One of the best things about Hillsboro, the county seat of Montgomery County in south-central Illinois, is that the downtown area is very compact. It’s easy to find out about anything happening in town – simply stroll down Main Street to discover what’s new. Brian Lee, who moved here with his family almost seven years ago from Nashville, has played a big role in transforming this city of about 6,000 residents into a more welcoming tourist destination.
A carpenter by trade, Lee is among a group of people who’ve been quietly transforming Hillsboro into a third-wave business community that attracts younger generations to move here. From trendy loft apartments to a record store, a brewery, a coffee roaster, local boutiques and even a nostalgic movie theater that’s been completely revamped, this is a place you have to see to believe. “The whole town feels like a cool neighborhood,” Lee says. “Everyone knows everyone – a little like ‘Cheers.’” Here’s what to check out on a visit this fall.
Opera House Brewing Company

Opened about two years ago inside a former opera house (hence the name), Opera House Brewing Company is known for its local beer and events, like its regular bourbon night. The Street Eats food truck, often parked across the street, offers food like burgers and fries that pair well with brews on tap.
We are planning a visit to Hillsboro Illinois the week of October 23, 2023.
Can you let me know if any fall events that may be happening that week?