WINCHESTER’S MUSIC in the Park begins 11th season

By Editor | June 10, 2026 |

By Carmen Ensinger

It is hard to believe, but it has been 11 years since an idea was born to provide free weekly entertainment during the summer on the Winchester Square, also known as Douglas Park.
The city is blessed with a wonderful park in the heart of downtown and the Winchester Civic Group, who is always looking to bring folks into town, and others were looking for something to compliment a newly organized Farmer’s Market that was starting.
Folks could come get their fresh veggies, if so inclined, and then stay for some free entertainment afterwards. Or, just bring their lawn chairs up, set them up in the shade under a tree and wait for the music to start.
Nothing much ever goes on during the middle of the week, so it was decided that Thursday would be the day for both the Farmer’s Market and Music in the Park, and nothing has changed in the last 11 years, up until this year.
“We are shortening the concert season this year by a couple weeks with our last concert on July 16, ”John Paul Coonrod said. “In the past we have gone through the end of July and into the beginning of August, but we have found that when you get close to the end of summer, people are squeezing in their end of summer vacations and gearing up for the start of school. Plus, it is unusually unbearably hot around this time as well.”
Coonrod said the concert series is a collaborative effort between himself and Stuart Smith.
“We really don’t have any sort of title,” he said. “We do everything from selecting the bands, to booking the bands, to raising the money to pay for the bands and even putting together the food service that will be served that evening. After 11 years, we have the system down pretty good.”
As for raising funds to pay for the entertainment, Coonrod said half of the funds are raised through sponsorships from local businesses and the other half from food sales before the concert and during the first half.
“There is no overhead,” Coonrod said. “All of the money raised goes for paying for the bands.”
Various church groups, friends and members of the Winchester Civic Group generously donate their time every year to cook and serve the food and take the money, which then goes to pay for the bands.
The concert series began on Thursday, June 4 with Ben Bedford and will continue through July 16 with a wide variety of different musical genres.
On June 11, they’ll welcome Tom Irwin and Amy Battles to the stage.
“They have played our ‘Music in the Park’ series several times and get invited back every year,” Coonrod said. “Mainly because they give a great blend of folk music and story telling.”
On June 18, the concert will be – “Blue and Greene: A Jazz Tribute to Rob Killiam.”
“This is going to be a homage to Rob, who was a local jazz musician and all around very pleasant man,” Coonrod said. “He passed away suddenly two years ago and this concert will be a jazz tribute to him.”
The following week, June 25, they’ll welcome back Reverend Robert.
“Robert will be coming back up from the Mississippi Delta to give us his special blend of Delta Blues and Calypso rhythms,” Coonrod said. “He is another regular at the summer series every year because he just gives a great show and we are looking forward to having him back.”
Bringing in the month of July, the Two Fiddles Band will be playing on July 2. This group of classically trained Springfield musicians will bring a selection of classical and traditional national and American music.
On July 9, Chris Valillo will take the stage to present “America at 250: The Power of Democracy in Song.”
“Chris will be giving us a selection of songs from the entire history of the United States,” Coonrod said. “For each song, he will give us some details and stories behind that song – a kind of narrative of American history presented in song.”
The last and final concert of the summer will be the Silver Creek Bluegrass Band on July 16.
“They are a bluegrass band based out of Edwardsville and I just can emphasize what a wonderful show those guys put on,” Coonrod said. “They have been invited back several times now, and I look forward to having them round out our season.”
Coonrod encourages everyone to come to at least one show, preferably all of them this season.
“I encourage everyone to come out and enjoy the company of their family, friends, neighbors or anyone else they choose,” he said. “Bring your lawn chairs, enjoy some food you don’t have to cook and catch a live show.”
Coonrod had one last piece of advice for anyone coming up – bring some bug spray for the gnats.