Indianola and Winterset Winery Loop: a gentle afternoon drive from Osceola

Sometimes the best afternoons are slow on purpose. You check into The Jeffreys, drop your bag, and decide a short drive and a couple of tastings sounds just right. This loop keeps it simple… sample two or three wineries, light snacks, and a scenic route back before dark. All that's left is making s straight forward plan.

Stop 1: Summerset Winery, Indianola

Roll north to Summerset’s hillside vines and easy parking. Book a tasting, enjoy the patio, and let the views do their thing. It’s relaxed, friendly, and close enough that you’re never racing the clock. If you’re here on a weekend, check for tours or live music.

Stop 2: Covered Bridges Winery, Winterset

Head west for small town charm and a tidy tasting room just off Highway 169. Flights run smooth, the staff knows their grapes, and fall sunsets over the hills are worth the drive alone. Watch their calendar for seasonal events and “Music at the Winery” nights if you want to linger.
Plan it: coveredbridgeswinery.com

Optional add: Madison County Winery, St. Charles

If you’ve got another hour, tuck in a third stop at this countryside tasting room. Patio seating, vineyard views, and an easygoing lineup make it a mellow finish before you point the car south.
Plan it: madisoncountywinery.com
Note: Some venues host private events or shift hours seasonally. Peek at websites before you roll so the timing stays smooth.

Pacing that feels good and a picnic add-on

• Start after a late breakfast.
• One flight per stop is plenty if you want the drive to stay relaxed.
• Share tastings, sip water, and plan a snack at each winery.
• Head back before dusk so the last miles feel calm and easy.

Pack a light picnic for the car or a table outside: cheese, crackers, apples, nuts, and plenty of water. Some tasting rooms offer snacks, but a small cooler keeps the day flexible.

Responsible tasting and simple safety

Short drive, calm tastings, pretty views, and you’re back in Osceola before the streetlights flip on. That’s a good afternoon!

Keep it responsible for the best, safest time. Choose a designated driver or share flights and keep pours light. Drink water, eat something at each stop, and give yourself breaks. You’ll enjoy the day more when the pace stays easy.

If you’re building a fun or quiet weekend, start here, check out the main the main page on our website and scroll down for our blog including all you need to know about Osceola's thriving community, parks and recreation, access to supplies and local businesses.