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2018 Route 66
          Miles of Possibility Conference

About Carlinville & Macoupin County, Illinois

The history of Carlinville includes many current landmarks and architectural features that stand today as hallmarks of eras gone by, yet still provide insights for discovery and learning.
Macoupin, the county’s namesake, was a favorite food source for local Indians, which matches old accounts that this area was wetland, with natural lakes, and vast amounts of growing macoupin.

Slabbed 2 Lane
Before there was Route 66, Illinois Route 4 was the fully paved, “slabbed” two-lane Mother Road between Chicago and St. Louis. U.S. Route 66 used Route 4 from 1926 until 1930, which ran directly through Carlinville, providing a symbol of freedom, restlessness, and the quest for new opportunity, Historic Route 66.

Carlinville Square
As we explore the many opportunities for discovery throughout Carlinville, our journey begins with the Picturesque Town Square with buildings dating back to the early 1800s.  Carlinville’s Historic Square is the crown jewel of the large historic district that has been on the National Register of Historic Places in Illinois since 1976.  Dine and shop where Lincoln once walked, with brick-paved streets and Victorian cast-iron storefronts.  It is the only Town Square on Illinois Route 66 that went completely around, and today provides access to two major state highways.

Anderson Mansion
In 1973 the Macoupin County Historical Society purchased the Anderson Mansion for use as the Society’s museum.  Annual festivals in May and September feature tours of the museum as well as arts, crafts, collectibles, entertainment, and home cooked foods. Both festivals include displays by the Antique Agricultural Association with antique farming equipment and demonstrations of old farming methods that include threshing. Group tours of the museum and grounds are available by reservation; contact the Macoupin County Historical Society, 920 W Breckenridge Street, Carlinville, IL at (217) 854-2850. 

Million Dollar Courthouse
Designed in 1867, the Macoupin County “Million Dollar” Courthouse began as a $50,000 project supported by bonds and taxes, that through a series of political and social scandals construction was halted when the cost grew to $1.3 million. The Renaissance Revival masterpiece boasts an exterior constructed from gold-colored blocks of stone and a portico with 40-foot Corinthian columns. Inside you’ll find elaborate woodwork, including finely carved walnut seating; a judge bench of Italian marble; and ornately decorated rooms with arched doorways. Abraham Lincoln occasionally practiced law in Macoupin County (although it was at the current courthouse’s less glamorous predecessor). Court documents with his signature are on display in the courthouse.

Macoupin County Jail
Macoupin County Jail, in service from 1869 to 1988, is a Gothic Revival stone structure that has leftover Civil War cannonballs embedded within the walls to prevent jail breaks.  There is a local tale of a man who shimmed through the very narrow slit windows to escape.

Sears Homes
The Standard Addition/Sears and Roebuck Mail Order Houses include the largest U.S. collection of 156 mail order homes.  Built in 1918 for the mineworkers of the Standard Oil Company, the homes represent a lovely trip back in time, yet the homes, were surprisingly modern in their construction and design.

Historical Marker
Historical Marker - This large stone commemorates the spot where Abraham Lincoln delivered a speech on August 31, 1858, when he ran against Stephen A. Douglas for U.S. Senate. Visitors can find the stone in front of the United Methodist Church at the corner of South Broad and East First South Streets.

Guided tours of the historic courthouse, Sears Homes and Step-On Bus Tours are available by contacting the Carlinville Chamber of Commerce Tourism Committee at (217) 854-2141 or email at

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2018 Route 66 Miles of Possibility Conference | October 25-28, 2018 | Blackburn College | Carlinville, Illinois
Contact Carlinville Tourism Director Deb Young at for Carlinville Tours and local info and/or call Great Rivers & Routes Tourism Bureau at 1-800-258-6645 for more information.


©2018 Route 66 Miles of Possibility Conference.