With Halloween just two weeks away, spooky season is in full swing. Whether you like to watch seasonably appropriate horror films or enjoy the opportunity to go out in a costume, Halloween has a little something for everyone. In Brookfield, that includes an opportunity to stop in at local businesses downtown for trick-or-treating a few days before you might do the same around your neighborhood.

On Oct. 26, the Saturday before Halloween, the Brookfield Historical Society and Brookfield Chamber of Commerce, in partnership with the village, will host the 25th annual Monsters on Mainstreet event. From noon to 3 p.m. that day, kids are encouraged to stop inside participating businesses along Grand Boulevard and Broadway Avenue to trick-or-treat and meet the friendly faces who operate the stores.
Once trick-or-treating is over, there will be a costume contest for kids at the Grossdale Station, 8820 ½ Brookfield Ave. at 3 p.m. and free apple cider, taffy apples and pumpkins for the first 500 or so kids to arrive, starting at 2:30 p.m. The contest is split into four groups for kids ages 4 years and under, 5- to 8-years-old, 9- to 12-years-old and 13 years and up. Within those groups, kids are eligible to be recognized for the funniest, scariest and most creative costume.
While Monsters on Mainstreet may now feel like a yearly staple to Brookfielders, the event got its start in just 1999, said founder Kit Ketchmark, who has remained the driving force behind it all these years. Now a village trustee and director of the Brookfield Historical Society, Ketchmark told the Landmark that Monsters on Mainstreet originated as a family-friendly way for the village to promote its local businesses.
“Back in 1999, the village was applying to be a Main Street community with the state. That’s an economic development program they had going on for helping small towns [with] community development,” he said. “One of the parts of that program was a promotions committee, and I was the co-chair of that committee.”
Ketchmark said the committee conceived of the event as a way to introduce families in town to the stores in the central business district, which weren’t as plentiful as they are today.
“We had an awful lot of open store fronts back then, and there wasn’t a lot of activity downtown, so we decided trying to do something on Halloween,” he said. “The way we did it the first year is, we would have volunteers. People would meet at the Grossdale Station, and then one of our volunteers would actually lead a parade through the downtown area, and they’d go store to store to store.”
Ketchmark said there were four starting points around town that first year with volunteers to lead kids around. Still, “that idea is about almost the only thing that’s changed over all the years,” he said. That format meant each trick-or-treater in a group would arrive at the same store at the same time, inundating it with children before they all moved on together and left it with no visitors. In the years since then, the event has followed a more open plan where families can trick-or-treat at their own pace and in whatever order they want.
While the event got its start under Main Street Brookfield, Ketchmark said the organization shuttered soon after, which is when the Brookfield Historical Society took on the mantle.
“The Chamber of Commerce, at that time, wasn’t very active at all. Not a lot of membership,” he said. When the winds shifted and the chamber became more active, it joined the historical society as a sponsor. The two organizations ran Monsters on Mainstreet themselves until the village joined in just a few years ago, and the three have been partners since, Ketchmark said.
Over the years, he added, the event’s volunteers have gotten good at knowing how many people to expect and how to organize them, especially when it comes to the post-trick-or-treating festivities.
“The in-store count of kids is over a thousand,” Ketchmark said, though the total number of people can exceed 2,000 with parents tagging along.
He said trick-or-treating usually comes to a natural end around 2 p.m., even though it formally runs for another hour; at that point, people start waiting for the costume contest, with the line starting at the Grossdale Station’s front door and often wrapping around the block and up Forest Avenue.
Ketchmark said Monsters on Mainstreet has remained a strong event to introduce residents to downtown businesses, of which about 90% now participate, over the years.
“You get a lot of residents who go to these stores and [say], I didn’t know that was there, or I’ve never been in there, or whatever, and then they come back to shop there, return there, maybe have lunch there,” he said. “That was the whole idea of it. It’s fun and all that, but it’s an economic development tool to spur interest in the downtown areas.”
When Monsters on Mainstreet first began, Ketchmark said he wasn’t sure whether people would be interested in it, but these days, most attendees walk the entire distance from the Grossdale Station to the businesses near Eight Corners. He said one of his favorite parts of the event is the way it’s fostered community in Brookfield between residents.
“That’s a pretty good distance, and people just come out and hang out,” he said. “It’s really fun seeing the young parents [with] their young children who say, ‘I did this when I was little,’ and now they’re here with their own kids.”






