Beautiful Galena, Illinois in fall.

7 Most Memorable Small Towns In Illinois

Illinois has Lake Michigan, sweet home Chicago, the mighty Mississippi River, and scores of protected green spaces. It also has its share of memorable small towns. Whether you want to have a relaxed home base near the Windy City or desire to escape to the bucolic interior, "The Prairie State" has you covered. These seven memorable communities benefit from the friendly and elegant exteriors that the Midwest specializes in. They also meet the quota for historical places, well-utilized public parks, independent businesses, and festivals that draw impressively large crowds. So bring the noise: go discover small-town Illinois.

St. Charles

The charming town of Charles, Illinois.
The charming town of Charles, Illinois.

Though a mere 35 miles West of downtown Chicago, charming St. Charles feels a world away from the metropolitan. Instead, this small city, which belongs to both DuPage and Kane counties, has settled on either side of the Fox River. Large public parks, lengthy walking paths, cool storefronts and restaurants, and neighborly residential blocks symmetrically surround the noble waterway, creating a sense of balance and ease. But St. Charles knows how to have a good time. Every weekend, and especially during major holidays, crowds gather at Pottawatomie Park for family picnics, to play a bit of golf (mini or regular-style), or to float along the river by either renting a peddle boat or climbing aboard the St. Charles Paddlewheel Riverboat for a bit of old-fashioned fun. As the day winds down, adults can gather at one of the six local craft breweries. 

Geneva

Fabyan Windmill in Geneva, Illinois.
Fabyan Windmill in Geneva, Illinois.

For a truly memorable weekend, try following up St. Charles with a day in Geneva – just a couple of miles South down the Fox River and still within striking distance of downtown Chicago. Geneva mirrors its neighbor in a lot of ways but also injects a bit of elevated appeal. For instance, the refurbished historic downtown has over 160 independent retailers and restaurants, which pair perfectly with the 100 or so eateries and shops within the dozens of Victorian homes along Third Street. Geneva also packs plenty of green spaces along the river's shorelines. The aptly-named Island Park is a local favorite for both exercise and serenity, while the Fabyan Forest Preserve injects a bit of culture into the naturescape with a German-crafted windmill and a lovely Japanese Garden outside of Colonel George Fabyan's villa (now a museum). 

Beach Park

Illinois Beach State Park near Beach Park, Illinois.
Illinois Beach State Park near Beach Park, Illinois.

Illinois is one of only a handful of states to lay claim to the Great Lakes. In this case, it enjoys a healthy stretch of Lake Michigan's Southwestern shoreline. One of the best places to enjoy the delightfully simple beaches and swim in the fresh waters is Beach Park – a village within Benton and Waukegan townships. This laid-back, mostly residential community focuses its tourist draws to the East side. Sheridan Road, the main strip that parallels the shoreline, is where restaurants and lodging can be found. And then, on the East side of the road, a healthy dose of public-use nature spaces stretch North and South for six and a half miles. The 4,160-acre Illinois Beach State Park sits in the middle, offering beaches, trails (both dirt and paved), and a campground, with the North Dunes Nature Preserve and Illinois Beach Nature Preserve extending the zone of conservation and outdoor recreation. The windswept grass, pebbly shores, wildflowers, and sand dunes beg to be explored, but tread lightly, as over 650 species of plants rely on this area. 

Galena

Beautiful Galena in fall.
Beautiful Galena in fall.

In Northwestern Illinois, near the Iowa border, the small town of Galena preserves a wealth of classic 19th-century architecture, including the Italianate home of the former president and Civil War general Ulysses S. Grant. The Galena River, a tributary of the famed Mississippi River, bisects this seat of Jo Daviess County just minutes away to the Southwest. As a result, Galena is not short on outdoor recreation – everything from boating, fishing, and paddling to skiing at Chestnut Mountain Resort. Plus, many state parks, recreation areas, and preserves are nearby. Just don't stray too far. Galena is said to have one of "America's Best Main Streets," according to multiple authorities, including Fodor's Travel. There are 125 personalized storefronts and restaurants spread throughout the 1800s strip that will satisfy all shopping itches and culinary cravings. 

Woodstock

A scene from downtown Woodstock, Illinois.
A scene from downtown Woodstock, Illinois.

Woodstock is another small town with a quaint and engaging downtown core – so much so that it was used as the main shooting location for the Bill Murray classic Groundhog Day. Its individualized storefront facades tease books, antiques, and locally grown produce. The streets become pedestrian havens during weekend farmer's markets and annual festivals (such as the Woodstock Folk Festival and Harvest Festival). All of the action centers around the Woodstock Square Historic District, which was listed on the National Register of Historic Places in 1982. Other must-see historical buildings include the still-operational Woodstock Opera House, built in 1889, and the Old Courthouse, built in 1857, which now hosts the McHenry County Historical Society Museum. 

Ottawa

The historic Reddic Mansion and gardens in downtown Ottawa, Illinois.
The historic Reddic Mansion and gardens in downtown Ottawa, Illinois.

This small North-Central city is quite accurately said to be "In the Middle of Everywhere." Ottawa rests on the Illinois River, where it intersects the Fox River, about 80 miles Southwest of Chicago, and is but a short side-trip away from four stellar state parks. The closest is Buffalo Rock State Park, just four miles to the West. It enjoys a sandstone bluff setting and has two American bison that live on site. Next, Starved Rock State Park, which was voted as Illinois' top attraction, is just a stone's throw further West, on the South side of the Illinois River. Next up, the 1,936-acre Matthiessen State Park/Dells Area is full of pleasant hiking, horseback riding, and cross-country ski trails and features a long canyon, hikeable with waterfalls. And finally, the humble, but relaxing riverside Illini State Park awaits less than 10 miles East of Ottawa. Ottawa itself is a colorful place. Float on by the eight large murals that display the history and creativity of this memorable town. 

Fulton

De Immigrant Windmill in Fulton, Illinois.
De Immigrant Windmill in Fulton, Illinois.

An hour South of Galena, this time directly on the Eastern shore of the Mississippi River. Get a feel for Fulton and the nation's second-longest waterway by strolling some of the Great River Trail. Be sure to make a pitstop at the De Immigrant Windmill – an authentic and operational Dutch creation (one of only twelve in the United States). If you like what you see, go next door to the Windmill Cultural Center to view many other replicas and learn more about their inner workings/history. Afterward, continue up the river to the North end of town to visit Heritage Canyon. Here, visitors can get a feel for what life was like for the pioneers during the 1800s. There is a one-room schoolhouse, a covered bridge, and many other rustic, 19th-century structures spread across the 12-acre wooded park. 

Fun, fertile, and comfortingly familiar, Illinois doesn't get enough credit beyond the confines of Chicago. America's 21st state is largely made up of prairies but with magnificent bodies of water plopped in to brighten things up (namely, the Mississippi River, Fox River, and Lake Michigan). Plus, the small towns that punctuate this Midwestern region, though easy to miss, will be hard to forget once visited. So check off some of these all-American and majorly memorable Illinois towns. There is no wrong time of year to do so.

Share
  1. Home
  2. Places
  3. Cities
  4. 7 Most Memorable Small Towns In Illinois

More in Places