Downtown shops and restaurants in Galena, Illinois. Image credit Ben Harding via Shutterstock

The Best Small Towns in Illinois for a Weekend Retreat

“Illinois” means “tribe of superior men” among the Algonquin people. While the state of Illinois may not stand out as superior compared to other US states, it certainly holds its own when it comes to a handful of the best small towns in Illinois for a weekend retreat. Travelers and Illinois citizens alike should go beyond the well-known cities of Springfield and Chicago and towards the vibrant festivities towns like Galena and Geneva have to offer. You can also follow the winding Mississippi River to towns like Fulton, Nauvoo, and Alton. Choose your mode of travel or take one of the many interstate highways in Illinois toward the best small towns in the state for a weekend retreat.

Nauvoo

Downtown Nauvoo, Illinois
Downtown Nauvoo, Illinois. Image credit: Ken Lund via Flickr.com

Nauvoo is a picture of a settler’s long-desired dream of a homestead. This quaint destination on the Mississippi River has accommodated the Sauk and Fox Native Americans and, finally Mormon and Icarian immigrants from other states or from Germany. From across the river, one can visit the historic grounds of Fort Madison, while the Joseph Smith Historic Site focuses on the Latter-Day Saint movement that occurred in Nauvoo in the early 1840s. Artifacts abound in the Rheinberger House Museum, and an arsenal of historic Browning guns can be found in Jonathan Browning’s workshop. Those enthusiastic about inventions and innovations might also be interested in the Webb Blacksmith Shop with its own replica of a smithy. As for lodgings, the Hotel Nauvoo, the Inn at Old Nauvoo, and Nauvoo Vacation Villas do not disappoint.

Woodstock

Downtown Woodstock, Illinois.
Downtown Woodstock, Illinois.

Approximately 51 miles away from Chicago lies the mesmerizing small town of Woodstock. This unassuming location became famous for being the movie setting of the time-looping genre movie, Groundhog Day. Although the movie itself called the location Punxsutawney, Pennsylvania, it is undeniable to see that the precise location of filming was in Woodstock’s quotidian town square and its Gothic-tyle Opera House. Every February 2, the townsfolk celebrate the Groundhog Day festival—not for the movie, merely for the titular animals that herald the coming of spring. They also celebrate the Lighting of the Square at the start of Thanksgiving. Should you wish to relive every day unburdened by the past and unafraid of the future, then go seek out your accommodations in establishments such as the Cherry Tree Inn B&B.

Galena

Main Street of Galena, Illinois.
Main Street of Galena, Illinois. Editorial credit: Wirestock Creators / Shutterstock.com

Galena, situated close to the Mississippi River at the state borders of Iowa and Wisconsin, beckons newcomers near and far with a panoply of amenities. The Dowling House, built in 1826, is a window into the 19th-century occupations and livelihoods of Galena’s townsfolks. Meanwhile, the Ulysses S. Grant Home was a gift from Galena’s people to Ulysses S. Grant for serving well as both president and general during the American Civil War. From atop the Horseshoe Mound and other ceremonial mounds at Casper Bluff, one can get a grand view of three different states, but you can also get a better view from the sky itself during the Great Galena Balloon Race in summer. Additionally, the Galena General’s Parade on St. Patrick’s Day is also a local festivity one should not miss. If you wish to see more of Galena’s grand designs, then you ought to book a room at either the Hotel Galena, Aspen House, or A Great Escape.

Fulton

The De Immigrant Windmill in Fulton, Illinois
The De Immigrant Windmill in Fulton, Illinois. Editorial credit: Eddie J. Rodriquez / Shutterstock.com.

Fulton is full of attractions and features reminiscent of the European nation of the Netherlands. From the familiar Dutch windmill of De Immigrant Windmill to a celebration of Dutch Days on the first weekend of May, this small town on the Mississippi River and about 50 miles from Galena is truly an image of a thriving country in Europe. Aside from the cultural heritage of the Netherlands, Fulton has a number of attractions around it, such as the Heritage Canyon, where limestone mines from the 1800s attract numerous tourists who are curious about geology. The Andresen Nature Center, on the other hand, focuses on the preservation and protection of the local wildlife around Fulton. Should you ever need a place to stay in Fulton, look no further than resplendent lodgings such as the AmericInn Hotel & Suites or the Wild Rose Casino & Resort.

Ottawa

W.H.L. Wallace mural by artist G. Byron Peck in Ottawa, Illinois.
W.H.L. Wallace mural by artist G. Byron Peck in Ottawa, Illinois. Editorial credit: Eddie J. Rodriquez / Shutterstock.com.

Ottawa is an out-of-the-way paradise and reprieve for those wanting to travel 80 miles away from Chicago. With its location on the confluence of the Illinois River and the Fox River, Ottawa promises many sublime attractions and recreational areas for you to relax and enjoy. From several engaging parks and preserves like Dayton Bluffs Preserve, the Buffalo Rock State Park, and the Starved Rock State Park to biking lanes and avenues in the Fox Valley Off Road, these destinations are sure to be a far cry from all the hassle and bustle of a cityscape. The Skydive Chicago will give you an eagle’s perspective of Illinois as you skydive and parachute down to the earth. If you prefer solid ground to the sky, then you ought to tour the Reddick Mansion, home of William Reddick, who served as an Illinois State Senator. There is no need to worry about accommodations because Heritage Harbor and other lodgings will keep your belongings protected and you sound asleep.

Princeton

Colorful old brick buildings and storefronts in downtown Princeton, Illinois.
Colorful old brick buildings and storefronts in downtown Princeton, Illinois.

Around an hour away from the city of Peoria, Princeton exudes the atmosphere of a big city in a small town. From the beautiful Hornbaker Gardens to the Barn Quilts of Bureau County, Princeton’s agrarian and horticultural affinities have made the town blossom into a thriving and magnificent community. It is also patriotic, with its four Flags of Freedom commemorating the sacrifices of many a military man and woman. People from Chicago, Quincy, and Burlington board a train to Princeton’s Amtrak Train Station, a major hub for transportation between bigger communities in Illinois and beyond. Tour several historic estates and abodes like the Lovejoy Homestead or attend Festival 56, a series of Broadway or Shakespeare-inspired performances conducted by the Princeton Theatre Group. As a town lauded for being one of the most charming towns in Illinois, you can experience even more charm in fine lodgings like the Knox Hotel.

Arcola

Downtown buildings and storefronts in Arcola, Illinois. Editorial credit: Eddie J. Rodriquez / Shutterstock.com.
Downtown buildings and storefronts in Arcola, Illinois. Editorial credit: Eddie J. Rodriquez / Shutterstock.com.

Arcola, located on the Okaw River and about an hour and a half away from Springfield, was once known as Bagdad in the mid-1800s until it was renamed a few years later. Although it has no actual ties to the city of Baghdad in Iraq, Arcola certainly feels like an ancient and artistic destination with its 15 Walldog murals depicting different epochs in Arcola’s history. For years, Arcola has been a pivotal point in the Central Railroad and a prominent producer of broomcorn, hence a Broomcorn Festival every September. Interestingly enough, Arcola has had an influence in the horror genre due to Johnny Gruelle, whose creation of the Raggedy Ann Doll inadvertently created the haunting aspect of the doll Annabelle. There is more to unfold in Arcola, so stay a while in quaint abodes like the Arcola Inn or Quality Inn.

Geneva

Aerial view of Third Street over Geneva, Illinois.
Aerial view of Third Street over Geneva, Illinois.

On the Fox River lounges, a town sharing the same name as Switzerland’s most renowned city, Geneva. Only around 45 miles west of Chicago, the town of Geneva has its own Dutch windmill at the Fabyan Forest Preserve, and even more spectacular surprises at the Island Park. The Geneva History Museum chronicles much of Geneva’s early days, while Fabyan Villa Museum & Japanese Garden showcases both the horticultural and cultural values of Asia. Find even more botanical beauties at the City Hall Prairie Garden or go exploring in a Chicago 1893 World's Fair Viking Ship. From June 19 - 23, do consider attending the annual Swedish Days Festival. There are also Classic Car Shows from July to August and the Geneva Arts Fair on July 27 - 28. Do not feel so unwanted in Geneva, especially when you are resting and dining in welcoming abodes like the Herrington Inn & Spa.

Alton

Downtown Alton, Illinois
Downtown Alton, Illinois. Editorial credit: Fsendek / Shutterstock.com

Alton made its mark on history when Abraham Lincoln and Stephen Douglas held the final debate of the Illinois senatorial campaign in 1858. Additionally, Alton was the childhood home of renowned jazz musician Miles Davis and the world’s tallest man, Robert Wadlow. Those intrigued by the supernatural ought to know that Alton has the most haunted locations in the state of Illinois, as best seen in the eerie atmospheres inside the McPike Mansion, Mineral Springs Hotel, The First Unitarian Church, and Milton School. Notwithstanding this apparitional attitude, Alton is also a champion of local arts, as best seen in the Alton Little Theater, the Alton Museum of History and Art, the Jacoby Arts Center, and the Elijah P. Lovejoy Monument. Only about 18 miles north of St. Louis in Missouri, come see more of this historic town and its historic influences.

Makanda

Downtown building and storefront in Makanda, Illinois
Downtown building and storefront in Makanda, Illinois. Editorial credit: Eddie J. Rodriquez / Shutterstock.com.

The village of Makanda—whose name has constantly shifted from Markanda, Markands, and Markauda until finally settling on Makanda as a nod to a Native American chieftain—is one of those distant and remote hamlets deep in the woodlands that it might as well hail from a fairytale. But Makanda is a real place with many really grand attractions within the Shawnee National Forest. Travelers can better appreciate the beautiful and natural splendors of Giant City State Park through a few notable routes, such as the Shawnee Hills Wine Trail, the Stonefort Nature Trail, and the River to River Trail. From October 19 to 20, Makanda’s VultureFest begins with the flight of vultures that herald the arrival of autumn. Take a drink from the sweet wines of the Blue Sky Vineyard or wade in the waters of Cedar Lake. Either way, once all the excitement and exploration get you weary, settle yourself in the warm beds of Makanda Inn.

Sycamore

Downtown Sycamore, Illinois.
Downtown Sycamore, Illinois. Image credit Onasill - Bill Badzo - Have a Happy Day via Flickr.com

Sycamore trees are majestic and symbolic plants for many people worldwide. And in the heart of the Midwest, merely 60 miles from Chicago, the small town of Sycamore. Let the whimsical nature of the town pull you to one of Sycamore’s yearly events, the Witches Night Out on October 10. Feel at ease in casual picnics at the Sycamore Park District and Sycamore Lake Rotary Park. Learn of all the interesting tidbits of knowledge and history of Sycamore from the DeKalb County History Center and the Blue Moon Bikes Vintage Sting Ray Museum. You will not be sick of traveling anymore once you settle down in Sycamore’s finest establishments, such as Edgebrook.

One need not feel superior when in Illinois, but rather one ought to feel blessed and humble when visiting the best small towns in Illinois for a weekend retreat. Between the lush woodlands of Makanda and Alton’s historical significance and influences across America and beyond, you can find all manner of rare and rewarding destinations in these riveting small towns. Since popcorn is the state snack of Illinois, grab a bucket or more of these heated corns and seek weekend tranquility and rejuvenation in the best small towns in the Pumpkin Capital of the World.

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