Illinois, featuring one of the most mundane nicknames, the Prairie State, is anything but boring. It is home to dramatic terrain and a slew of quirky towns with captivating history, many green parks, and riverside trails for nature lovers. The only monotony in Woodstock comes from the screen, whereas in life, this small town set for the Groundhog Day film is a quirky-to-the-core party destination.

　　An old mining town in Illinois' northwest corner, Galena, home to a former US president, is a touchstone for the area's most significant 19th-century architecture, with outdoor recreation at Horseshoe Mound Preserve and its Galena Cellars Vineyard. You can find more rich history in Quincy, while Elmhurst, just thirty minutes from Chicago, feels a world apart with its tree-lined streets veiling spectacular cultural institutions!

　　Illinois Destinations for 2024Visit the eight best towns in Illinois in 2024

　　

Arcola

Downtown building and storefront in Arcola, Illinois, USA. Editorial credit: Eddie J. Rodriquez / Shutterstock.com This small town is a fantastic weekend trip idea for adventurers with a hobby to explore new, scenic small towns with an old-timey charm! Arcola, where the Raggedy Ann doll was first created, is home to under 3,000 locals who love to host unorthodox festivals, which makes it one of the quirkiest towns in Illinois. Its famous celebration called the Broom Corn Festival explodes the population with tourists wishing to partake in free, fun, family-friendly events, entertainment, and excellent local cuisine! Staying quaint is not in Arcola's character with other festivals like the Raggedy Ann Festival, the Horse Progress Days, the Amish Country Bicycle Tour, and Oktoberfest!

　　Keep the vibe going at the Hippie Memorial and the Instaworthy Illinois’ Original Burger King from 1952, while the more conventional attractions include the Green Mill Village Theatre and Arcola Presbyterian Church. Isolated from the bigger cities in the state's Amish country, Arcola epitomizes escaping the bustle into an idyllic, slow-paced farm lifestyle. From ancient horse-drawn buggies through town to the expansive surrounding corn fields with picturesque red barns, there's no better place to make family moments count over feel-good pursuits. Visitors can enjoy browsing through the iconic Carnegie Library, pick up a locally crafted raggedy doll for themselves, kids, and friends back home, and tud-on some Amish fudge along!

　　

Elmhurst

Elmhurst University, a private liberal arts institution in Elmhurst, Illinois, USA. Editorial credit: Joseph Hendrickson / Shutterstock.com Just thirty minutes inland from Chicago, Elmhurst feels a world apart, delighting tourists and day trippers with a small-town feel and celebratory atmosphere along its tree-lined streets. This enticing little community of retail shops and fine dining features an outstanding cultural landscape with theater, art, and excellent museums. The Romanesque Revival profile of Elmhurst History Museum houses rich and colorful history through exciting antiques, artifacts, and temporary exhibits. From a morning run or bike ride down the pastoral 37-mile Illinois Prairie Path to engaging year-round events, you can revel in classical music like Mozart, Beethoven, and Mahler at the Elmhurst Symphony Orchestra.

　　Elmhurst City Centre, part of the vibrant downtown, features urban boutiques, live music, and movies, while the family-friendly Wilder Park is home to the Elmhurst Art Museum with modern art and Mies van der Rohe-built and designed McCormick House. Many come to Elmhurst for its iconic windmill but linger for family-friendly Berens Park and Sky Zone Trampoline Park or party destinations. With entertainment joints that make this small town a community hub with a lot of character, like Riley’s Gathering Place, Pints, Fitz’s Spare Keys, and Drury Lane Theatre & Events, it is a perfect long weekend of fun. Don't miss the Drury Lane Theatre & Events and the Lizzadro Museum of Lapidary Art, a gallery of gemstone treasures!

　　

Fulton

The De Immigrant Windmill on the Lincoln Highway in Fulton, Illinois, USA. Editorial credit: Eddie J. Rodriquez / Shutterstock.com Fulton, quaintly sprawling along the river banks of the Mississippi, boasts pronounced Dutch roots. It is a popular small-town destination to experience the feel of a foreign place where the river views and water pursuits add to the charm! Visitors can dive into the intriguing history at the Windmill Cultural Center and the Sawmill Museum, and don't miss the Andresen Nature Center and Heritage Canyon for local nature, including the canyon's walking tour. There's no better way to get first-hand experience of traditions and taste the modern lifestyle than the first May weekend during the Dutch Days Festival, and treat your friends back home to the memories they couldn't partake in with gifts from Great River Road Antiques!

　　Welcoming most visitors during this festive time for the parade, music, food, and make-your-own arts and crafts, the crowds don't die until well into the fall, with the refreshing river and all luring tourists to waste away their summer vacation days here! Named after Robert Fulton, the steamboat inventor—part of the riverfront intrigue—you can visit anytime for pretty sights and exciting attractions in Fulton, one of the coolest towns in Illinois. Famous for its fully operating windmill, visitors can enjoy this authentic landmark with the wistful name “de immigrant," once delivered straight from the Netherlands, and buy freshly milled flour at the nearby gift shop!

　　

Galena

Main Street in the historical downtown area of Galena, Illinois, USA. Editorial credit: Dawid S Swierczek / Shutterstock.com Are you yearning for an epic weekend getaway with fun attractions to release your inner quirkiness? This beautiful town, overlooking the Mississippi River, will meet and exceed your expectations as a high-level ground recreation spot for families and couples. Galena's scenic banks are perfect for strolls, adventures, and picnics under the summer sun, while the awe-inspiring Horseshoe Mound Preserve will strike down historians and avid nature lovers alike! Adjacent to it, the striking Thunder Bay Falls is perfect to spread a blanket under with a bottle of wine from one of Galena's great wineries! This highly sought-after town keeps tourists, locals, and new residents on their toes with a dynamic scene of plentiful restaurants and bars.

　　While here, in the home of the former US president, Ulysses S. Grant, you don't want to miss his house, open tours, and another notable stop, the Old Market House State Historic Site from 1845, now a museum! Home to several other Union generals during the Civil War, this old mining town in Illinois' northwest corner is a real touchstone for the area's most significant 19th-century architecture! With 800 buildings on the National Register of Historic Places, including the 1800s samples along the main street, you can experience it all while shopping around, as well as learn how Galena was named after a mineral from the area!

　　

Lebanon

A country folk singer performs on a street stage during a fall festival in Lebanon, Illinois. Editorial credit: RozenskiP / Shutterstock.com Borrowing its name from an Asian country, Lebanon is a gorgeous college town in St. Clair County, home to McKendree University. With its oldest college in the state, intriguing, rich history, and destination milling, distilling, and brewing sites, Lebanon is a perfect new town to explore, with quirks for every taste! Boasting several world-class hotels, make it a peaceful and relaxing weekend escape with discoveries by day and cultural evenings over live performances at the Russell E. and Fern M. Hettenhausen Center for the Arts! There is so much to discover here, like the central historic district split over five main areas, so get caffeinated and start along the university grounds.

　　Just north, Horner Park, with its pristine nature around a scenic pond, feels even more removed from any signs of civilization, except for its Horner Park Hall and a playground! You are bound to wander into the Emerald Mound and Village Site, an Instaselfie place, swipe away along Brick Street, the designated shopping center, and make a detour to the satellite village of Cahokia, an archeological site and settlement, for significant Mississippian culture. Are you still wondering about the name? Driving around or checking your maps will reveal other Middle East-named towns, all due to the confluence of the Mississippi and Ohio Rivers—a lookalike to the Nile Delta!

　　

Quincy

Aerial view of the Mississippi River near Quincy, Illinois. Impressed with the area's timber and fertile soil near a natural harbor, John Wood, the area's first European settler, purchased a 160-acre bounty for $60 along the Mississippi River. Having begun as a small trading community under the name of Bluffs, in 1825, state commissioners took a tour around its public square—John's Square, today—naming it Quincy in honor of the newly-elected U.S. President, John Quincy Adams. Quincy was incorporated in 1840, with the city's earliest settlers arriving from New England in what was, by then, an economic boom town with a varied labor workforce and transportation of locally made goods. The climate and rich soil in the river area sprung up agriculture and farms, while the native forests and riverboat industries bequeathed it “The Gem City.” 

　　With 30,000 locals by the end of the mid-century, including immigrants from political turmoil in Germany, Quincy would soon attract tourists for favorable outdoor activities. Today, the town of natural bounty between the river and farmland is a passionate community with art and architecture, an up-and-coming culinary scene, and, clearly, a notable history. Visitors can enjoy welcoming festivals, events, and year-round self-guided explorations, with a must-stop at Quincy Museum and the Villa Kathrine, an unmissable building for its Mediterranean appeal. The town's pretty, historic vibe is epic through its South Side German Historic District, where the architectural styles range from German influence to Prairie-style designs by Frank Lloyd Wright!

　　

Woodstock

Street view in Woodstock, Illinois, USA. Editorial credit: Nejdet Duzen / Shutterstock.com This small town, a big star of unproportionate character, is forever immortalized in Bill Murray's 1993 movie, Groundhog Day, primarily filmed in Woodstock! Letting tourists invoke thrilling memories on a stroll-through, you can feel part of the set, mingling with the locals and sightseeing along the Woodstock Square Historic District! Woodstock, where no two days are unlike the movie plot, delights history buffs and cinephiles alike, while friends on a weekend to party should look no further than its stops like Winestock Market & Lounge, Liquid Blues Ltd., and Orttoman’s Red Iron Tavern. Meanwhile, families seeking a quiet escape can let the little rugrats go wild at Woodstock Water Works!

　　Entirely on the National Register of Historic Places, the downtown area brims with various cuisines and a slew of shops where you can pick out handcrafted jewelry, unique gifts, and fine arts to bring home. Don't miss the jazz quartet at the Woodstock Opera House, an unmissable historic centerpiece from 1889 featuring a Carpenter Gothic and Moorish profile! From strolls along the brick streets to seasonal markets and local farms worth exploring on a scenic drive, planning your trip for Groundhog Day may just be the best decision you make this year! The town's mascot, Woodstock Willie, takes the front stage in Woodstock, even though Groundhog Day actually took place in Pennsylvania.

　　

Discover Illinois' Quirkiest Gems

Home to small, beautiful towns, the best of which are quirky to the core, Illinois is a magical destination you don't want to miss, with dramatic terrain and stunning views of the mighty Mississippi River on the west side of the state! So pick up a raggedy doll where it was invented in the first town of Arcola and explore the “Land of Lincoln,” a midwestern state full of opportunity through its charming gems.

　　Elmhurst is home to the Lizzadro Museum of Lapidary Art, a gallery of gemstone treasures, while Quincy was the state's "Gem City" for its riverboat and forest industry, which turned the town upside down soon after German immigrants settled the South Side German Historic District, an architectural neverland including works by Frank Lloyd Wright!

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