Colorful old brick buildings and storefronts in downtown Princeton, Illinois, via EJ_Rodriquez / iStock.com

7 Underrated Small Towns to Explore in Illinois

When you think of the Midwestern state of Illinois, visions of bustling Chicago and endless miles of cornfields most likely come to mind. While those things make up a big portion of Illinois, it's the charming, small hometowns that dot the map and are at the heart of the state. Whether you crave an exciting getaway filled with outdoor recreational activities or a relaxing summer vacation, you'll find it one of these seven underrated towns.

Woodstock

Downtown Woodstock, Illinois.
Downtown Woodstock, Illinois.

The heart of the charming small town of Woodstock is centered around its historic town square, which was used as the setting for the Groundhog Day, a major Hollywood film. The town is best known for the Woodstock Opera House, which is one of the oldest continually operating theaters in the United States, and has showcased the work of many well-known actors over the years. Today, visitors can enjoy dance and musical concerts, lectures, visual arts shows and more in the historic venue.

Downtown Woodstock, Illinois.
Downtown Woodstock, Illinois.

Quaint Woodstock also has an abundance of natural areas worth exploring throughout the year, such as the Brookdale Conservation Area, and the Hennen Conservation Area. The town plays host to several interesting special events throughout the year, including the McHenry County Fair, the Annual Woodstock Folk Festival, and the Annual Art Tour.

Pontiac

Worn out stamp of route 66 in Tucumcari, New Mexico
Worn out stamp of route 66 in Tucumcari, New Mexico. Image credit Rawf8 via stock.adobe.com

Situated on historic Route 66 in the heart of the state, pretty Pontiac is the perfect place to spend a few days or more on your next vacation. Pontiac celebrates its interesting Mother Road heritage with a collection of Route 66 historic sites, hand-painted outdoor murals that pay homage to the famous route, and the Route 66 Museum, which features memorabilia, artifacts, historical photographs, vintage vehicles, and more.

Route 66 mural in Pontiac, Illinois.
Route 66 mural in Pontiac, Illinois.

Pontiac is also home to the Museum of the Gilding Arts, the Pontiac-Oakland Automobile Museum, and the Livingston County War Museum. Inside the town's historic courthouse, visitors will find the Livingston County Local History Exhibit. The town also delights visitors with its three unique swinging bridges, all of which cross the scenic Vermillion River.

Grafton

The Slaten-LaMarsh House, a historical building, in downtown Grafton, Illinois
The Slaten-LaMarsh House, a historical building, in downtown Grafton, Illinois. Image credit: Wikigaurabia via Wikimedia Commons.

Charming-yet-underrated Grafton is situated at the confluence of two important American waterways, the Mississippi River and the Illinois River, making it an ideal destination for water lovers. Grafton is known for its beautiful water views, which you can take in while dining al fresco at a downtown restaurant, or at one of the town's pretty parks. Taking a tour aboard the Hakuna Matata River Boat is another fun way to experience the rivers.

Port of Grafton, Illinois.
Port of Grafton, Illinois. Image credit Steve Collender via Shutterstock

For the more adventurous vacationers, a Grafton Sky Tour will take you soaring 300 feet above the town's river bluffs. For a more relaxing outdoor experience, spend some time at the Pere Marquette State Park, an 8,000-square-foot nature respite on the Illinois River. If you're visiting Grafton with your family during the hot summer months, don't miss the Raging Rivers WaterPark.

Batavia

Batavia Depot Museum
Batavia Depot Museum

Although Batavia's neighboring towns of Saint Charles and Geneva tend to get more attention, the dynamic Fox Valley destination also has more than its fair share of cultural, historical, and outdoor attractions. No matter what time of year you visit Batavia, you'll find no shortage of special events or unique opportunites, such as rollerskating at the beloved Funway entertainment complex, to keep you busy.

Fabyan Forest Preserve view in Batavia, Illinois
Fabyan Forest Preserve view in Batavia, Illinois

The town's quaint, historic Main Street is lined with one-of-a-kind specialty shops, such as the Healing Arts Metaphysical Center, delicious eateries, including the Batavia Creamery, and cafes. Walk along the majestic Fox River on one of the area's several trails, or immerse yourself in local history at the Batavia Depot Museum. The Dick Young Nature Preserve and the Nelson Lake Marsh are two must-see places for outdoor lovers.

Crystal Lake

Downtown Crystal Lake, Illinois
Downtown Crystal Lake, Illinois. Image credit Pix by Painter via Shutterstock

Cute Crystal Lake, which is located in the northern region of the state about 60 miles from Chicago, is often overlooked as a vacation destination, but it has all the ingrediants for a memorable trip. Start your visit with a relaxing walk through the historic downtown, which features a unique collection of local eateries, cafes, boutiques, and the Raue Center for the Arts, which originally opened in 1929 as a vaudeville theater and showcases live entertainment today.

The beautiful town of Crystal Lake.
The beautiful town of Crystal Lake.

If you're visiting Crystal Lake with your family, you're in luck as the town offers many kid-friendly attractions, such as the Urban Air Adventure Park. The Lippold Park Family Golf Center is another another must-experience destination, as is the North Walk Rock Climbing Gym. The Quarry Cable Park is located within the Three Oaks Recration Area on 32-acre North Lake.

Princeton

Princeton, Illinois
Princeton, Illinois. Image credit Eddie J. Rodriquez via Shutterstock

With its two charming covered bridges, the historic Red Covered Bridge, and the more modern Captian Swift Bridge, as well as an abundance of interesting attractions, the Northern Illinois town of Princeton is not to be missed. All summer long, the Down on Main street concerts delight locals and visitors alike with its live entertainment and tasty food trucks.

The historic Red Covered Bridge in Princeton, Illinois.
The historic Red Covered Bridge in Princeton, Illinois.

The eye-catching Princeton Arts District is home to several unique local shops, art galleries, cafes, and restaurants, making it a fun place to spend a day. If you want to learn more about the area's interesting history, the Bureau County Historical Society operates two local museums, as well as a well-stocked research library. Arts and entertainment enthusiasts won't want to miss the Prairie Arts Center and the historic Apollo Theater, which dates back to 1883.

Dekalb

Exterior of downtown buildings and storefronts in DeKalb, Illinois
Exterior of downtown buildings and storefronts in DeKalb, Illinois, via Eddie J. Rodriquez / Shutterstock.com

Nested in the abundant cornfields of Northern Illinois, the college town of Dekalb offers more than initially meets the eye. Dynamic Dekalb is home to the popular Northern Illinois University, which allows it to offer big-city amenities with a quaint, small-town feel.If you're visiting during the summertime, check out the Dekalb Farmer's Market, or the nearby Sycamore Farmers Market, both of which sell sweet corn and other fresh, locally grown produce and homemade goods.

Exterior of the historic Ellwood House, built in 1879, in DeKalb, Illinois
Exterior of the historic Ellwood House, built in 1879, in DeKalb, Illinois

If you love playing vintage games, you're in luck at the Star Worlds Arcade, while skaters will feel right at home at the Fargo Indoor Skatepark and Skate Shop. The historic Egyptian Theatre is located in downtown Dekalb, and offers music concerts, theatrical productions, and comedy shows all throughout the year.

The next time you find yourself traveling through Illinois, bypass Chicago and head to the state's small hometowns, where you'll find warm and welcoming communities steeped in rich history. Although many of them are overlooked for more popular destinations, they're worth checking out no matter what time of year you're passing through. Illinois' quaint towns is where much of the state's action takes place, from thriving farmers markets to exciting festivals and fairs.

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