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.
Orpheum Theatre

You can’t beat the $8 movie deal at the historic Orpheum Theatre, which includes admission, popcorn and a drink. The Eisentraut family operates the theater, and they know their customers well. For big premieres, they’ll often dress up or have a display of some kind, Lee says. For example, during a Harry Potter movie, they served butterbeer. It’s a different kind of experience that “doesn’t feel like you’re just paying to see a movie,” he says.
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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?