Hillsboro has historic homes, new development and lake access
Surrounded by greenery, open space and farmland, Hillsboro is a quiet, rural city serving as the county seat of Montgomery County. Century-old homes are scattered throughout the downtown area, where the Historic Courthouse Square often operates as a community gathering place. “Hillsboro has come a long way in the last couple of years, and we still have a lot of things we plan on doing,” says Melissa Smith, economic development and community planner for the City of Hillsboro, who also sells with MCR Realty Professionals. “There has been an increase of businesses that have come to the area, and a lot of development.”
Single-story homes spanning decades and centuries
Most homes in Hillsboro are found along tree-lined streets with grassy lawns and alleyway access. Traditional single-story homes and bungalows built between the 1900s and 1960s are common close to downtown. The area also has ranch-style homes from the 1960s to the 1980s. These smaller properties cost between $40,000 and $180,000, depending on age and condition. Multistory Victorian homes are also popular, sporting simple exteriors, a steep pointed roof and a front porch. Colonial homes are another option. Prices range from $100,000 to $220,000.
Outside the city limits are larger properties that sit on acreage. Midcentury, ranch-style homes and raised ranches go for $150,00 to $500,000. “We do have housing on the lakes. A lot of people from the Saint Louis area whose boats aren’t big enough for those lakes, they come here for their second homes because its close,” Smith says.
Staying active at city parks and lakes
Central Park is the city's primary recreational space. It has an all-inclusive playground, three pickleball courts, a basketball court and a field for baseball. Most of these facilities were recent additions from community fundraising in 2024. The Central Park Pool offers daily and seasonal passes. Across the street, Challacombe Park is the site of the historic Challacombe House, which was built by Hillsboro’s first mayor. The area also has a fenced-in dog park and walking paths.
Hillsboro’s proximity to two lakes is a huge draw for outdoor enthusiasts. Lake Hillsboro is about 2 miles northeast of the city and is referred to as “the old lake” by locals. A park area on its northern shoreline has picnic pavilions and a public boat launch. “There is a 10-miles-per-hour speed limit, so it’s more of a leisurely fishing lake,” Smith says. Nearby is the Sherwood Forest Campground, which has over 125 camping sites. The Hillsboro Country Club is also located along Lake Hillsboro and has a private 9-hole golf course. Farther north is Lake Glenn Shoals. Its North Access Area sits adjacent to the Meisenheimer Avenue Bridge, roughly 6 miles away, and is outfitted with two boat launches, a fishing dock and a kayak launch.
Shopping and dining downtown and along Main Street
Downtown Hillsboro starts at the courthouse square and continues down Main Street. There are dozens of small businesses, gift shops and specialty stores – The Sweet Spot is a candy shop, and The Story Emporium sells books. Hillsboro Garden Family Restaurant is a casual eatery specializing in comfort food. More options are found farther south as Main turns into Vandalia Road. The Smokin Barrel is a newer restaurant serving barbeque. Capri Market is the area’s grocery store. Fast-food options include McDonald’s, Dairy Queen and Hardee’s.
The Hillsboro Farmers Market takes place on the second Saturday of every month during the summer, selling local produce, baked goods and handmade products.
Getting educated at Hillsboro public schools
The city is served by the Hillsboro Community School District. Beckemeyer Elementary School earns a B-minus grade from Niche and offers an afterschool program. From there, students attend the B-rated Hillsboro Junior High School. Hillsboro High School receives a B-minus and offers a teaching internship for students participating in the Child Care Career and Technical Education program. For higher education, Lincoln Land Community College has a satellite computer lab in Hillsboro, which is connected to the Litchfield outreach campus.
Celebrating Hillsboro’s annual community events
Multiple events are celebrated in Hillsboro. The Annual Harvest Market is a festival held at Hillsboro’s Historic Courthouse Square in October, featuring handmade and homegrown products. The event also has live entertainment and a cornhole tournament. Hillsboro’s annual Small Town Christmas sets up a holiday-themed vendor market, petting zoo and carriage rides. “They’ll close downtown off and do a block party, and they’ll have fake snow,” Smith says. There are also contests for cookie decorating and gingerbread house building.
Driving in and around Hillsboro
Hillsboro’s rural landscape requires a vehicle to navigate. Illinois state Route 127 is the city’s main thoroughfare, traveling north and south. The road merges with Illinois state Route 16 in the city, which commuters can use to reach Litchfield to the west and Vandalia in the southeast. Hillsboro Health is the area’s general hospital, located along Tremont Street. The Abraham Lincoln Capital Airport is roughly 54 miles away in Springfield.
