Coming Soon:

Where Madison County Creates

Register for Where Madison County Creates

Registration is not required, but the first 100 registrants receive a free gift bag with coupons to area retailers, make-and-take kits to complete at participating locations, and more! Pick yours up at the Chamber of Commerce office, starting Saturday morning at 10 am.

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Madison County Covered Bridge Festival

October 8-9, 2016

Click here for Covered Bridge Festival Information, Schedule & Details!


Annual Visitor Events & Festivals

Winterset Chocolate Walk, February

Held on the Saturday before Valentine’s Day, the Winterset Merchants Group invites you to come in from the cold and enjoy decadent chocolate creations while you shop around the square for your sweetie! Take a look at what they have to offer: gifts, cards, chocolates and other gourmet foods, arts, crafts, jewelry, accessories, kitchen gadgets and home decor, and many one-of-a-kind treasures found only in Madison County. Participating merchants will offer bite-sized samples, Valentines Day specials, and “sweet” deals!

Winterset Wine Walk, May

The Winterset Wine Walk is typically held on the Saturday evening of Mother’s Day weekend, making it a great opportunity for a girls’ night out, a date with Mom, or just a fun outing with family and friends. From 4:00 to 7:00 pm all around the Winterset square, merchants will sample wines from our local area wineries, along with serving tasty treats and offering special deals on goods and services. Participants receive a commemorative wine glass and a $5 coupon towards the purchase of a bottle of wine from a featured winery (to be used that night only). Tickets go on sale approximately one month before the event and are available at the Chamber of Commerce office, 73 Jefferson Street in Winterset.

John Wayne Birthday Celebration, May

In celebration of the May 26 birthday of John Wayne, Winterset hosts an action-packed festival on Memorial Day Weekend. It’s a event befitting a true American icon! Scheduled activities typically include a 5K run/walk, pancake breakfast, benefit dinner and live auction with high profile entertainment, and more. Some events are different each year, such 2016’s all-horse parade, country barn dance, and equestrian drill team presentations. Many John Wayne fans make an annual pilgrimage to Winterset to attend. We hope you’ll check it out!

Winterset Ladies Night Out, June

Winterset Ladies Night Out is typically held on the second Friday of June, from 6:00-9:00pm. Come to our historic uptown business district and enjoy shopping, wine tasting, food samples, fashion and accessories, photos, girl time, and more. The first 200 ladies to pre-register for the event will receive a FREE goody bag filled with samples, gift items, and coupons. Grab your girlfriends, your mothers or daughters, and enjoy a Madison County evening designed just for you!

Krazy Days Sidewalk Sales, July

Held the last weekend in July, businesses all around the square will host sidewalk sales with crazy discounts. A great time to come and bargain hunt!

Where Madison County Creates, September

Part of the Southwest Iowa Art Tour, “Where Madison County Creates” is a self-paced tour of local art studios and creative spaces where you can meet local artists, watch live demonstrations, learn some new techniques, and get inspired.

Madison County Covered Bridge Festival, October

The annual Covered Bridge Festival, held on the second weekend in October, is a time-honored tradition of celebrating our local heritage with arts and crafts, vendors and demonstrations, farmers market booths, wineries, quilt and car shows, family entertainment, and more. We’re currently accepting applications for vendor space. We encourage you to apply for booth space, and look forward to hosting you at the next Covered Bridge Festival!

See more…

Small Business Saturday, November

Come to Winterset and enjoy a small-town shopping experience like none other on Small Business Saturday, always the Saturday after Thanksgiving. Begin your day with a pancake breakfast, shop for steals and deals in our quaint, unique shops, enjoy a horse and carriage ride, and get in the spirit of the season. Downtown businesses are offering special drawings and discount rewards for supporting small business on Small Business Saturday. Special “Small Business Saturday” tote bags are available with qualifying purchases. Join the movement and Shop Small!

Festival of Lights, November

The Festival of Lights event in Winterset is the official kickoff to the holiday season, and we invite YOU to attend! Activities happen around the courthouse square on the last Friday of November and feature FREE activities for young and old alike. Activity highlights include live music, a visit from Santa Claus, hot food and drinks, holiday shopping specials with local businesses, a lighted parade, gingerbread house contest, strolling carolers, festive luminaries, and more. Come to Winterset for an official holiday season kickoff!