Special Events

One of our most popular events! Sample locally-made wine and enjoy shopping specials, prizes and more at participating businesses around Winterset’s town square. Participants may purchase a commemorative wine glass at the Chamber of Commerce. Click "View More" to purchase tickets.

The John Wayne Birthplace & Museum has announced that legendary western performer Red Steagall will headline this year's John Wayne Birthday Celebration May 25 & 26. In his 45-year entertainment career, Steagall has enjoyed tremendous success as a hit-making singer and songwriter. He also hosts the award-winning RFD-TV show, "Somewhere West of Wall Street," and "Cowboy Corner," an hour-long syndicated radio program which airs on 170 stations in 43 states.
Born and raised in the Panhandle Plains of Texas, Steagall champions the rugged spirit and traditions of his forebears, the same spirit exemplified by John Wayne throughout his entire motion picture career. "If John Wayne had been a western singer, he'd have been Red Steagall," says Birthplace director Brian Downes.
The weekend kicks off with a screening of "Red River"(1948) on May 25 at Winterset's historic Iowa Theater. Starring John Wayne, Montgomery Clift and Walter Brennan, the classic western is a hard-hitting epic that captures the treacherous dangers of driving cattle up the Chisholm Trail. The screening will be introduced with stories and songs by Red Steagall. (The following night, May 26th, will feature Wayne in 1971's "Big Jake.")
Returning Celebration favorites on Saturday, May 26, will be Breakfast at the Firehouse and the Birthday Celebration's 5K Run/Walk, followed by an all-horse parade through picturesque Winterset. Fast becoming one of the premiere equestrian events in the Middle West, this cavalcade will include saddle and draft horses, mules, and all manner of wagons, carriages and coaches.
Wrapping up the celebration will be a Benefit Dinner featuring a musical performance by Red Steagall and an auction of John Wayne collectibles and memorabilia. Past auctions have featured vintage movie posters, original fine art and prints, rare autographs and commemorative firearms.
For further information and reservations visit: www.johnwaynebirthplace.museum or call 515-462-1044.

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events will be free to attend, and are sponsored by the Madison County Chamber of Commerce, Winterset Parks & Recreation Department, and Fareway Grocery Store. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars! June’s event features live music from Hot Tamale & the Red Hots.

A special weekend of classes, workshops, demos, entertainment, pampering, dining, shopping and much more! More information coming soon.

Featuring a parade, pedal tractor pull, RC car demo, food and craft vendors, and of course, a skillet throw. Click to see the full lineup as it develops.

Celebrate Independence Day in Earlham! Take part in a street dance, a parade, a pancake breakfast, tons of contest (including watermelon-eating and bubble gum blowing!), and fireworks, to name just a few. More details coming soon.

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events will be free to attend, and are sponsored by the Madison County Chamber of Commerce, Winterset Parks & Recreation Department, and Fareway Grocery Store. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars! July's event is sponsored by Lowe Chiropractic Clinic and features music by Matt Woods.

The Old Settlers event celebrates family fun and community involvement. St. Charles, Iowa is proud of its heritage and traditions. Many Old Settlers worked hard to build this little community! Lots of family entertainment all weekend long, from Cow Pie Bingo to entertainment on the new Community Stage.

Bring the whole family for events and activities, livestock and pet shows, grandstand events, contests, carnival rides and games, food and much more!

“First Fridays" Concert Series will be held in the north shelter area at Winterset City Park on the first Friday evening in the months of June, July, and August. These events will be free to attend, and are sponsored by the Madison County Chamber of Commerce, Winterset Parks & Recreation Department, and Fareway Grocery Store. Hot food will be available for sale, as well as beer, wine coolers, and bottled water. Food and beverages will be available for purchase beginning at 6:00 pm, and live music begins at 7:00 pm. Bring your lawn chairs and blankets, relax on the gently sloping hillside, and enjoy summer under the stars! August's event is sponsored by H&R Block and features live music by Gina Gedler and James Paulson.

Two days of music curated for all who love both music and the great outdoors. This annual festival features a blend of live music, camping, art, craft and food vendors, family activities and more. Held at the Avenue of the Saints Amphitheater in St. Charles.

Local artists team up to bring you live demonstrations and original artwork of all kinds, all around the community!

We invite you to visit the 2017 Madison County Covered Bridge Festival on October 14th & 15th to experience the world famous covered bridges, crafts and old-time demonstrations, annual quilt and car shows, cowboys from the wild west, continuous entertainment, family fun — and the many people and places that make it a very special place to visit and a beautiful place to call “home.”

Kick off the holiday season with a visit from Santa Claus, lighted Christmas parade, live music, and more!

Shop Madison County this holiday season for a hometown shopping experience like none other. In Winterset, enjoy a pancake breakfast, strolling carolers, horse-drawn carriage rides, and take part in a community canned food and winter wear drive. Warm up with hot chocolate by the burn barrels, and take home fresh greenery and locally-made items!

From 5:00 to 7:00 pm, participating stores around Winterset’s courthouse square will have live and in-motion holiday window displays, plus extended hours for your holiday shopping needs. Shopping in pajamas is encouraged!

From 10:00 am to 12:30 pm, come out to the Madison County Historical Complex for some fun with Santa Clause, photos, and cookie decorating. Complementary photos taken with Santa.

We're excited to welcome the membership to the 2018 Annual Meeting & Awards Night Banquet at the Jackson Building on the Madison County Fairgrounds on Thursday, February 1! A scrumptious meal will be served by the catering team at Hy-Vee beginning at 6:00 p.m., and a fun, relaxing cocktail party will be featured prior to the dinner at 5:00 p.m. The program and awards presentation begins at 7:00 pm. Individual tickets are available NOW at the Chamber of Commerce office for $25, or you may purchase them online. Tickets at the door are $35. Be sure to bring a little extra cash for beer and wine, as well as a chance to play Heads and Tails for a special Iowa State Fair-themed prize - tickets to see Reba McEntire on Friday, August 10, plus entry into the fair, VIP parking, and food vouchers!

Participating businesses around Winterset’s courthouse square offer chocolate samples, shopping specials and more in celebration of Valentine’s Day. No registration required, just enjoy!