Chesterfield IllinoisATTRACTIONS & THINGS TO DO


Listed below are the best attractions and things to do near Chesterfield, Illinois.



1. Wild Pickins Winery

SCENIC COUNTRY VINEYARD


Wild Pickins Winery is a charming winery set amidst rural woodlands, offering a tranquil setting perfect for wine lovers and casual visitors alike. Guests can sample a range of locally crafted wines while enjoying views of the picturesque vineyard. The welcoming atmosphere and beautiful surroundings make this spot a favorite for gatherings and relaxing afternoons.


2. Beaver Dam State Park

RECREATIONAL OUTDOOR HAVEN


Beaver Dam State Park spans over 750 acres and features a scenic lake, hiking trails, and opportunities for boating, fishing, and picnicking. The park's wooded terrain is perfect for nature walks, birdwatching, and observing the changing seasons. With campgrounds and picnic areas, it provides a peaceful retreat just a short drive from Chesterfield.


3. Carlinville Historic Square

CHARMING DOWNTOWN DISTRICT


Carlinville Historic Square is known for its well-preserved 19th-century architecture and vibrant mix of shops, restaurants, and historic sites. Visitors can stroll the brick-lined sidewalks and visit unique boutiques, antique stores, and inviting cafes. The courthouse and neighboring buildings capture the small-town charm and history of Macoupin County.


4. Anderson Mansion Museum

VICTORIAN-ERA HOUSE MUSEUM


The Anderson Mansion Museum offers a glimpse into Carlinville's storied past with its beautifully restored rooms and original furnishings from the late 1800s. Guided tours highlight the unique architectural features and the stories of the families who lived there. The museum serves as a window into local history and Victorian-era life in central Illinois.


5. Standard Addition Historic District

SEARS ROEBUCK KIT HOMES


The Standard Addition Historic District is famous for its collection of Sears Roebuck kit homes built in the early 20th century for Standard Oil workers. Visitors can walk or drive through the neighborhood to see dozens of well-maintained, catalog-built houses. The district tells the fascinating story of early prefabricated architecture and community planning.



6. Macoupin County Courthouse

ARCHITECTURAL LANDMARK


Standing at the heart of Carlinville, the Macoupin County Courthouse is an impressive example of 19th-century public architecture with its grand clock tower and stately columns. Visitors admire its scale and learn about its unique history, sometimes referred to as the "Million Dollar Courthouse" for its notable construction cost. The courthouse remains a focal point for community events and local history.


7. Gillespie Area Historical Museum

LOCAL HERITAGE EXHIBITS


The Gillespie Area Historical Museum showcases artifacts, photographs, and displays that chronicle the people and events that shaped the Gillespie region. Housed in a historic building, its collections include mining equipment and memorabilia from the area's coal mining era. The museum is a valuable source of local history and community pride.


8. Lake Lou Yaeger

WATERFRONT RECREATION SPOT


Lake Lou Yaeger is a popular destination for boating, fishing, swimming, and camping near Litchfield. The lake is surrounded by a mix of forest and open space, providing scenic trails for hiking and areas for wildlife observation. Its sandy beach and marina facilities attract visitors throughout the warm months for outdoor fun.


9. Ariston Café

HISTORIC ROUTE 66 DINER


Opened in 1924, the Ariston Café is one of the oldest continually operating restaurants on historic Route 66. Travelers stop in to enjoy its classic American fare and vintage diner atmosphere, which has been carefully preserved. The café is a beloved stop for Route 66 enthusiasts and fans of traditional roadside Americana.


10. Litchfield Museum & Route 66 Welcome Center

ROADSIDE HISTORY HUB


The Litchfield Museum & Route 66 Welcome Center invites visitors to explore the fascinating history of Route 66 and the Litchfield area. Exhibits include vintage automobiles, memorabilia, and photographs that capture the spirit of the Mother Road. The center serves as both an educational stop and a photo opportunity for travelers.



11. 39th Illinois Park

CIVIL WAR MEMORIAL PARK


39th Illinois Park is a small but significant green space dedicated to the 39th Illinois Regiment's role in the Civil War. Visitors can walk a short natural trail and read interpretive signs about the regiment's history and local battles. The tranquil park offers a place for quiet reflection and historical appreciation.


12. Wilson Park

COMMUNITY GATHERING PLACE


Wilson Park is a sprawling recreation area featuring playgrounds, walking paths, sports fields, and picnic areas. The park hosts seasonal festivals and community events, making it a lively spot for families and residents. Its well-kept grounds and central location make it a favorite destination in Granite City.


13. Cahokia Mounds State Historic Site

PRE-COLUMBIAN NATIVE SITE


Cahokia Mounds State Historic Site preserves the remains of the largest pre-Columbian city north of Mexico. Visitors can explore ancient earthen mounds, hike interpretive trails, and learn about Mississippian culture in the impressive visitor center. The site is a UNESCO World Heritage Site and an essential destination for history enthusiasts.


14. Mother Jones Monument

LABOR HISTORY LANDMARK


The Mother Jones Monument honors the famed labor activist Mary Harris "Mother" Jones, who is buried in the Union Miners Cemetery. The monument attracts visitors interested in labor history and the early 20th-century labor movements. Interpretive signage and the peaceful setting make it a site for education and reflection.


15. Crossroads Regional Park

SPORTS AND RECREATION HUB


Crossroads Regional Park is a comprehensive recreation facility featuring ball fields, walking trails, playgrounds, and picnic shelters. It's a popular venue for local sports leagues, tournaments, and family gatherings. The park's size and amenities make it a focal point for outdoor activities in Vandalia.