Programs & Activities

Spring 2019

Baseball Clinic

Boys grades 3rd – 8th
Fee $15.00
Held in early March after school at the Hitting Facility / Elementary Gym
Includes an accuracy and speed contest on the last day.
Instruction provided by the varsity baseball coaching staff.
Registration ends Feb. 15.

Easter Egg Hunt in City Park

City Park North Shelter Saturday, April 20, 2019, 11:00 am.
Boys and girls up to 9 years old.
The Easter Bunny will be present. Sponsored by Madison County Realty.

A Walk in the Park

Enjoy the fresh air and natural beauty at City Park.
Every mile walked / run by a sedentary person gives him / her an extra 21 minutes of life.
For a longer distance and a little more rugged terrain hike to Clark Tower – 2 miles. Trail maps are available.

Celebrate Earth Day 2019

All ages, no fee
Sunday, April 28th
Meet at City Park south shelter between at 1:00 pm for an interpretative walk to Clark Tower and back.
Please join others to enjoy the community of the woodlands. Volunteers with the organization For Lands Sake will lead the walk and give a brief discussion on our forests.

Adult Softball: Two leagues offered
1) Adult Coed (5 men and 5 women). Fee $250. Tuesday and Thursday evenings, May 8- July 21. Must be at least 18 and out of high school.
2) Coed Church (at least 3 women). Fee $125. Monday evenings May 7-June 11. Team members must be church members. All games are played at MM Fields Softball Complex. Anyone interested in forming a new team should contact the WPRD. Registration ends April 20.

Adult Tennis
Adult men and women, Fee $10. Beginning in April a men’s and women’s Tennis Drop-in League is planned. Courts will be reserved for a couple hours one day per week for each league. Also, with enough interest a “tennis ladder” league for singles or doubles could be scheduled. To register or to provide feedback contact WPRD at 462-3258 or email

Intro to Pickleball

All ages, no fee
Learn rules, techniques and how to play the game or pickleball.
Pickleball is a game for all ages.
Join us on Saturday, April 27th 10:00 am at the City Tennis Courts for a fun and instructional session then stay and play a game or two.
A few paddles and balls will be provided. Registration is required and ends April 19.


Adult men and coed
Fee $10
Men Sunday evenings at 7:00 pm
Coed Tuesday evenings at 7:00 pm
Beginning in May, a men’s and women’s Pickleball Drop in League is planned. Courts will be reserved on Tuesday nights. Don’t have your own paddles/ balls? Paddles and balls are available for check out thru the Winterset Library. To register email

Senior Pickleball

65 + men and women
Fee $10
Beginning in May a senior men’s and women’s Pickleball Drop in league is planned. Courts will be reserved on Tuesday mornings. Don’t have your own paddles/ balls? Paddles and balls are available for check out thru the Winterset Library. To register contact the WPRD at 462-3258 or email

Madison County Open Horseshoes

Sat., May 11
Fee $10.00
Register and warm up 8:30 – 9:30 am.
Pitching begins at 10:00 am.
Madison County Fairgrounds.
Sanctioned by Iowa Hawkeye Horseshoe Pitchers Association. Divisions are determined by ringer percentages. Non members of IHHPA will compete in an open division. Sanctioned tournament also held July 21 & October 12. Contact person: John Ridgely (515) 779-8816 or Rick Hudson (515) 537-5522.

Live Healthy Iowa Kids Track Championships

Friday, May 24 at the high school track.
Held in conjuction with the Winterset Middle School field day.
Specific information and registration forms will be handed out at school.
Top finishers of the meet advance to the State meet held June 22 in Marshalltown.
Rain make up is Tuesday, May 28.  No-fee.

John Wayne 5K Run/Walk

Saturday, May 25th 9:00 AM.
Sponsored by Winterset Rotary Club & Mad. Co. Health Care Systems.
Pre-registration encouraged.
Fees before May 1: $25.00
After April 30: $30.00
Day of Race: $35.00
Fourteen age divisions offered  with medals.
Benefits CRISP, Wildwood Hills Ranch & Healthy Kids Initiative.
Register on-line at or see or contact Bob Kaldenberg at 515-462-4731,
Forms also available at City Hall.

Youth Spring Tennis Fun
Boys and girls grades 2, 3, 4
Fee $15.00
Tues and Thurs 3:30 – 4:30, May 7, 9, 14 & 16 at City Tennis Courts.
Basic skills are taught using fun drills and tennis games.
Balls and racquets are provided.
Registration ends May 3.

Introduction to Bocce Ball

All ages, no fee
Saturday, May 18, 10:00 am
Arbor Shelter in City Park
Have you heard of Bocce Ball? Did you know we have Bocce Ball Courts in our City Park? Join us and learn about this fun game. Learn the rules and strategies of playing Bocce Ball. Mayor Olson will provide instruction. Equipment provided.
Registration is required and ends May 13.

Summer 2019

Mayor’s Bike Ride

Excellent for all age groups children to seniors.
Saturday, June 1st
No Fee
Check in at 8:00 am parking lot of the Winterset Aquatic Center.
This leisurely ride will be to City Park and back.
Purpose: to bring awareness for the need of a biking/jogging/walking trail.
Assisting with the ride will be the Winterset Police Department, Winterset Optimist Club and the WPRD.
Kids and Seniors (65+) wearing a helmet receive a certificate for a free ice cream cone.

2019 “First Friday” Concert Series at City Park

Concert series is held at the North Shelter area on three Friday evenings, June 7, July 5, Aug. 2
Beginning at 6:00 pm – Food & favorite beverage served.
7:00 – 10:00 pm – Live Music
There is no admission charge for the concert series.
No carry-in beverages or food allowed.
Watch for further information.
Sponsored by Madison Co. Chamber & WPRD

B.R.A.T. – Bike Ride Around Town

For all ages on Friday evenings June 7, July 5 and August 2.
Join us for a bike ride before the Concert Series at City Park.
Riders will begin leaving City Park at 5:00 and ride the SHARROWS around Winterset.
(Maps of the shared road way route will be provided).
Route is 7 miles and you are welcome to ride it as many times as you would like.
After your ride head to the North Shelter for food and live music.

Youth Blastball

Girls & boys ages 3 & 4 (age determined on September 15, 2019).
Beginning baseball / softball game.
Held at MM Fields – Softball Complex.
Wednesdays June 5, 12, 19 & 26.
Girls  9:00-9:45 am
Boys 10:00 – 10:45 am.
Fee $15.00
Registration ends May 24.

Youth T-Ball

Girls & boys ages 5 & 6 (age determined on September 15, 2019).
Youth develop beginning fundamentals of baseball /softball.
Held at MM Fields – Softball Complex with two evening games held at Giffin Fields.
Fee is $20 per child.
Registration ends May 24.


Tuesday / Thursday -June 4, 6, 11, 13, 18
Age 5  – 9:00 – 10:00 am         Fee $20.00
Age 6  – 10:15 – 11:15 am       Fee $20.00


Thursday –  June 20    6:00 or 7:00 pm
Thursday  –  June 27   6:00 or 7:00 pm

Little Legends Golf Lessons

Boys/girls K thru 6th  (18 – 19 yr).
June 10 thru the 14th at Lakeview Country Club.
K, 1 , 2, 3        9:00 – 10:00 am.          Fee $50.00
4, 5, 6             10:00 – 11:00 am.        Fee $50.00

Golf clubs, balls, instruction and other equipment is provided. Registration forms are available at the schools and the WPRD.
Make checks payable to Little Legends Golf.
Contact Brett West with questions, 515-577-7910.

Winterset Youth Golf Tourney

Boys/ girls K – 6 (18/19 school yr)
Fri. June 14 at Lakeview Country Club
Check-in 8:30am / golf at 9:00.
Fee $15.00
Event includes putting/chipping contest, hole prizes, adjusted golf format.
Adult volunteers needed.
Co-sponsored by WHS golf program, Winterset Optmist Club, Lakeview Country Club and the WPRD.
Event included with Little Legends Golf Lessons.
Registration ends June 4.

Movie Night in the Park

All ages, no fee
Saturday,  June 22 – approximately 9 pm at North Shelter.
Family fun with a movie in the park.
Bring your own lawn chair or blanket.
Movie co-sponsored by Madison County Realty and the WPRD.

Playground in the Park

Boys and girls ages 3 thru 8
South Shelter Winterset City Park

M, T, W, TH  10:00 – Noon

Playground I:       June 24 – 27           Fee $30.00
Playground II:     July 29 – Aug 1      Fee $30.00
Playground III:    August 12 – 15        Fee $30.00

Program includes crafts, stories, hikes, games, snacks and playground.
One of the highlights is a group hike to Clark Tower on last day – sack lunch needed on this day.
Registration ends June 8. 

Youth Tennis Lessons

Session I– beginner, grades 3, 4, 5, 6.
M-Th July 8-11 8:45 – 9:45 am.
Fee $15.00

Session II– advance beginner, grades 3, 4, 5, 6.
M-Th  July 8-11 10:00-11:00 am.
Fee $15.00

Session III– intermediate, grades 5, 6, 7, 8.
M -Th  July 15 – 18  8:30 – 9:30 am.
Fee $15.00

Balls, racquets and instruction provided. Lessons held at city tennis courts.
Pre-register at least 1 week in advance.

Winterset Tennis Rally

Boys / girls grades 2 – 6
Friday, July 19, 10:00 am – 1:00 pm at the City Tennis Courts.
Fun filled day of tennis, games and contests.
Prizes awarded. Balls, racquets and supervision provided.
All skill levels welcome.
Bring a sack lunch and your swim suit.
Free swimming at the aquatic center following the rally.
Call or email to register.
No Fee.

Madison County Fair Horseshoes

Sun., July 21
Fee $10.00
Register and warm up 8:30 – 9:30 am.
Pitching begins at 10:00 am.
Madison County Fairgrounds.
Sanctioned by Iowa Hawkeye Horseshoe Pitchers Association Divisions are determined by ringer percentages.
Non members of IHHPA will  compete in an open division.
Sanctioned tournament also held October 12.
Contact person:  Chris Jordan (515) 669-3085

Winterset RAGBRAI

Join in the many fun activities and entertainment that will be held on the uptown square for the RAGBRAI overnight stay in Winterset on Monday, July 22.
Details will be found at as they develop.

Junior Police and Fire Academies

Boys & girls grades 4, 5, 6 (2019/20)
Fee $20.00
July 31 & August 1
Jr. Police 8:00 – 10:00 am at Winterset Library
Jr. Fire 10:00 am – Noon at the Fire Station
The Winterset Junior Police and Fire Academy is an opportunity for kids to learn about police and fire training and related topics and is presented by officers of the Winterset Police Depart and Winterset Fire Department. Cadets will experience activities including: physical agility training, fingerprinting, evidence collection, a K-9 demonstration, fire safety, fire fighting techniques and equipment and other activities. Cadets will receive a Winterset Junior Police Academy t-shirt.
Class size: 16.
Registration ends July 19.

Annual Cannonball Pump and Run

Saturday August 3
Fees $25 / $30 / $35
Check in 6:30 – 7:00 am
Lifting starts at 7 am
5K at 8:30 am
Cannonball Park  – 201 W. Court Ave.
Fifteen age divisions offered w/medals.
Proceeds go to Winterset Rotary Scholarship fund & WHS Activity Fund.
Register on line at
Fliers available at City Hall.
Questions Contact Bob Kaldenberg 515-462-4731 or
Sponsored by Winterset Rotary club.

Fall 2019

Youth Fall Tennis Fun

Boys and girls grades 2, 3, 4
Fee $15.00
Tues & Thurs. 3:30 – 4:30
August 20, 22, 27 & 29 at City Tennis Courts
Basic skills are taught using fun drills and tennis games.
Balls and racquets are provided.
Registration ends August 17.

Youth Flag Football

Boys and girls grades 2, 3, 4
Fee $20.00
2019-20 school year
August 26 – mid October
Martin Marietta Fields-Softball Complex
Participants are divided into teams with adult volunteer coaches. If YOU are interested in coaching, contact the WPRD. Games held primarily Monday evenings, practices determined by coaches.
Registration ends 8/16

Bocce Ball Tournament

Saturday, September 7
4:00 pm
Winterset City Park Arbor Shelter
Trophies to the winners.
Dinner at 5 pm by Cattlemen.
All two person teams must be registered by 4 pm to be placed in a round robin bracket.
Fee:  $50 per team. A
ll proceeds go to local non-profits.
Sponsored by The Winterset Rotary Club
Contact Person: Sarah Simon 515-577-6155,

Girls Instructional Volleyball

Girls grades 5th& 6th
Fee  $20.00
Tuesday and Thursday Sept. 10 – Oct. 17
at Elementary Gym
Program teaches fundamentals and provides an opportunity to play organized games.
Registration ends September 6.

Junior High Introduction to Horseshoes

This program is a part of the 7th & 8th grade Physical Education curriculum. During P.E. classes in September, students learn about the game of horseshoes and have an opportunity to pitch several shoes.  Instructions, horseshoes and court preparations are provided by the WPRD.

Covered Bridge Horseshoe Tournament

Sat., Oct. 12
Fee $10.00
Register and warm up 8:30 – 9:30 am.
Pitching begins at 10:00 am
Madison County Fairgrounds.
Sanctioned by Iowa Hawkeye Horseshoe Pitchers Association
Sanctioned divisions are determined by ringer percentages.
Non members of IHHPA will compete in an open division.
Contact person: John Pletchette (515) 462-3258

Halloween Trick or Treat Night

3:30 – 5:00 pm on the square
5:00 – 7:00 pm in the community
Keep in mind:
*dress children in bright clothing, carry a blinking flashlight or other noticeable device
*Be careful with full facial masks so not to block line of sight
*Parents assist little-ones
*Drivers follow all traffic signs, drive slowly, look out for  ghouls!

For all ages!! Don’t let the weather stop you from walking. Indoor walking is available at Hy-Vee during their business hours as well as at the Junior High Gym from 5:00 to 6:00 pm.

Women’s Volleyball League

Women 18 & older / out of HS
Fee $125
Wednesday evenings Sept. 4 – Nov. 6
Junior High Gym.
Two divisions of play offered.
New teams are always welcome.
Registration ends August 23.

Annual Covered Bridge Race 4K & 8K Run/Walk

Saturday Oct. 12 at Winterset City Park
Early registration fees before October 1st:
9:00 am        4K/8K run/walk       Fee $25
8:45 am         Children’s Race        Fee $15
Thirteen age divisions offered with medals.
Sponsored by the Winterset Rotary Club for the benefit of the City Park Maze.
Register on line at  or for flyer and paper registration.
Questions contact Bob Kaldenberg at 515-462-4731 or

Slime Time

Boys & girls grades K – 4th
Fee $15
Saturday, October 19
1:00 – 3:00 pm
Put on some old clothes and join us in the Library meeting room for a slimy good time.
Be ready to get messy.
We will make all kinds of slime, goo and glop.
Snack provided. Registration ends October 4

Kids in the Kitchen

Boys & girls grades K – 3rd
Fee $30
Saturdays, Oct. 26, Nov. 2, 9, 16
K & 1st, 1:00 – 2:00 pm
2nd & 3rd, 2:00 – 3:00 pm
Winterset Library meeting room
Kids in the kitchen in an introduction to cooking for young boys and girls.
Students will be taught everything from mixing, measuring to kitchen safety.
Each class the children will make a snack while learning kitchen basics and cooking techniques.
Please feel free to bring an apron to protect clothing from any kitchen messes.

Winter 2019/20

Turkey Toss

Saturday, November 23
No fee
9:00 am – Noon
Junior High School Gym
Child / parent form a team to compete in a free throw shooting contest .
Three age groups for boys / girls: 3 – 5 grade, 6 – 8 grade and high school.
High score in each age group wins a free turkey.

Adult Basketball Open Gym

Adults 18 & older out of high school
No Fee
Wednesdays, Nov. 6 – April 1, 2020
6:45 – 9:00 pm
High School gym
For more information contact the WPRD

Indoor Pickleball

Adult men and women
Fee $10
Beginning in November a men’s and women’s Pickleball Drop in League is planned.
Courts will be set up on Sunday nights in the Elementary gym.
Women will play from 4:00 – 5:30 with Men to follow from 6:00 – 7:30 pm.
Don’t have your own paddles/ balls?  Paddles and balls are available for check out thru the Winterset Library.
To register contact the WPRD at 462-3258 or email

Notes from the North Pole

All boys and girls
No fee
Register child by December 6 to receive a letter from Santa.
Letters mailed directly to your child with Santa’s name and return address on the envelope.
Unique idea for all your nieces, nephews or grandchildren.
Register at the WPRD office or call 515-462-3258.

Youth Basketball

Boys and girls grades 2 thru 6
Fee $20.00
December 7 thru January 25
Jr High & Elementary gyms
Designed to teach proper fundamentals, have fun with friends and play games.
Volunteer coaches guide teams.
If you are interested in coaching contact the WPRD.
Registration ends November 18.

Adult Co-Ed Volleyball Leagues

Men /Women 18 yrs & out of high school
Wednesday evenings
Fee $125.00
January 29 thru April 8, 2020
Junior High Gym
Season begins in late January with tourney finals played in April.
Three men and three women make up a team.
Captains meeting is scheduled for Wednesday, January 22, 2020.
Registration ends January 17, 2020.

Father Daughter Sweetheart Dance

Girls grades K – 4th
Fee $30.00 / couple
$10.00 additional daughter
Friday, February 7,  2020, 6:30 – 9 pm at the Jackson Building.
Fathers and Daughters, grandfathers and granddaughters, uncles and nieces are all invited to for an evening of music, dancing and fun.
A local photographer will be on hand to take your picture at an additional charge.
Registration ends Jan. 17, 2020.
Limited to 150 young ladies.

Mother/Son Nerf War

Boys grades K – 6th
Fee $20.00/couple
$10.00 additional son
Saturday, February 15, 2020
K thru 3rd 9:00 – 10:30 am
4th thru 6th 10:30 – Noon
at the Elementary School Gym.
Battle it out with your lil’ rambo in this all-new nerfpocalypse!
This event will feature nerf wars, nerf games, crafts, prizes & an ice cream sundae bar.
Bring your own nerf gun (bullet style – no ballistic rapid fire guns) bullets provided.
Protective goggles are required.
Registration ends Jan. 31, 2020.
Limited to 50 boys.