Make your life happening by enrolling to entertainment events in Winterset. Find a partner through a salsa night or take your partner to live in concerts by upcoming bands in your town. Get high while playing Beer Pong in a pub crawl or attending stand-up comedy events in Winterset. Shake your legs in the happy streets, zumba or dance workshops or go for a film screening in the nearby cafes or theaters.
Explore Entertainment Events in Winterset.
## Trending Events in Winterset - **Event Name**: Decades on the Orchard - **Description**: Decades on the Orchard, a one-night music festival celebrating the songs, sounds and nostalgia of generations, to Winterset Cidery on Saturday, October 17, 2026 from 5-11pm.Set among the orchard at Winterset Cidery, - **Venue**: Winterset Cidery - **Banner**: https://cdn2.allevents.in/thumbs/thumb6aa9fc1e5c180.jpg - **Event Name**: 2026 Madison County Covered Bridge Festival - **Description**: Please join us in Madison County, Iowa, for the 2026 Madison County Covered Bridge Festival! Saturday, October 10th, from 9:00 am to 7:00 pm, and Sunday, October 11th, from 9:00 am to 3:00 pm (parade starts at 3:00). Every second full weekend in October s - **Venue**: 73 E Jefferson St, Winterset, IA, United States, Iowa 50273 - **Banner**: https://cdn-az.allevents.in/events8/banners/6e965bc4713dacbc3eb292e35d161926cdd867304c4dc1063e5d3d4b63dedd89-rimg-w1200-h444-dc080808-gmir?v=1788427452 - **Event Name**: Fly Iowa Festival 2026 - **Description**: Join us for an unforgettable day of aviation, community, and celebration at the Fly Iowa Festival 2026! UPDATE: Come see the famous YL-37 Flying Memorial and take a ride in a PT-19!! More aircraft announcements to come! 📅 Saturday, September 19, 2026 - **Venue**: Winterset Municipal Airport - **Banner**: https://cdn-az.allevents.in/events7/banners/a2e8240cae6c722f64d1eaa576d5334c02112463ad5761cdf0cb507f266ba958-rimg-w1200-h1649-dcd8d8c8-gmir?v=1787167055 - **Event Name**: Free Pop-Up @ Winterset Cidery with Pure Barre WDM - **Description**: Join us for a special Pure Barre community pop-up at Winterset Cidery on Saturday, September 19 at 1pm! We’ll kick off the afternoon with a FREE outdoor Pure Barre class surrounded by the beautiful Iowa countryside. Members, friends, and first-timers are - **Venue**: Winterset Cidery - **Banner**: https://cdn-az.allevents.in/events10/banners/4dfa403217abf98a94bb6eb84fded17fa39d9abf401e9c50711bb170b31d374c-rimg-w1200-h676-dcb88868-gmir?v=1787470845 - **Event Name**: Pumpkin Palooza - **Description**: Our annual end of the season bash at Speckled Hen Farms! Join us to celebrate another season on the farm with Pumpkins and gourds for sale, fresh pressed apple cider, mini donuts, farm freah seasonal treats and the farm store loaded with funky fall merch - **Venue**: 1578 North River Trail, Winterset, IA - **Banner**: https://cdn-az.allevents.in/events2/banners/02f41389702de04b4a9d257368853f8c6ed186fc2393a67a42a6e02f6e1b7542-rimg-w1200-h1600-dc383838-gmir?v=1786941984 - **Event Name**: Madison County Fall Crawl - **Description**: The Madison County Fall Crawl is a small, local event near Winterset, IA that takes place on the last Sunday in September. Take a drive with friends around Madison County to see 15 small local businesses in their rural setting. There are a few stops alon - **Venue**: 1823 225th St, Winterset, IA - **Banner**: https://cdn-az.allevents.in/events9/banners/6d676bf5d0d6316d90226646c99340f6d6cc29402e9b1f0a21877792679c7624-rimg-w960-h350-dcf8f8f8-gmir?v=1787732881 - **Event Name**: Fall Into Fashion: Sip. See. Shop. - **Description**: Get ready for another exciting Runway on 2nd event... brought to you by the Winterset Retail District! 🍂 TICKETS NOW AVAILABLE 🍂 Fall Into Fashion: Sip. See. Shop. Saturday, September 19, 2026 VIP Early Access: 9:15 AM Doors Open: 9:30 AM Show: 10:00–1 - **Venue**: 231 N 2nd Ave, Winterset, IA, United States, Iowa 50273 - **Banner**: https://cdn-az.allevents.in/events5/banners/86a318c0c2129f6b8aac034e6324a333ed1ecf117952298e156ee23bbb76c020-rimg-w1200-h697-dcf8e8d8-gmir?v=1787219278 - **Event Name**: Sunday Funday at Winterset Cidery - **Description**: Sunday Funday is here! Join us for a beautiful August afternoon at Winterset Cidery! Gather your family and friends, bring a lawn chair or picnic blanket, and spend the day making memories at the orchard. Whether you’re sipping on a refreshing cider, en - **Venue**: 1638 Highway 169, Winterset, IA - **Banner**: https://cdn-az.allevents.in/events5/banners/d9ee5def48a7a27fba1cf9f69a2a01400b02cf373eedb6fc25cfa0ede714a5c8-rimg-w940-h788-dc282828-gmir?v=1787167073 - **Event Name**: Evening Under the Stars 2026 - **Description**: You're invited to an unforgettable Evening Under the Stars as the Madison County Foundation for Environmental Education hosts its annual Fundraising Dinner & Auction on Saturday, September 19, 2026. Join us for an evening of great food, local beverag - **Venue**: 2508 Pammel Park Trail, Winterset, IA, United States, Iowa 50273 - **Banner**: https://cdn-az.allevents.in/events1/banners/b46bffaf0f7e966ec66c04c2b6c2afd9e86baeefcadae28dd82743e85780db66-rimg-w525-h422-dc080808-gmir?v=1788590879 ## Browse Entertainment Events by Date - [Entertainment Events Today in Winterset](https://allevents.in/winterset/entertainment--today) - [Entertainment Events This Weekend in Winterset](https://allevents.in/winterset/entertainment--this-weekend) - [Entertainment Events in September in Winterset](https://allevents.in/winterset/entertainment--september) - [Entertainment Events in October in Winterset](https://allevents.in/winterset/entertainment--october) ## FAQs - **Q**: How can I find Entertainment events in Winterset? - **A:** You can discover upcoming Entertainment events in Winterset on AllEvents.in. Browse by date, venue, or price to find events that match your interests. - **Q**: How do I buy tickets for Entertainment events in Winterset? - **A:** You can buy tickets directly through AllEvents.in. Many events offer online booking with options for free, paid, and early-bird tickets. - **Q**: Are there any online Entertainment events available? - **A:** Yes, many Entertainment events are available online. You can filter for virtual events on AllEvents.in to attend from anywhere. - **Q**: How can I get notified about new Entertainment events in Winterset? - **A:** Follow the Entertainment category on AllEvents.in to get notified when new Entertainment events are listed in Winterset. ## Category Banner - **Banner Image**: https://cdn2.allevents.in/transup/58/5efbefdb8e438db5c829e697673309/Maskgroup-3-.webp ## Entertainment events from nearby cities - [Entertainment events in Saint Charles](https://allevents.in/saint-charles-ia/entertainment) - [Entertainment events in De Soto](https://allevents.in/de-soto-ia/entertainment) - [Entertainment events in Adel](https://allevents.in/adel-ia/entertainment)