Madison County Fall Crawl

10/09/2026

You’ll want to bring cash for festival admission — it’s $3 per person (kids 11 & under are free).

Most festival vendors and merchants accept cards, so you don’t need to carry cash for everything!

📅 October 10–11
📍 Madison County, Iowa

Save this reminder and share it with your festival crew! 🍂

10/08/2026

This weekend

10/03/2026

2027 Fall Crawl Passport Winner Announcement!

Our annual passport draw is totally random and based upon your passport stamps! If you stopped at each location, it means you had more chances to win! We’re always amazed at how many people who made it to all 15 stops in one day! Ya’ll are dedicated and we love that!

Drumroll for the winners please!

Pammel Park Coffee Co - Lisa H.
Tshirt, Travel Mug & bag of Coffee

Cedar Shake Farm - Callie D.
Veggie Box & Fall Crawl Stocking Cap

Bigelow Family Farms - Jan S.
Mahogany stool/bench, 4lbs of ground & 2 pkg of beef sticks

PepperHarrow - Elizabeth (No last name listed)
Lavender Collection Box

Judge Lewis House - Amarna K.
Goodie Basket, Veggies, Walley Book & tshirt

The Drift - Caasi H.
$25 Gift Card

Covered Bridges Winery - Crystal M.
$25 Gift Card

Winterset Cidery - Emily R
Goodie Bag w/ mug, hat, drink pogs & more.

Speckled Hen Farms - Isaac S.
Farm Box

Lone Oaks Farm - Nancy C.
Homemade Spoon Rest & Fall Crawl stocking cap

Iris Aisle - Candace E.
Iris Aisle tshirt & Fall Crawl stocking cap

Simple Life Farms - Katie W.
Goat Milk Lotion Kit

Big Rack Brewery - Andrea H.
$25 Gift Card

Kaysen Family Farms - Topper G.
$25 Gift Card

Madison County Winery - Haley C.
$25 Gift Card

Secret Passport Phrase Winner - Jason M. : Fall Crawl Tshirt, Stocking cap & mug

The Secret Passport Phrase this year was : JUMP INTO FALL

We will be calling/texting winners by Sunday to determine best time to pickup/snag your item. Feel free to ping us on Insta or Facebook msgr if you see your name as a winner! We can get you all the deets! Those of you who won a gift card will pickup at the Winery or Brewery you won at. So swing on down for another sip and enjoy another round of what Madison County has to offer!

09/30/2026

Well friends, as your event organizers; we, Kelli & Clinton Eshelman just wanted to say thank you to everyone, from the vendors and stops to the attendees, family and friends for helping us with make the 6th Annual Madison County Fall Crawl event a success!

The soggy & muddy weather may have kept some away; but we still had parking lots & gravel roads lined with cars & trucks coming to crawl their way through Madison County! A big shoutout to thewanderingmidwesterner for her awesome social media work, posts and giveaways! Thank you!

We’re always looking for ways to improve the fall crawl, so let’s hear it friends! Tell us the good, the bad & the things you’d like to see more… or less of. This will always be a one-day event as that adds to the excitement of the passports and the fun rush of the day! Gives everyone a reason to come back next year!

We are already looking at some new things, but we want to keep that under wraps until we are in 2027! Put Sunday, Sept 26th, 2027 on your calendar for next year’s event!

We will be doing the passport drawings either tonight or tomorrow, depending on when we can get all the passports in. We’ll make a post and text/call all the winners directly!

Thanks friends!

09/29/2026

09/28/2026

🍂 THANK YOU for an incredible 2026 Madison County Fall Crawl! 🍂

What a day!

Thank you to everyone who came out, traveled the roads, visited our 15 stops, shopped with local vendors, enjoyed the food and drinks, listened to live music, explored the farms, and supported so many small businesses throughout Madison County.

A huge thank you to all of our host locations, vendors, musicians, food trucks, volunteers and everyone behind the scenes who helped make today possible. Events like this take a lot of coordination, and we truly appreciate everyone who played a part.

We’re also proud to share that 25% of all Fall Crawl vendor fees were donated to The Iowa Theater in Winterset. We love being able to use this event not only to support local businesses, but also to give back to our community.

And most of all, thank you to everyone who showed up and made the day so much fun. Seeing the roads full, the stops busy and people enjoying Madison County is exactly what Fall Crawl is all about.

🎟️ Passport prize winners will be announced over the next few days! Once winners are selected, we’ll work with you to arrange pickup or drop-off, or in some cases your prize will be available to pick up directly from the local business that donated it.

We hope you found a new favorite place, met some great people, ate something delicious and made a few memories along the way.

Thank you for making the 2026 Madison County Fall Crawl one to remember! 🍁❤️

See you next year!

09/27/2026

☀️🍂 NO RAIN — and the sun is coming out!

The Madison County Fall Crawl is underway, and the fun is just beginning!

Grab your passport, hit the road and start exploring all 15 stops across Madison County. There’s still plenty of time for local food, shopping, farms, wineries, live music, activities and more.

The weather is clearing up, so come on out and enjoy Fall Crawl Sunday with us!

🚗 Pick a stop and start anywhere
📍 Passports are available at all 15 locations … guess the secret saying to win some Fall Crawl SWAG!
🍂 No set route — make the day your own

Come see us — we’re just getting started! ☀️🍁

09/27/2026

🍂 ONE MORE SLEEP until the Madison County Fall Crawl! 🍂

Tomorrow is the big day — Sunday, September 27!

A little rain and wet weather won’t stop the fun, but it does mean you’ll want to come prepared.

🥾 Bring your boots
🌧️ Plan for wet, soggy grass
🛞 Expect some mud and wet gravel roads
👟 And maybe leave the white shoes at home!
🚙 Drive slow and watch for children, cats n dogs!

Some of our stops are farms and rural properties, so conditions may be a little messy in places. Dress for the weather, take your time on the roads, and come ready for a great day exploring Madison County. Avoid driving on your stop’s lawns if possible, it’s gonna be soft in places.

Don’t forget your passport stamps make a secret phrase. First one to send us the secret phrase on Facebook or Instagram wins some Fall Crawl Swag!

15 stops. Local food. Shopping. Farms. Live music. Activities. And plenty of Fall Crawl fun.

Get some sleep tonight — tomorrow we CRAWL! 🍁

09/26/2026

🍂🗺️ Your 2026 Madison County Fall Crawl Google Map is HERE!

Fall Crawl is TOMORROW — Sunday, September 27!

With 15 stops spread throughout Madison County, this Google Map will make it easy to plan your route, find each location and keep your Fall Crawl adventure moving all day long.

📍 Save the map before you head out:
https://maps.app.goo.gl/HnZceqrShintp5Lu7?g_st=i

Passports will also be available at all 15 Fall Crawl stops. Each passport includes a map along with direction information to help you navigate from stop to stop throughout the day.

Use the Google Map and your passport to:
🚗 Navigate between all 15 Fall Crawl stops
🍎 Plan your route for the day
🛍️ Find farms, wineries, food, vendors and shopping
🎶 Track down live music and activities
🍂 Explore Madison County along the way

There’s no required starting point and no set route — build your own adventure and visit as many stops as you can!

Grab your passport, save the map and get ready for the 2026 Madison County Fall Crawl! 🍁

09/26/2026

Eddie and Frankie would like to issue a PSA for tomorrow. We've had a ridiculous amount of rain for September. The ground is definitely saturated and very very squishy.

We recommend wearing appropriate footwear for crawling. I (Kelli) will personally be wearing either no shoes or boots. If you really love those Betsey Johnsons, leave them in the closet unless you appreciate a rustic, muddy look.

On that note, the gravel roads will be exceptionally wet as well. Please please please use caution while driving, the edge of the gravel can suck your vehicle right into the ditch if you're not careful.

As always, be courteous to your other crawlers and have fun.