St. Charles Town street view in St.Charles of Illinois. Image credit Nejdet Duzen via Shutterstock.

14 Prettiest Towns In Illinois

The American Midwest holds some of the most diverse and precious states, unfolding an inviting tableau of hidden gems where history, culture, and nature converge harmoniously. Illinois has been climbing the ranks of travel directories and while Chicago is its most prominent jewel, it is not where the adventure ends. While venturing beyond the cityscape, visitors will encounter quaint havens such as Nauvoo, offering echoes of the past through well-preserved landmarks and stories of yore. In these towns, history breathes through every brick and cobblestone, from Arcola's Raggedy Ann & Andy Museum to Galena's 19th-century architectural marvels. Nature is all around with locations like Long Grove's Buffalo Creek Forest Preserve. 


Mississippi River at sunset from Nauvoo, Illinois
Mississippi River at sunset from Nauvoo, Illinois.

The literal embodiment of culture is this town. Nauvoo's allure lies in its historical significance as the former home of the early Latter-day Saints community. The charmingly-preserved buildings like the Nauvoo Temple and the Joseph Smith Historic Site, upholding a piece of the town's past, are sure to catch your attention. You can also relax amid the gushing sounds of the Mississippi River and the serenity of Nauvoo State Park, a beautiful outdoor escape. Retracing the steps of driven-out pioneer saints on the Trail of Hope would push emotions to the brink, while a trip to the Nauvoo Historical Society guarantees artifacts and stories from the past. If you are looking for something to have a lazy conversation with beautiful scenery, then Baxter's Vineyards & Winery or Press House Winery would be the right choice.


Colorful old brick buildings and storefronts in downtown Princeton, Illinois.
Colorful old brick buildings and storefronts in downtown Princeton, Illinois. Image credit Eddie J. Rodriquez via Shutterstock.

Princeton has to be the master of many trades with its remarkable beauty and rich heritage, but the most prominent stands out with it being an essential Amtrak station. The picturesque Matthiessen State Park, boasting stunning canyons, waterfalls, and scenic hiking trails, is the spot for solace in nature. The Owen Lovejoy Homestead, an essential site in the Underground Railroad, showcases Princeton's historical significance and commitment to preserving its past—the Hornbaker Gardens beckon with a mesmerizing display of plants and flowers, creating a peaceful afternoon retreat. You can also check out the Bureau County Historical Society Museum, delving into the region's past. The vibrant Art District showcases local creativity, making it an ideal spot for art lovers to discover unique artworks and crafts.


The Hippie Memorial by artist Bob Moomaw in downtown Arcola, Illinois.
The Hippie Memorial by artist Bob Moomaw in downtown Arcola, Illinois. Image credit Eddie J. Rodriquez via Shutterstock.

Arcola is the "Broom Corn Capital of the World," and celebrates its agricultural roots and Amish heritage. The town's annual Broom Corn Festival is a highlight, featuring lively parades, crafts, and delicious food, providing a brief of Arcola's vibrant community spirit. The Raggedy Ann & Andy Museum pays homage to the beloved dolls' creator, Johnny Gruelle, while the Illinois Amish Heritage Center strives to conserve and display the town's Amish culture. Make your way to Yoder's Kitchen, Elizabeth Schrock Family Meals, or Hen House Restaurant to taste some Amish culinary delights. 

Long Grove

View of National Historic Bridge of Long Grove village, Illinois, USA
View of National Historic Bridge of Long Grove Village, Illinois. Image credit elesi via Shutterstock.

A vacation to Long Grove can fulfill your desire to bask in the essence of a bygone era with its historic architecture and horse-drawn carriages. The town's renowned festivals, such as the Long Grove Strawberry Festival and Apple Fest, showcase its community spirit and cultural vibrancy. The Buffalo Creek Forest Preserve is perfect for nature enthusiasts seeking a serene escape into woodlands and picturesque landscapes. Ma & Pa's Candy and the Long Grove Confectionery offer delectable treats for those with a sweet tooth. Up for some beer or wine? Valentino Vineyards & Winery and Buffalo Creek Brewing are just the spots for you. 

St. Charles

St. Charles Town street view in Elgin Town of Illinois.
St. Charles Town street view in Elgin Town of Illinois. Image credit Nejdet Duzen via Shutterstock.

St. Charles offers the ultimate Fox River getaway you did not know you needed. The town's historical significance is evident in landmarks like the Beith House Museum and the iconic Hotel Baker, reflecting the town's role in American history. Walk along the St Charles River Trail, hike or bike in the Hoscheit Woods Forest Preserve, and even embark on picturesque riverboat cruises along the Fox River. The Arcada Theatre offers live performances of plays and musicals and classic movie screenings for entertainment lovers. The Kane County Flea Market is a treasure trove for collectors and bargain hunters. Mount St. Mary Park and Pottawatomie Park offer ample outdoor recreation and relaxation.


Douglas Debate Memorial Plaza and its monument located in historic downtown in Ottawa, IL.
Douglas Debate Memorial Plaza and its monument located in downtown Ottawa, IL. Image credit Dawid S Swierczek via Shutterstock.

Ottawa is where history and natural beauty come together, and its historic district, featuring well-preserved Victorian architecture, showcases the town's rich heritage and timeless elegance. The Reddick Mansion, an iconic Italianate-style mansion, provides a glimpse into Ottawa's storied past. The town's proximity to Starved Rock State Park, offering awe-inspiring canyons and waterfalls, adds to its allure as a nature lover's paradise. Ottawa celebrates its heritage through the Ottawa Historical and Scouting Heritage Museum, home to an extensive collection of artifacts and exhibits. Washington Square Park's beautiful fountain and sculptures add to the town's allure. 


Beautiful scenic view from the West dam on Patriot`s Park Lake, near Greenville, IL. Formerly Old City Lake, constructed in 1933, is a centerpiece resource in Bond County.
Beautiful scenic view from the West dam on Patriot`s Park Lake, near Greenville, IL. 

Greenville, a warm and inviting town in Bond County, Illinois, showcases its proud heritage and small-town charm. The American Farm Heritage Museum offers a fascinating insight into the area's agricultural roots, complementing the town's strong ties to farming. The annual Bond County Fair is a highlight, where visitors can experience traditional county fair fun and revel in community camaraderie. Greenville's picturesque parks, like Patriot's Park and the golf courses of Twin Oaks Golf Course and Greenville Country Club, are the places to head for sporting activities. You can keep aside some time for the Greenville Municipal Airport's collection of vintage aircraft that appeals to aviation enthusiasts.


Part of downtown Galena with its shops and restaurants on an extremely warm day. The small town is known for its history and architecture.
Part of downtown Galena with its shops and restaurants. Image credit Ben Harding via Shutterstock.

The pretty Jo Daviess County town of Galena is renowned for its preserved 19th-century architecture. The town's historic Main Street is a living testament to its prosperous past, where you may step into Pinder Pottery & Gallery, Galena Center for the Arts, or River Bend Gallery. Galena's historical significance is evident in the Ulysses S. Grant Home and the DeSoto House Hotel, promising insights into the town's part in American history. Nature enthusiasts will be captivated by the breathtaking views along the Galena River Trail and the tranquil beauty of the nearby Galena River. For outdoor enthusiasts, the Chestnut Mountain Resort offers skiing and unparalleled views of the Mississippi River, making it an incredible place to stay during vacation.


Hollister-Balsey house in Rockton, Illinois
Hollister-Balsey house in Rockton, Illinois.

There is history, architecture, blissful nature, and buzzing festivals in  Winnebago County's Rockton. Its historic downtown gets its character from the charming buildings and friendly local businesses, like Dairyhaus, Sam's Pizza Restaurant, Sugar Britches, and Frosted Farmhouse, beckoning you to explore its unique offerings. The town's quaint setting along the Rock River provides ample opportunities for outdoor activities such as fishing, kayaking, and picnicking. It would not be wrong to say that Rockton is a nature lover's paradise with scenic trails and camping opportunities at Rock Cut State Park. The Rockton River Market is where you can head for fresh produce, socialize with the residents, and enjoy local music. The annual Old Settlers Days festival celebrates Rockton's cultural heritage and community spirit, creating a lively atmosphere for locals and visitors with live music and parades. 


Aerial drone photo - Sunrise over a rural Sycamore Illinois cornfield.
Aerial view of sunrise over Sycamore cornfield.

A vacation to Sycamore screams nostalgia for visitors with its well-preserved architecture, including Victorian-style homes and historic landmarks. Paying a visit to the Ellwood House Museum is an excellent way to discover the town's uniqueness with its exhibits, expansive gardens, and incredible architecture. The Sycamore Park District, home to the Sycamore Golf Course and Splash Fountain Splash Pad, delivers fun and recreation in one place. Sycamore's annual Pumpkin Festival is a highlight, attracting thousands of visitors to enjoy parades, carnival rides, and pumpkin-themed activities. 

Mount Carroll

The Carroll County Courthouse in Mount Carroll, Illinois, constructed 1895.
The Carroll County Courthouse in Mount Carroll, Illinois, constructed 1895.

Small towns hold the best of the things, and Mount Carroll is one such hidden gem offering everything from history to arts to natural beauty. The nearby beautiful Ayers Sand Prairie State Nature Preserve showcases Illinois' native prairie landscape of sand dunes and dry sand and wildlife, including skunk, deer, rabbit, and western meadowlark. The Timber Lake Playhouse, a renowned regional theater, offers an array of captivating performances ranging from concerts to movies to galas throughout the year. Zenga's Now&Zen Gallery is where you will find some really cool art pieces to level up your trip. The annual Mayfest celebrates arts and culture with local artisans and live entertainment.


Woodstock Square view in Woodstock Town of Illinois
Woodstock Square view in Woodstock Town of Illinois.

Heard of the iconic movie "Groundhog Day," Woodstock should be your next destination. The town is a buzzing place with its renowned farmer's markets, art fairs, summer concerts, and everything you can imagine for a fantastic getaway. Make your way to the Woodstock Opera House, a historic landmark that hosts concerts, plays, and art exhibitions. The Woodstock Fair, farmer's market, All Seasons Orchard, and Heider's Berry Farm are the stops to explore local produce, crafts, and farm life. If there is only one place you can discover, then Historic Woodstock Square is where you should set your eyes on with a stunning gazebo, eateries like D.C. Cobb's and Main Street PourHouse, the art centers of Community Room Art Gallery and Old Courthouse Arts Center. 


Country folk singer on stage street performing with guitar on red brick road during fall festival with old buildings and craft booths in background in Lebanon
Singer on the streets of Lebanon, Illinois. Image credit RozenskiP via Shutterstock.

One of the prettiest college towns in Illinois, Lebanon, lets its brick streets and McKendree University campus add to its appeal. The Mermaid House Hotel stands as a unique and historical landmark offering visitors a chance to admire the spot where Charles Dickens once had his stay. Add the nearby McKendree Metro Rec Plex to the itinerary if your interests lie in swimming, ice hockey, diving, and water polo. Horner Park is a nature spot with old trees, a vast fish pond, a nature trail, and soccer, tennis, and baseball fields.


Mississippi River aerial views of Quincy, Illinois
Mississippi River aerial views of Quincy, Illinois.

Victorian and Federal-style architecture provide a picturesque backdrop in the town of Quincy. The John Wood Mansion, once home to a prominent Illinois politician, and the Villa Kathrine, a unique Moorish-style mansion, attract architecture enthusiasts. You can choose to discover the Quincy Museum, a historic mansion turned into a museum is your shot to increase your local heritage, and All Wars Museum traces the war effects from the Revolutionary War till the present. Quincy Brewing Company and State Street Bar & Grill are your go-to for unwinding.  


The prettiest towns in Illinois offer all the attractions and experiences that showcase the state's rich history, captivating architecture, and natural beauty. From the historical significance of Nauvoo and the charming streets of Elsah to the cultural offerings of Galena and the recreational opportunities in Rockton's state park, each town has its own distinct character. Whether one is a history buff, an art enthusiast, or wishes to admire picturesque vistas, exploring these pretty towns in Illinois is undoubtedly a must. 

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