The 11 Most Charming Small Towns in Illinois

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Whether you’re looking for a fun new vacation spot within driving distance, scouting out affordable places to live, or simply curious about what The Prairie State has to offer, a weekend getaway to a quaint small town is in order…and we’re here to help. Presenting a roundup of the most charming small towns in Illinois where the activities are plenty, the environs are scenic and the folk are friendly (albeit few). Read on to choose your next travel destination.

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Galena. Heard of it? OK, yes, you have—it has Oprah’s stamp of approval as one of the most charming small towns in the country, among other accolades—but it’s so well-known for a reason. While its streets are steeped in history (Ulysses S. Grant famously called the town home, and Lincoln and Douglas gave speeches on the balcony of the DeSoto House Hotel, which still stands today), Galena is anything but a sleepy small town. Instead, it’s bustling with wineries, galleries, ghost tours and even some gnarly snowboarding slopes.

Woodstock is famously the town where Groundhog Day was filmed, but no two days here are the same when you explore everything it has to offer. In fact, the entire downtown is on the National Register of Historic Places and can be appreciated in full with a self-guided walking tour. There are many other interesting spots to explore, too. Dip into the Woodstock Opera House to hear a jazz quartet or catch a musical, pop by one of several local farms and orchards to pick in-season produce or take a tour of world cuisines as you stroll past Woodstock’s many diverse restaurants.

What’s more picturesque than a covered bridge? Answer: Two covered bridges, and you can find ‘em just a smidgen outside of Princeton’s city limits. The historical preservation around Princeton doesn’t stop there—the old-timey main street features numerous shops and antique malls, and the town is also home to the Lovejoy Homestead, a stop on the Underground Railroad that visitors can tour for a little Civil War education. Plus, Princeton also boasts numerous scenic bike trails for the active types in your travel party.

4. Rockton, Illinois

This village near the Illinois/Wisconsin border is dotted with buildings from the 1800s, many of which feature distinctive limestone facades—including the Dairy Haus, an ice cream shop with a devoted following in the area. (Bourbon praline? Wedding cake? A scoop of each, please!) While you’re in the area, don’t forget to hop over the border—just a couple of miles away—to stock up on New Glarus beer, another treat with a cult following that’s sold only in Wisconsin. Need something other than treats to stir up some excitement? Thrill-seekers will be pleased to know that Blackhawk Farms Raceway, in the neighboring town of South Beloit, welcomes spectators of car and motorcycle races, and offers the occasional driving school if you want to take the wheel yourself; while nature lovers will delight in the nearby Nygren Wetland Preserve, which boasts numerous hiking trails and plenty of opportunities for birdwatching and wildlife viewing.

Calling all history buffs: Nauvoo, IL is a small town with a big impact on the history of Mormonism. While Joseph Smith and other prominent founding members haven’t called the city home since the late 1840’s, it’s still easy to take a trip to the past with help from an array of historical reenactors, who show off blacksmithing techniques and brick-making (you can take one home as a souvenir). Don’t miss the extensive self-guided walking tour of notable Nauvoo buildings to help your imagination travel through time, too. Your visit isn’t complete until you’ve walked the grounds of the Nauvoo Temple, either; beyond its beautiful design, this stately building also happens to be the only LDS-owned temple with a bell tower. And if you feel like spending some time in nature, some gorgeous scenery—a pristine lake surrounded by woods—awaits at Nauvoo State Park, too.

Nearby Starved Rock State Park may steal the spotlight from Ottawa, but it’s well worth trekking into town after you’ve finished your hike. Studded with well-maintained Victorian homes (and with the requisite charming downtown you’d expect on this list), Ottawa puts its own twist on the small-town experience with an abundance of modern murals to mix the old with the new. And if you need a snack to power you through another round of Lincoln/Douglas historical sites, keep an eye out for the beloved Popcorn Wagon, a relic from the 1890s that still serves up fresh, salty kernels.

Quincy is chock full of fun activities: Take yourself on a driving tour of the city’s smattering of mid-century modern homes, or follow this guide to public art installations, which also includes tips on where to grab curbside food and drink as you go, so you can create your own combination art and pub crawl. Had your fill of murals and snacks? Check out one of the prime lookout spots for seeing bald eagles when they spend the winter in the area. But even if you manage to see every home, mural, and fowl in Quincy, you’re still in luck: Hannibal, MO—and its treasure trove of Mark Twain attractions—is just half an hour and a hop across the Mississippi away.`

Fulton provides another opportunity to step back in time, but with a distinctly Dutch vibe. Admire the city’s prominent windmill, brought over from the Netherlands, and pop into the gift shop to take home the buckwheat, rye, and other grains ground on-site. From there, take a walk through Heritage Canyon, which is home to pioneer-era structures such as a one-room schoolhouse and a covered bridge. If you’re in the mood to live in the moment instead, explore your options for boating and fishing along the Mississippi River.

9. Lebanon, Illinois

This is Illinois’ OG college town: McKendree College is the oldest in the state. There’s plenty to learn about even off campus, from the histories of the city’s buildings (a surprising mix of Southern Colonial, Greek Revival, Gothic and other styles) to the Emerald Mound, the preserved remains of a Native American village and effigy mounds. Is that not enough history for you? Check out the Mermaid House, a former hotel visited by Charles Dickens, who later name-dropped it in American Notes.

These delightful villages sit just a few miles apart on Highway 133 in Illinois’ Amish country, and if you’re going to visit one, it would be a shame to miss out on the other while you’re so close by. Arcola may be slightly better known, as it’s where the Raggedy Ann doll was first invented around the turn of the 20th century. Another site to see in town? The “World’s One and Only Hippie Memorial,” a public folk art installation dedicated to the tumult of the 1960s. Meanwhile, in Arthur, The Great Pumpkin Patch awaits with 300+ varieties of squash and gourds grown on-site, plus a variety of baked goods to snack on while visiting the farm’s llamas, exotic chickens and other animal residents.

This Henry County gem is easily accessible—the famous Route 6 runs right through it—and boasts a number of low-key attractions, including a particularly quaint and old-timey downtown strip, numerous residential enclaves featuring impeccably restored Victorian homes on tree lined streets and a picturesque river and canal just outside of town where tubing, fishing and kayaking opportunities abound. There’s also a historical museum devoted to the town’s past as an underground railroad hideout, plus 100 acres of green parkland to explore and five different playgrounds for those traveling with kids in tow. Bottom line: If you’re looking for a quiet stay with boatloads of Norman Rockwell charm, Geneseo is hard to beat.

purewow author

Freelance PureWow Editor

purewow author

Freelance PureWow Editor

Emma Singer is a freelance contributing editor and writer at PureWow who has over 7 years of professional proofreading, copyediting and writing experience. At PureWow, she covers...