This week in Madison County…

October Citizen of the Month: Natalie Montross
Presented by the Madison County Chamber of Commerce

Natalie Montross: A Legacy of Service, With an Eye on the Future
When Ben Garrison needs to connect someone with help in Madison County, he knows who to call.
“I lean on Natalie a lot for community resources, both local and on the state level,” he wrote in nominating Natalie Montross for the Madison County Chamber of Commerce’s Citizen of the Month. “If I am looking for resources to help someone, my first call is always Natalie.”
It’s a simple statement, but it speaks to the kind of trust that grows through years of showing up for others. After three decades with the Winterset Community School District and years of involvement with community organizations, Montross has built a deep understanding of the people, programs, and resources that help Madison County families.
For October, the Chamber is recognizing Montross for her years of service and her commitment to a community she has long called home.
A Community That Feels Like Home
Montross has lived in Madison County since she was two years old, with the exception of about ten years in Omaha, Nebraska, where she attended college and worked. After returning, she continued building her life and career here, spending the past 30 years with the Winterset Community School District.
What she appreciates most about Madison County is its rural beauty and family-friendly atmosphere. She describes it as a safe place to raise children, where people care about one another. Most importantly, she says, it is home.
That sense of belonging is reflected in how she talks about service. For Montross, community involvement isn’t simply about filling a volunteer position or adding another responsibility to the calendar. It’s about helping people feel supported, valued, and empowered—and making sure families have the resources they need.
Over the years, she has served on several community boards and participated in local programs. Her more recent involvement has included CRISP, the Opiate Task Force, Paw Pantry, and Madison County Partnership. These connections have given her opportunities to support local families and contribute to the well-being of the community she loves.
Garrison’s nomination reflects the reach of that work. He described Montross as someone with connections to nearly every kind of community resource, adding that people who have lived here for any length of time and needed help—or helped someone else—likely know who she is.
Learning What It Means to Serve
Montross credits several people with shaping the way she approaches community service. Her parents, June and Russell Williams, were important influences, as were Pat Sullivan, whom she worked alongside for 18 years, and Jim and Pat Nelson.
She describes them as examples of leadership, service, and encouragement. Through their example, she learned the importance of leading with heart, serving others, and helping people recognize their own potential.
Her faith is another central part of her motivation. Montross believes people are called to use the gifts and talents they have been given to serve and love others. That belief continues to guide her, giving her energy and purpose even when the work is challenging.
She also recognizes that service doesn’t look the same for everyone. Some people find joy in working directly with others; others may be better suited to organizing projects, sharing professional skills, or contributing financially to programs that make a difference.
Her advice is to find something that brings you joy and put your talents to use. Rather than feeling pressure to make a major commitment right away, she encourages people to start with something short-term and low-pressure until they find the right fit. And when volunteering becomes difficult, she suggests returning to the reason you started in the first place.
Making Room for the Next Generation
One of Montross’s most important concerns is what happens next. After years of community involvement, she understands that today’s volunteers and leaders won’t be able to carry every responsibility forever. As people begin stepping back from leadership roles, new people will need to be ready to step forward.
For Montross, that means making a deliberate effort to encourage young people to become involved in their communities. If Madison County wants to continue making a difference for youth and families, she believes it must invest in the next generation of volunteers and leaders.
That investment starts with helping young people discover their interests, recognize the gifts they have to offer, and understand that even a small commitment can make a lasting difference. It’s a reminder that community service isn’t reserved for people with decades of experience. There’s room for people at every stage of life to contribute, learn, and find a way to make their community stronger.
A Community Where People Belong
When asked what she hopes to accomplish through her service, Montross returns to a straightforward goal: she wants to leave Madison County better than she found it.
She hopes families feel empowered, supported, and fortunate to live in a place where they are seen, valued, and genuinely cared for. To her, a strong community is one where people feel they belong, families can access the support they need, and everyone has the opportunity to thrive.
It’s also a community where service continues beyond any one person’s contributions. By encouraging others to get involved—especially those who will carry the work forward—Montross hopes to help build a lasting legacy of care for Madison County.

A special note from Natalie to her husband Steve: “I am very blessed to have a husband who will partner with me whenever I ask.” And if you’ve met Steve, you know he has a heart for service as well. Thank you both for all that you do for your community!
The Madison County Chamber of Commerce is proud to recognize Natalie Montross as its October Citizen of the Month. Her years of service are a reminder that strengthening a community takes people who care enough to get involved, build connections, and help others find their footing.
And as Montross herself reminds us, everyone has something valuable to offer.
Today/Tonight
Optimist Club FUN NIGHT
Thursday • October 29 • 5:30-7:30 pm
Winterset Middle School

Optimist Fun Night is back! ![]()
The Optimist Club of Winterset invites all students in TK–3rd grade to their annual Fun Night celebration! Get ready for an evening filled with games, snacks, prizes, and plenty of fun! ![]()
Winterset Middle School
Thursday, October 29
5:30 – 7:30 p.m.
Sponsored and supervised by the Optimist Club of Winterset
Parents are welcome, but not required to attend
No costumes, please
Hot dogs and cookies available!
Ghostbusters
Thursday • October 29 • 7:00 pm
Throwback Thursday at The Iowa Theater
1/2 off popcorn on Throwback Thursday!
After the members of a team of scientists (Harold Ramis, Dan Aykroyd, Bill Murray) lose their cushy positions at a university in New York City, they decide to become “ghostbusters” to wage a high-tech battle with the supernatural for money. They stumble upon a gateway to another dimension, a doorway that will release evil upon the city. The Ghostbusters must now save New York from complete destruction. 1984, Rated PG, 1hr 47min
Thank you to our sponsors!
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This Week!
Halloween around Madison County!

Daily Through November 1st
- Fall activities at Howell’s Green House & Pumpkin Patch
Saturday October 24th
- 10am-1pm – Trick or Treat at Winterset HyVee
- 5-8pm – Haunted Harvest Festival at Madison County Conservation Center
- 6-8pm – Halloween Hullabaloo Winterset Junior High Dance
- 6-9pm – Costume Party & Live Music at Big Rack Brew Haus
Friday October 30th
- 330-5pm – Fall Event at Summerset Realty
- 330-5pm – Trick or Treat on the Winterset Square
- 5-7pm – Beggar’s Night, City of Winterset
Saturday October 31st
- 12-5pm – The Orchard Holiday Market at Winterset Cidery
- 5-6pm – Not So Scary Halloween at Earlham Community Center
- 5-6pm – Trick or Treat, Earlham Business District
- 5-7pm – Trunk or Treat on Main Street, Saint Charles
- 5-7pm – Beggars Night, City of Saint Charles
- 5-8pm – Costume Party and Live Music at Winterset Cidery
- 6-8pm – Beggars Night, City of Earlham
Sunday November 1st
- 12-5pm – The Orchard Holiday Market at Winterset Cidery
Senior Speaker Series: Iowa Unique Eats and Eateries w. Book Signing
Friday • October 30 • 10:00 am
Bricker Price Block, Earlham

Trick or Treat Around the Square
Friday • October 30 • 3:30-5:00 pm
Winterset Town Square

🎃 Downtown Trick-or-Treating is Coming! 👻
In partnership with the City of Winterset, we’re excited to welcome families downtown for an afternoon of Halloween fun!
Friday, October 30th – 3:30–5:00 PM
Downtown Merchants: If you would like to participate, please plan to set up outside your front door to hand out treats during the event.
REMINDER: We will not be placing participation decals in business windows. Setting up outside will make it easy for families to see which businesses are participating as they make their way around downtown. If you are NOT located on the downtown square but would like to participate, reach out to the chamber and we will help find an available location for you.
We’re looking forward to a fun afternoon of costumes, treats, and community in Downtown Winterset!
Fall Event at Summerset Realty
Friday • October 30 • 3:30-5:00 pm
Summerset Realty, Winterset

Movie at The Iowa Theater: Death on the Brandywine
- Friday, October 30 – 7:00PM
- Saturday, October 31 – 7:00PM
- Sunday, November 1 – 2:00PM
After a prominent politician is declared dead by suicide, his daughter enlists her partner to investigate. Their search unravels a lethal tangle of family secrets and political betrayal that someone is desperate to hide.
Co-starring Satomi Hofmann!
2026 Not Rated, 1hr, 38min
It’s a GREAT day to be a Citizen—
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This Weekend!
Orchard Holiday Market
Saturday-Sunday • October 31-November 1 • 12:00-5:00 pm
Winterset Cidery

JOIN US FOR AN ORCHARD HOLIDAY MARKET!
We’re bringing a little holiday magic to the orchard! Winterset Cidery is partnering with Xperience Candle Bar to host a unique and festive Holiday Market featuring local vendors, shopping, and a fun weekend at the Cidery!
14 Saturday, October 31 & Sunday, November 1 12-5 PM both days, at Winterset Cidery.
Shop local vendors and find something special for everyone on your holiday list!
SATURDAY NIGHT | 5-8 PM
Stick around after the market for live music by FunHouse and enjoy a Saturday evening at the Cidery!
ARE YOU A VENDOR?
We’d love to have you join us! Vendor applications are now open. Apply using the link below: https://docs.google.com/../1FAlpQLSf35iMjPkG../viewform..
And stay tuned… we’ll be announcing our AMAZING vendor lineup soon!
Come shop local, sip some cider, and kick off the holiday season with us!
FunHouse Live & Halloween Costume Party
Saturday • October 31 • 5:00-9:00 pm
Winterset Cidery


HALLOWEEN FUN BY THE ORCHARD!
Join us on Halloween evening for a whole lot of FUN at Winterset Cidery! Enjoy live music by FunHouse from 5-8pm, a costume contest, fire pits, s’mores, and plenty of Halloween fun for the whole family!
Costume Contest Schedule:
- Registration: 5-7pm
- Costume voting: 5-7:30pm
- Voting closes: 7:30pm
- Winners announced: 8pm
Grab your costumes, bring the family, and come make some Halloween memories with us! We can’t wait to see you there!
Chris Carlisle at Big Rack
Saturday • October 31 • 6:00-9:00 pm
Big Rack Brew Haus

Come on out to Big Rack for some fantastic live music by Chris
Carlisle, great food by White Smoke BBQ, and of course, all of your
favorite Big Rack beer on tap and other tasty beverages!
$5 cover charge for the music, and cash or Venmo for food.
See you there!
Link to Facebook event: https://www.facebook.com/events/1584121250078509/
Christmas 4 Kids & Operation Santa Claus
Sign up by October 31!
by Matura and CRISP


Bomgaars Ladies Night
Sunday • November 1 • 5:00-8:00 pm
Winterset Bomgaars Store
Bomgaars is once again bringing its annual Ladies Night event to the community, combining an evening of fall shopping, festive fun and giving back to local organizations.
On Sunday, November 1, 2026, from 5–8 p.m., Bomgaars customers at all locations will have the opportunity to enjoy special savings, giveaways and an evening dedicated to supporting the communities Bomgaars is proud to serve.
As part of Ladies Night, 5% of the evening’s sales will be donated to a local charitable organization in each Bomgaars community. This year, Madison County Health Care System has been selected as the recipient for the Winterset community.
The donation will be presented to Madison County Health Care System in December 2026, with the amount based on sales from the local Bomgaars store during Ladies Night.
“We believe being a good neighbor means more than simply having a store in a community,” said Torrey Wingert, CEO of Bomgaars. “Our communities support us throughout the year, and Ladies Night gives us an opportunity to give something back to organizations that are making a difference right here at home.”
For more than eight years, Bomgaars has used Ladies Night as an opportunity to support organizations in the communities where its stores are located. What began as a way to support local cancer centers, hospitals and women’s organizations has grown into an annual community-giving event across Bomgaars’ store markets.
Madison County Health Care System is grateful to be part of this year’s event.
Customers are invited to join Bomgaars for an evening of shopping, savings and community support. Come enjoy a fun evening at Bomgaars while helping support an organization that is making a difference in the Winterset community.
Website: https://www.bomgaars.com/ladies-night
FB Event Page: https://www.facebook.com/share/14p6yKiDmFn/
Bloody Mary Sunday
Sunday • November 1 • 11:00 am-5:00 pm
Big Rack Brew Haus

Set your clocks back an hour and join us for November Bloody Mary Sunday Funday at Big Rack and Day of the Dead – loaded Bloody Mary drinks, cold Big Rack Beer on tap, and White Smoke BBQ will be here serving up some great food!
We look forward to seeing you there!
Link to Facebook event: https://www.facebook.com/events/1670914694745513/
November Highlights at Bit of a Stretch Wellness
Bit of a Stretch Wellness, Saint Charles

Make a little room for yourself this November. Join us at Bit of a Stretch Wellness in St. Charles for movement, rest, and connection. This month’s highlights include:
A Cozy Author Evening: Meet local author and studio owner Nicole Nichols at Tiger Lily Café on November 4, 5:30-6:30 PM. Pick up a signed book and settle in for a little conversation.
Sunday Restore with Haley: Slow down with restorative yoga on November 1 and 8, 6-7 PM.
Tuesday Evening Flow with Haley: Move, breathe, and make time for yourself on November 3, 10, and 17, 5:30-6:15 PM.
The Gathering, Ladies Night: Join us November 10, 6:30-8 PM, for an evening of connection and room to simply be yourself.
Come for a class, a conversation, or a much-needed pause. We’d love to welcome you.
Details and reservations: https://www.bitofastretchwellness.com
Thank you to our sponsors!
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Next Week
Holiday Market on the Farm
Saturday • November 7 • 10:00 am-4:00 pm
Speckled Hen Farms

Join us for our annual Holiday Market On The Farm event! Your 1st stop for getting you in the Holiday spirit! Enjoy a 1 if a kind ” open air ” style market featuring unique, local vendors and small businesses spread out between the Farm store/ patio and Lone Oaks Barn! Food, music, wine, shopping, and even a visit from Santa and Mrs. Claus! This is one of those events you don’t want to miss! Free fun for all!
A Tonight Show Christmas
Saturday • November 7 • 12:00 pm
First Christian Church, Winterset




It’s a blast from the past – 1960’s style. Written and directed by Steve Hickle, this artistic presentation of the Tonight Show has a star-studded lineup! Join us for conversations with and performances by Judy Garland and Ethel Merman. There will also be appearances by Winterset’s own Belly Up dance troupe. Don’t miss this chance to relax and reminisce.
This production will be held on the Fellowship Hall Stage of First Christian Church. It will kick off with a luncheon at 12 noon, with the show to follow. Reservations are encouraged.
Preshia Paulding (Judy Garland) has been an entertainment fixture in the Des Moines metro for years. She has played Judy Garland in Judy’s Scary Little Christmas and in Beyond The Rainbow andreceived a Dionysos Award at the Des Moines Community Theater for Outstanding Performance. Her extensive résumé includes theatre, radio voiceovers, jingles, the Kris Kristofferson mini-series, Amerika, and several films.
Jennifer Phelps (Ethel Merman) is an Iowa native, born and raised in the Des Moines area. She has made appearances on stage at the Des Moines Playhouse in several shows, notably as Mrs. Brill in Mary Poppins and as Mother Superior in Sister Act. She has also performed the National Anthem at various venues across Iowa, including the Iowa Cubs, Iowa Barnstormers, and Knoxville Raceway.
Under the direction of Connie Lawrance, Belly Up Dance Troupe has been dancing together since 2022. Their style is inspired by many cultures and traditions, including classic Middle Eastern movements, with a focus on group interaction. In addition to performing locally, they host a yearly workshop in Winterset, Iowa, bringing in professional instructors for a weekend of classes and performances. It is a source of positive support for the dance community and financial support for local businesses.
Steve Hickle (writer/director/host) has been active in community theatre for over 25 years. His most recent role was Jud in Oklahoma at Winterset Stage. Other roles include Mr. Greenway in Elf The Musical at Pella’s Union Street Players and Fiddler On the Roof at the Des Moines Playhouse.
When: 12 noon, Saturday, November 7.
Where: First Christian Church, 103 W. Green St., Winterset, IA.
Cost: Free Will Offering (cash or check made out to First Christian Church)
To make reservations: Leave a message at First Christian Church (fccwinterset@gmail.com / 515-462-1276) with your name, phone number, and number of seats requested.
Beginner Sourdough Workshop
Sunday • November 8 • 1:00-3:00 pm
Winterset Cidery

Ready to start your sourdough journey? Join us at Winterset Cidery with Counter Culture Sourdough Co for a hands-on Beginner Sourdough Workshop!
Whether you’re brand new to sourdough or just looking to learn something new, this is the perfect opportunity to roll up your sleeves, learn the basics, and have some fun!
A ticket is required to participate in the workshop! Be sure to grab your ticket in advance to reserve your spot.
Gather your friends, come learn something new, and spend a fun afternoon by the orchard!
Coming Soon
Women’s Giving Circle Holiday Potluck Party
Tuesday • November 10 • 6:00-7:00 pm
Union State Bank Community Room, Winterset

Madison County Women’s Giving Circle 2026 4th quarter Holiday potluck/party
The Madison County Women’s Giving Circle 4th quarter Holiday Potluck/party will be November 10th, 6:00 pm to 7:00 pm at the Union State Bank Community Room, 611 West Hwy 92, Winterset. You may come at 5:30 pm to 7:00 pm if you wish to socialize more. There will not be a “business” meeting. Please bring your check for your annual donation to our Community Foundation Account. You are also encouraged to bring a snack, side, dessert, etc. to share at the potluck. Feel free to invite potential members to join us to learn more about the organization.
Little Women: The Broadway Musical
by the WHS Theatre Department!
Sunday • November 13 • 7:00 pm
Monday • November 14 • 2:00 pm & 7:00 pm
Tuesday • November 15 • 2:00 pm
at The Warehouse on 2nd

Thank you to our sponsors!
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Cocoa Crawl
Saturday • November 14 • 10:00 am-3:00 pm
Winterset Town Square

2026 COCOA CRAWL IN HISTORIC WINTERSET!
Calling all cocoa lovers, holiday shoppers, and anyone who believes chocolate makes everything better!
Grab your friends, bring the family, and join us for a sweet day of sipping, shopping, and exploring beautiful Historic Downtown Winterset, lowa!
Stroll around our charming town square as local businesses come together to celebrate all things COCOA!
Here’s what’s brewing:
- Delicious cocoa-inspired treats, drinks, and sweet surprises at participating businesses!
- Fun holiday activities to get you in the festive spirit!
- Special sales, unique gifts, and holiday shopping throughout downtown!
- A chance to support the amazing small businesses that make Winterset so special!
How do you join the fun?
Simply look for the official Cocoa Crawl poster displayed at participating businesses and stop in to see what sweet surprises await!
Whether you’re a hot cocoa fanatic, a chocolate lover, or just looking for a fun fall outing with a little holiday magic, there’s something for everyone!
Sip a little. Shop a little. Support local A LOT!
Mark your calendars, tag your cocoa-loving crew, and come experience the sweetness of small-town Winterset!
*Please note: Offerings vary by business, and not all participating locations will serve hot cocoa.*
Holiday Open House
Saturday • November 14 • 10:00 am-3:00 pm
Evergreen & Lily Floral

Join us at Evergreen & Lily Floral for a little holiday magic! ![]()
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Whether you’re looking for the perfect Christmas gifts, holiday inspiration, or just an excuse to get out and enjoy the season, we’d love to see you!
Here’s what you can look forward to:
Holiday shopping
A cozy cocoa crawl
Festive photo opportunities
Door prizes and holiday fun
Saturday, November 14, 2026
10:00 AM – 3:00 PM
Evergreen & Lily Floral
419 S. John Wayne Dr., Winterset, IA
Grab your friends, bring your holiday spirit, and come spend the day with us!
Holiday Farm Shop
Saturday • November 14 • 9:00 am-4:00 pm
PepperHarrow

The farm is trading lavender rows for evergreens. Join us Saturday, November 14 from 9AM to 4PM for our Holiday Farm Shop.The event barn will be full of fresh greenery, farm-made gifts, and holiday cheer.
Here’s what you’ll find:
Fresh evergreen wreaths and our signature evergreen wreaths, decked out with flowers we grew and dried on the farm this summer.
Holiday greenery baskets, ready to set by your front door.
Our handmade lavender line, made in small batches with lavender from our 18,000+ plants: soaps, salves, candles, essential oils, and lavender tea.
Our hand-poured soy candles, made in small batches right here on the farm. They make an easy gift, or a cozy treat for yourself.
PepperHarrow flower seeds for the gardener on your list, and a little something to look forward to in spring.
Gift-ready bundles and stocking stuffers.
Bring your holiday list, grab a friend, and make a day of it in Madison County. We’re 35 minutes from Des Moines, and you can see the covered bridges on the way. Greenery and wreaths are first come, first served, and they go fast, so come early for the best selection.
Can’t make it? You can shop lavender products and seeds anytime at pepperharrowfarm.com.
We can’t wait to celebrate the season with you!
— Jenn and Adam
LIVE WILD: Traditional Basket Weaving
Tuesday • November 17 • 6:00-7:00 pm
Madison County Conservation Center

Join us for a hands-on Flat Reed Basket Weaving Workshop on November 17 at 6 p.m.! Participants will have the opportunity to learn and practice traditional Cherokee-style round reed basket weaving while creating a basket of their own. This workshop offers a chance to explore a traditional art form and enjoy an evening of creativity.
Open to adults and children ages 8 and older, this program is geared primarily toward adults. The workshop fee is $15 per participant. Preregistration is required.
Santa at Stepping Stones!
Saturday • December 5 • 1:00-3:00 pm
Stepping Stones Child Care Center


Chamber Members: We would love to include your upcoming events in the weekly snapshot, Chamber Chat and The Citizen.
Chamber Chat is great for business-to-business communication, while The Citizen is the perfect way to reach the wider community!
To ensure you get included, please email your event information to communications@madisoncounty.com by the Friday before publication.















