Saturday, October 14 (Tentative)

6am – 11am: Firefighters’ Pancake Breakfast Fire Station, SE of festival grounds

8:00 am — 5pm Winterset Airport — Parking and shuttle bus service to the Festival grounds available all day. They will also have antique aircraft on display, skydive demonstration at 10am and 2pm, kids’ activities, and airplane rides for $20/person. Three guests can go up in aircraft and fly over the festival grounds and Hogback Covered Bridge.

8:30 am: 15th Annual Covered Bridges of Madison County Antique Tractor Ride – Madison County Fairgrounds. Contact Curtis Saveraid 515-210-7806

8:30 am: Annual Horseshoe Tournament Registration and warm-up from 8:30 – 9:30 a.m. Pitching begins at 10:00 a.m., $10 entry fee. Madison County Fairgrounds. Sanctioned and unsanctioned members welcome. For more information, contact the Winterset Parks & Rec Department at: 515-462-3258

9:00 am: Covered Bridge Race Registration takes place between 7:45 and 8:45 am. Children’s race begins at 8:45 a.m. with the 5K Run/Walk events to begin at 9:00 a.m; starting in Winterset City Park. Sponsored by The Winterset Rotary Club. See more details and registration info here.

9am – 5pm: Festival on the Square – Over 150 vendors including arts & crafts, wineries, demonstrators, foods, entertainment stages, and more! $2 admission fee at the gate; Children 11 & under FREE. Located on the square in historic downtown Winterset

9am – 5pm: Quilt Show – Quilt boutique, vendors and demonstrators, quilt raffle. At Winterset Elementary School – Enter off 4th Avenue; $3 admission fee.

9am – 5pm: Farmers Market Southwest side of the square on 1st Avenue.

9am – 5pm: Pioneer Village – Courthouse square. See live demonstrations of crafts from the turn of the century including: spinning, weaving, jewelry making, basket weaving, woodcarving, pottery, and more!

9am – 5pm: Kidz Korner Children’s Activities – Make crafts, participate in old-fashioned games and activities, get autographs from the Wild West Cowboys, grow peanuts, take old-fashioned school lessons, go on a turtle egg hunt, play in the corn box, and more! FREE to youth. Sponsored by the Madison County Chamber of Commerce, Winterset Public Library, Winterset Art Center, Master Gardeners, Freedom for Youth Ministries, ISU Extension & Outreach, Madison County Historical Society, MCFEE, and Madison County Historical Complex.

9am – 5pmCreate a Covered Bridge by Morry Hay and Tom Clause, hosted by the Madison County Chamber. Create a replica of the Cedar Covered Bridge and learn about the unique and important construction of this Madison County icon. Located on the northwest side of the Festival grounds.

9am – 5pmAirplane Rides Over Madison County Up to 3 guests can go up in an aircraft and fly over the festival grounds and Hogback Covered Bridge. $20 per person. Also enjoy an antique aircraft display and children’s activities. Located at the Winterset Municipal Airport. 

9am – 5pm: Madison County Historical Complex “Passport To The Past” Field mercantile, penny candy sales, free horse & wagon rides, Tusha School old-fashioned school lessons by Madison County Cares, Civil War encampment with battles, Bevington-Kaser Mansion & Madison County Historical Museum tours; 815 S. 2nd Avenue. FREE admission.

9 am – 5 pm: John Wayne Birthplace Museum Tours – $15 adults, $4 seniors (60+) $8 kids (12 & under)

9 am – 5 pm: John Wayne Birthplace Trail Self-Guided Tour. Pick up maps from the John Wayne Birthplace Museum, the Madison County Chamber of Commerce, or the Madison County Historical Complex. Take a driving tour throughout Madison County to view historic locations in the life of world-famous actor, John Wayne!

9am – 5 pm: Horse & Wagon Rides View the beautiful neighborhoods in Winterset from an old-fashioned horse-drawn wagon, and step away from the bustle of the Festival for a while! Rides leave from the west side of the John Wayne Birthplace Museum; $10

9 am – 5 pm: Master Gardeners Demonstrations and lessons based on the life and work of George Washington Carver. Explore cotton plants, make peanut butter, and enjoy the park dedicated to George Washington Carver. Activities are at Carver Park, SE of festival grounds.

9 am – 5 pm: Winterset Public Library Family activities include crafts, open library time, and matching game featuring Madison County historical figures.

9 am – 5 pm: Winterset Art Center Enjoy a variety of art activities including make-and-take crafts, spin art (from 10am-2pm), quilt square art project, and outdoor demonstrations.

9 am – 5 pm: Festival Live Entertainment – 2 Music stages: Mel Penrod Stage, Benge Family Street Stage

9 am – 5 pmBras for the Cause Cast your vote for your favorite bra creation by purchasing tickets for $1 each. All proceeds stay with Bras for the Cause to fund cancer screening for Madison County residents. Located in the former American State Bank Building, 113 S. John Wayne Drive.

9 am – 5 pm: Horse and Carriage Rides by Dream Carriage, Winterset City Park. $5 per rider

10 am – Noon: Meet the Cowboys! 1880s-style cowboys and colorful outlaw characters will stroll the Festival grounds, meet Festival patrons, pose for photos, and award Sheriff’s badges Cowboys’ appearance is courtesy of Wild West Creations.

10 am – 4 pm: Courthouse Tours Meet Susan B. Anthony at the north courthouse door! Tours available at 10 am; 12 pm; and 4 pm. Sponsored by the Madison County Historical Society

10 am – 4 pm: Covered Bridge Bus Tours The Winterset Rotary Club offers daily tours (with guide) to the covered bridges.  Purchase tickets at the ticket booth on the SW side of the Festival grounds.  Buses depart from WCSD Administration Building, 110 W. Washington Street, every 20 minutes.  Tours are 2 hours in duration. $10

10 am“Patchwork Heirlooms: Care and Storage of Quilts” with Iowa Quilt Museum Curator, Virginia Berger. Additional presentations occur at 12:00 pm, 2:00 pm, and 4:00 pm

11:00 am: “The Abridged History of Quilting” with Iowa Quilt Museum President, Marianne Fons. Iowa Quilt Museum. Additional presentations occur at 1:00 pm and 3:00 pm.

Noon: High Noon Shoot Out — Madison County won’t tolerate 1880’s style lawlessness! The Old West comes alive in this battle for unclaimed territory.

1 pm – 9 pm: Winterset High School Alumni Activities:

  • Welcome Reception, Farmers & Merchants State Bank Hospitality Room, 1 – 4 pm
  • WHS All-Class Reunion Jackson Building at the Madison County Fairgrounds. 5 – 9:00 pm. Old-time photo booth, sandwiches, drinks, and fun!

2 pm – 4 pm: Meet and Greet the Cowboys and Pose for Photos! Watch as these 1880s-style cowboys recreate history through authentic cowboy appeal and action! Festival grounds.

4 pm: Civil War Skirmish at Civil War Camp at Madison County Historical Complex, 815 S. 2nd Avenue

6 pm – 9 pm: “Meet Me at the Bridge” at Winterset City Park (North Shelter). Wine tasting by Covered Bridges Winery; Picnic Meal available – Pork Loin Sandwiches, chips, & desserts; Live music by Crosswind; $10 for meal; Attendance is free.

6:45 pm: Nighttime Civil War Cannon Firing Madison County Historical Complex, 815 S. 2nd Avenue; Enjoy s’mores, a bonfire, and family fun! Bring lawn chairs or a blanket.

Sunday, October 15 (Tentative)

6:00 am – 11 am: Firefighters’ Pancake Breakfast Fire Station, SE of festival grounds

8 am – Noon: Registration for the 30th Annual Madison County Car Show. Hosted by The Central Iowa Auto Club. Judging begins at 1:30 p.m and awards presented at 3:00 p.m.; 110 West Washington Street

9 am – 2 pm: Horse and Carriage Rides by Dream Carriage. Winterset City Park. $5 per rider.

9 am – 2 pm: Horse and Wagon Rides View the beautiful neighborhoods in Winterset from an old-fashioned, horse-drawn wagon, and step away from the bustle of the Festival for a while! Rides leave from the west side of the John Wayne Birthplace Museum; $10

9 am – 5 pmFestival on the Square – Over 150 vendors including arts & crafts, wineries, demonstrators, foods, and entertainment stages. $2 admission fee at the gate; Children 11 & under FREE. Located on the square in historic downtown Winterset

9 am – 5 pm: Farmers Market Southwest side of the square on 1st Avenue

9 am – 5 pmPioneer Village Live demonstrations of crafts from the turn of the century including spinning, weaving, jewelry making, woodcarving, pottery, soap making, basket making and more! Courthouse Square

9 am – 5 pm: Kids Korner Childrens’ Activities – Make crafts, participate in old-fashioned games and activities, get autographs from the Wild West Cowboys, grow peanuts, take old-fashioned school lessons, go on a turtle egg hunt, play in the corn box, and more! FREE to youth. Sponsored by the Madison County Chamber of Commerce, Winterset Public Library, Winterset Art Center, Master Gardeners, Freedom for Youth Ministries, ISU Extension & Outreach, Madison County Historical Society, MCFEE, and Madison County Historical Complex.

9 am – 5 pm: Festival Live Entertainment – 2 Music stages: Mel Penrod Stage, Benge Family Street Stage

9am – 5pmCreate a Covered Bridge by Morry Hay and Tom Clause, hosted by the Madison County Chamber. Create a replica of the Cedar Covered Bridge and learn about the unique and important construction of this Madison County icon. Located on the northwest side of the Festival grounds

9 am – 5 pm: Madison County Historical Complex “Passport To The Past” Field mercantile, penny candy sales, free horse & wagon rides, Tusha School old-fashioned school lessons, Civil War encampment with battles, Bevington-Kaser Mansion & Madison County Historical Museum tours; 815 S. 2nd Avenue. FREE admission.

9 am – 5 pm: John Wayne Birthplace Museum Tours – $15 adults, $14 seniors (60+) $8 kids (12 & under)

9 am – 5 pm: John Wayne Birthplace Trail Self-Guided Tour. Pick up maps from the John Wayne Birthplace Museum, Take a driving tour throughout Madison County to view historic locations in the life of world-famous actor, John Wayne!

9 am – 5 pmMaster Gardeners Demonstrations and lessons based on the life and work of George Washington Carver. Explore cotton plants, make peanut butter, and enjoy the park dedicated to George Washington Carver. Activities are at Carver Park, SE of festival grounds.

9 am – 5 pm: Winterset Art Center Enjoy a variety of art activities including make-and-take crafts, quilt square art project, and outdoor demonstrations.

9 am – 5 pmBras for the Cause Cast your vote for your favorite bra creation by purchasing tickets for $1 each. All proceeds stay with Bras for the Cause to fund cancer screening for Madison County residents. Located in the former American State Bank Building, 113 S. John Wayne Drive

10 am – 11 am: Meet the Cowboys! 1880s-style cowboys and colorful outlaw characters will stroll the Festival grounds, meet festival patrons, pose for photos, and award Sheriff’s badges. Cowboys’ appearance is courtesy of Wild West Creations.

10 am – Noon: Covered Bridge Bus Tours The Winterset Rotary Club offers daily tours (with guide) to the covered bridges. Purchase tickets at the ticket booth on the SW side of the Festival grounds. Buses depart from Winterset School District Administration Building, 110 W. Washington Street, every 20 minutes. Tours are 2 hours in duration. $10

10 am – 4 pmCourthouse Tours Meet Susan B. Anthony at the north courthouse door! Tours available at 10 am; 12 pm; and 4 pm. Tours are sponsored by the Madison County Historical Society.

10 am – 4 pm: Quilt Show Quilt boutique, vendors and demonstrators, quilt raffle. At Winterset Elementary School – Enter off 4th Avenue; $3 admission fee.

10:00 am: “DIY – Barn Quilt Block Painting Demonstration” with Mark Davis. Iowa Quilt Museum

12:00 pm: Civil War Camp Skirmish at Civil War Camp at Madison County Historical Complex, 815 S. 2nd Avenue

1:00 pm: “DIY – Barn Quilt Block Painting Demonstration” with Mark Davis. Iowa Quilt Museum

2 pm: Antique Vehicle and Covered Bridge Festival Parade brought to you by the Winterset Lions Club. Lineup begins at 12:00 p.m. in the Winterset High School parking lot.

4:00 pm: Cowboys Shoot Out Madison County won’t tolerate 1880’s style lawlessness! The Old West alive in this battle for unclaimed territory. Don’t miss the Cowboys’ Shoot Out on the west side of the Festival grounds!

Schedule is Tentative / Subject to Change