pm 116 S 1st Ave, Winterset, IA 50273-1907, United States

MomCo Winterset

Sat, 04 Oct at 09:00 am New Bridge Church

2025 MVC Meeting

Sat, 27 Sep at 08:00 am 2172 245th Lane, Winterset, IA

Madison County's Most Wanted: Kick-off

Sat, 08 Nov at 10:00 am 2508 Pammel Park Trl, Winterset, IA 50273-8308, United States

Covered Bridges Winery

Sun, 16 Nov at 02:00 pm Covered Bridges Winery

Church Clean/Work Day

Sat, 04 Oct at 08:00 am 418 W. Summit St. , Winterset, IA, United States, Iowa 50273

BINGO

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

Amazing Scavenger Hunt! - Winterset Whimsical Wander

Tue, 26 Nov at 08:00 am 504 W Jefferson St USD 15

Madison County Historical Society Car Show in Memory of Ken Burk

Sat, 20 Sep at 10:00 am Madison County Historical Complex

Dirty Soda Sampling Event

Fri, 19 Sep at 04:00 pm 923 N 1st Ave, Winterset, IA 50273

Dog Days @ the Winery/ IOWA Services Dogs Fundraiser

Sun, 05 Oct at 12:00 pm 2207 170th Drive, Winterset, IA, United States, Iowa 50273

Friday Fun Nights

Fri, 19 Sep at 05:00 pm 231 N 2nd Ave, Winterset, IA, United States, Iowa 50273

Esther Unearthed at Winterset's Winter Solstice

Fri, 12 Dec at 09:00 am 116 S 1st Ave, Winterset, Iowa

Lean Into The Light: New Watercolors By Christine Hilbert

Sat, 18 Oct at 01:00 pm The Warehouse on 2nd

UTurn Youth Group – Connecting, Growing, and Having Fun

Wed, 17 Sep at 05:30 pm 224 E Court Ave, Winterset, IA, United States, Iowa 50273

Categories

Popular topics