8 Best Small Towns In Illinois To Visit In 2024

You don't hear this often, but Illinois is not the uninspiring pancake that many make it up to be. If you want to put this to the test, just fill your car's tank one weekend and take a drive on Route 66. Not to overblow it, but you will go through a delightful array of cute little towns, many of which will make for a pleasant revelation. Of course, there is Chicago, but the Windy City is a different beast altogether. If looking for areas outside of Chicago, particularly smaller towns but no less adorable —- and with plenty of stuff to see and do — this list will come in handy. Starting with Pontiac, discover the 8 best towns in Illinois to visit in 2024.

Pontiac

Pontiac presents several killer attractions and, hence, cannot be missed from a list of the best towns to visit in Illinois. It is on the legendary Route 66, a heritage that locals love and celebrate, especially via sites such as the Illinois Route 66 Hall of Fame Museum in the Pontiac Museum Complex, whose notable exhibits include the Bob Waldmire bus and van. Waldmire was a well-known traveling artist and the inspiration for the character Filmore in the movie “Cars.”

Taking the cue, the Pontiac Oakland Automobile Museum and Resource Center, the Livingston County War Museum, and the Museum of the Gilding Arts — all reveal different but fascinating aspects of the town's rich heritage and bygone era. The Livingston County War Museum, for example, is staffed by veterans, who often share first-hand accounts of their experiences. At the International Gilders Association, one will enjoy learning interesting stuff about gold leaf, particularly its use in art and industry. As for food, pay attention to Acres Inn, Lola’s, or Bob and Ringo’s, a beloved spot for pulled pork nachos.

Arthur

Arthur is home to one of the largest Amish communities in Illinois. This alone makes the town worth exploring. Amish communities are known for horse-drawn buggies, modest dressing (with bonnets), and quiet, simple lifestyles. If shopping and food is high on your list, Arthur provides an incredible experience. Yoder's Kitchen, for example, is Amish-owned and serves delicious casseroles, pot pies, chicken, and from-scratch noodles. Other options include Roselen’s Coffee, whose lattes are as great as its warm, terrific atmosphere. Shadycrest Marker’s Grill is a bright and cheerful spot that serves homemade bread and top-of-the-world deli sandwiches. Still looking for more options? Pauly’s BBQ should come in handy. On the shopping side, Arthur Mcc Thrift Shop, Yoder’s Lamps Antiques, and Winters Gallery, a cute, fun space owned by a great storyteller — are all exceptional options. Lastly, No Illinois town does fireworks before the Fourth quite like Arthur, when Jurgens Park gets enlivened by spectacular fireworks, a collage of colors, and a fun, cheery spirit.

Shelbyville

For those who enjoy the outdoors, a trip to Shelbyville is what any good doctor will recommend. Shelbyville is particularly a fantastic swimming destination. A first-time visitor can rent a pontoon boat from Lithia Springs Marina, a long-running establishment near Shelbyville, and go out on the lake to get wet or enjoy all the range of pleasure that comes with floating on Lake Shelbyville. Lake Shelbyville Visitor Center is a fun spot to prep oneself for the adventure and get some bits of necessary information. Boarmans Roxy Theater, a classic slice of Americana, is a cool, nostalgic spot to catch a mood-lifting show at dust-cheap price points. If spending more than a day, however, and want to mingle with outdoor critters in a cool, peaceful campsite, the nearby Opossum Creek Recreation Area is probably what you have in mind.

Petersburg

Petersburg reclines on the Sangamon River, just 20 miles northwest of Springfield, making it an ideal destination for a quick getaway. History buffs will love the fact that Peterburg has several associations with Abraham Lincoln. It is Lincoln, for example, who surveyed the town's platt in 1836. The grave of Ann Rutledge, ostensibly Lincoln’s first love, is near downtown Petersburg. On the grave’s headstone is an epitaph written by Edgar Lee Masters, the author of Spoon River Anthology. The boyhood home of Edgar Lee Masters, one of Illinois's most celebrated writers, is today maintained as a museum. Hand of Fate has a rustic interior, great food, and top-tier beer options, including their signature Vanilla Bean Dream. Alternatively, Broadgauge loved for its outdoor seating and live music, serves some of the best cocktails in the area. There is the county courthouse, with a display of some Lincoln papers — and Lincoln’s New Salem State Historic Site, which depicts the town as it was during Abraham Lincoln’s time. If still looking for some fun, outdoorsy stuff, the nearby Jim Edgar Panther Creek State Fish and Wildlife Area definitely deserves a mention.

Monticello

You probably know that Thomas Jefferson’s Monticello, whose gardens are a botanic showpiece, is the only private home in the United States to be designated a UNESCO World Heritage Site. This nice little town is named for Jefferson’s world-famous home; hence, a reflection of the founder's admiration for the president most associated with the Declaration of Independence. You will find a few restaurants around the square, some cute, locally owned shops, a fantastic bookstore ( the cozy Hartfield Book Company), and Allerton Park, an extensive outdoor kaleidoscope that features a 40-room mansion, natural prairie, lovely gardens, statuary, forests, and picturesque walking trails. City of Monticello Pool is a fun spot to hang out, especially if tagging kids — while the Railway Museum — with its well-restored rail cars, provides the ultimate step-back-in-time experience. The Main St Pub, right on the square, serves some wicked good burgers, while down to the south is Holly's, a good home-style restaurant loved for its homey atmosphere. What's more? One can even take a day trip to Allerton, if just to walk the gardens.

Ottawa

Ottawa has a really cute downtown, something that easily sets it apart from other Plain-Jane Illinois towns. It is also Close to Starved Rock State Park, loved for its 18 sandstone canyons, wooded trails , and seasonal waterfalls. Fox River joins the Illinois River at Ottawa, making the town a prime spot for outdoor recreation. A pleasant river walk that brings visitors right to the river's edge, is among the town's most delightful experiences. The lineup of tasty places to eat features stand-outs such as Ottawa Bakery, whose scones are out of the world. Still have more time? Do the Illinois River Road, a National Scenic Byway that follows the water for miles on end, enjoy a photo-op at the Ottawa Rail Bridge, or just explore the eye-catching murals in town, most of which depict several aspects of the town's history, including the famous Lincoln-Douglas Debate.

Galena

All seasoned vacationers know it is criminal to omit Galena from the best small towns to visit in Illinois. Galena is a good home base for exploring the Apple River Canyon State Park, a 297-acre wonderland that features deep ravines, hulking bluffs, and numerous wildlife — and the Mississippi Palisades State Park, loved for its panoramic lookout points over the Mississippi River. both of which I’d highly recommend if you enjoy hiking. Galena is in the Driftless Area of the state, where glacial floods never flattened; hence, it has a landscape that is unlike anywhere else in Illinois. Think of steep cliffs and hills, serpentine roads carved through rock, and rolling, peaceful valleys; more like driving through a Grant Wood painting. An adorable downtown area is dotted with tasty eateries such as Fried Green Tomatoes, Log Cabin Steakhouse, and Durty Gurt's, a funky joint known for its inventive burgers.

Makanda

Makanda earns a spot on the list of best towns to visit in Illinois because it is arguably the most artsy town in the state. Makanda Boardwalk, as quirky as they come, showcases the works of local artisans, including gemstone jewelry. Pop inside Visions Art Gallery, the Makanda Trading Company, or Rain Maker Studio if you want a bite-sized taste of Makanda’s artsy side. Otherwise, if you want to straddle a horse and enjoy an air-borne thrill, make plans with Rose O Sharon Equine Farm, a lovely, pastoral space that offers pasture board with run-in sheds. If wine is high up on your list, however, sample the flavors of southern Illinois grapes on the Shawnee Hills Wine Trail, especially at spots such as the Owl Creek Vineyard. Outdoor venues in and around Makanda include the lush Shawnee National Forest, Little Grassy Lake, and Giant City State Park, whose massive sandstone cliffs resemble streets of cities where giants stay, work, and move around.

The Takeaway

Except for Chicago, Illinois often gets a lukewarm reputation, especially in travel circles. Granted, The Land of Lincoln does not have the topography of Colorado, the beaches of Florida, or the Colonial history of New England. Still, there is plenty of history and culture to explore in the state and warmth and friendliness to experience in its many small towns. Looking for the best towns in Illinois to visit in 2024? Galena — and all the towns highlighted here — may reveal a side of Illinois you never knew existed. You may want to start packing. And yes, you will need a good camera.