Historical Galena Town view at Autumn in Illinois.

The 7 Most Picturesque Small Towns In Illinois

When people think of Illinois, the bustling city of Chicago most likely comes to mind. However, the Midwest state is also filled with charming, picturesque small towns in every region. Some are college towns while others are quaint farming villages, but all have a uniqueness that set them apart from one another. Whether you are looking for a relaxing respite from everyday life or an exciting outdoor adventure, you are sure to find it in one of these small Illinois towns. You can make one of these picturesque towns your vacation destination, or a stop along your journey to Chicago or other locales.


Historical Galena Town Main Street in Illinois
Main Street in Galena, Illinois. Image credit Nejdet Duzen via Shutterstock

Situated on the Mississippi River, Galena boasts stunning water views, rolling hills and bluffs, history, top-notch restaurants, and charming boutiques. Galena's downtown beckons shoppers with its collection of eclectic stores, many of which are in historic buildings. No matter what time of year you visit Galena, you will find a special event, such as a festival or farmer's market, to keep you entertained.

History buffs will not want to miss the Ulysses S. Grant home, which was offered to the 18th US president upon his return from the Civil War in 1865. The US Grant Home State Historic Site showcases many of the president's original furnishings and personal photos. Located in downtown Galena, the historic DeSoto House Hotel is Illinois' oldest operating hotel and features three restaurants and banquet facilities for special events. For outdoor lovers, the Galena River Trail offers an 8-mile path, plenty of scenic views, and picnic tables. Launch a canoe or kayak at the Galena Boat Dock, and spend a day immersing yourself in river wildlife. If you don't own a boat, you can rent one at one of Galena's rental outfitters.


Red Covered Bridge, An Old covered bridge near Princeton Illinois
An Old covered bridge near Princeton Illinois.

Even though Princeton is a small town, it is home to not just one, but two covered bridges. Located in northern Illinois, Princeton has a history dating back to the mid-1800s when settlers arrived due to the area's rich farmland. Throughout the year, Princeton plays host to several special events, such as the Homestead Festival, a farmers market, and the Covered Bridge Quilt Show.

When visiting the area, do not miss a trip to the town's Red Covered Bridge or the Captain Swift Bridge, which is also covered. One of only five remaining historic covered bridges in Illinois, The Red Covered Bridge was built in 1863 and crosses Big Bureau Creek. It is on the National Register of Historic Places and has long provided inspiration for artists. Spend a day at Princeton's Alexander Park, which features sprawling grassy areas, a 9-hole disc golf course, sand volleyball, a playground, and an outdoor pool. Zearing Park offers horseshoe pits, picnic shelters, a walking path, and a 3-acre fully stocked pond.


A view of the Illinois River at Starved Rock State Park, Oglesby Illinois.
Illinois River at Starved Rock State Park, Oglesby Illinois. Image credit WhiteBlush via Shutterstock

Also situated in northern Illinois, Oglesby is home to the famed Starved Rock State Park. Not only is Oglesby's Starved Rock State Park a well-known destination for Illinois nature lovers, but it also welcomes visitors from all over the country and even the world as well. The expansive park spreads along the Illinois River and has a rich Native American history. Starved Rock features 13 miles of hiking trails, bluffs, waterfalls, and several scenic river overlooks. The park's historic lodge offers souvenir shops, indoor and outdoor eateries, and rooms for visitors who want to stay overnight. Rustic onsite cabins are also available.

The charming town also offers other local parks, outdoor recreation, historic sites, shopping, and a quaint downtown to explore. During the warm spring and summer months, launch a raft, canoe, or kayak from the Vermilion River Boat Ramp. You can also rent boats or sign up for tours on the Illinois River while in Oglesby. The city offers the Deer Park Golf Club featuring an 18-hole golf course as well.


North aerial view over Island Park in Geneva, Illinois
Island Park in Geneva, Illinois.

One of Chicago's far western suburbs, Geneva delights locals and visitors alike with its charming, historic downtown and many opportunities for outdoor recreation, shopping, and dining. Situated on the Fox River, Geneva offers scenic views year-round. The crown jewel of the city, downtown Geneva offers more than 160 specialty and antique shops, boutiques, casual cafes, coffee shops, gourmet chocolate retailers, and restaurants. There are plenty of places to enjoy an outdoor lunch or dinner during the warm months, as well as a train station for those who want to take a fast trip into Chicago. Downtown Geneva also plays host to several events and festivals, such as an art fair, throughout the year.

If outdoor recreation is more your thing, bring your bike or rent one from a local shop, and explore the 40-mile Fox River Bike Trail, which meanders through Geneva. Spend a day at the Fabyan Estate and Forest Preserve, which features a restored historic villa, Japanese gardens, and a 19th Century Dutch Windmill.


Downtown building and storefront in Makanda, Illinois
Downtown Makanda, Illinois. Image credit Eddie J. Rodriquez via Shutterstock

Located in the southern region of the state, Makanda is a true small town with less than 600 residents. What the village lacks in population, however, it makes up for in natural beauty and history. Known by some as Illinois' "most hippie town," Makanda hosts the annual Vulture Fest in October.

Visit the Giant City State Park, which features hills and ravines, waterfalls, and miles of rustic trails. Golfers won't want to miss Keller's Crossing at Stone Creek, an attraction featuring a 235-acre golf course and a restaurant. The Blue Sky Vineyard is a world-class winery located in the Shawnee National Forest. Featuring eye-catching Tuscan decor, a scenic forest view, and an onsite eatery, the winery is available for overnight stays and special events. Shoppers will be in heaven at the Makanda Boardwalk located in the historic downtown. The boardwalk offers several shops, art galleries, and eateries.


Aerial View of Downtown Woodstock, Illinois during Summer Twilight
Downtown Woodstock, Illinois.

Located 45 miles northwest of Chicago, the quaint town of Woodstock offers a picturesque town square with an authentic hometown feel. Known for its historic sites and rich arts and culture scenes, Woodstock makes a good place to both play and stay. The focal point of the town square, the world-famous Opera House,  built in 1889, has had many famous actors on its stage over the years. It still offers a revolving roster of well-known musical acts and theatrical shows and is also available to host special events. If you are visiting the town in July, do not miss the annual Woodstock Folk Festival.

Explore local nature and wildlife at the Brookdale Conservation Area, where a 1-mile grass trail loops around a pond and an observation deck overlooking a former pine plantation. During the summer months, visit the Dented Gate Flower Farm to pick your own blooms and make your own floral arrangements onsite.


Windmill on Bike Path in Fulton Illinois
Bike Path in Fulton, Illinois.

Nestled against the Mississippi River directly across from Clinton, Iowa, the charming waterfront town of Fulton is a place where scenic natural beauty, history and heritage, and outdoor recreation meet. Located 100 yards from the river, the Andresen Nature Center is a fun, informative destination for the entire family. The center offers a diverse look at insects, geography, wildlife, flora, and fauna that are unique to the Upper Mississippi River watershed. The Martin House Museum gives visitors a peek into local history within a historic red brick building.

Do not miss a trip to Fulton's authentic Dutch windmill, or a visit to the Windmill Cultural Center, which features a collection of 22 windmills of varying sizes. If you want to camp in the area, set up your tent or RV at the nearby Morrison Rockwood State Park. The expansive park offers a campground as well as fishing and boating opportunities on Lake Carlton.

Wherever your Illinois travel plans take you, these seven picturesque small towns are sure to win you over. So, the next time you find yourself in the Midwest, whether you are on a summer road adventure or a business trip to Chicago or another big regional city, take the time to explore all of the history, culture, natural beauty, and outdoor recreational opportunities that these charming Illinois towns offer. From wide, open prairies to intimate, historic downtowns, you will find it all in this Midwestern state.

  1. Home
  2. Places
  3. Cities
  4. The 7 Most Picturesque Small Towns In Illinois

More in Places