Macoupin County Jail

The historic 1869 Macoupin County Jail was designed by E.E. Meyers. It was built using the "cannon ball" method which prevented jail breaks by making it nearly impossible to remove the blocks. This unique medieval-inspired fortress housed many lawbreakers during its 119 years of use, but only one prisoner escaped. He was soon apprehended a few blocks from the jail.

CITY: Carlinville

Fulkerson Mansion and Farm Museum

Colonel William H. Fulkerson's mansion and farm museum contains many rare agricultural items and equipment with emphasis on large, rare farm steam traction engines, utilized for plowing the prairie, threshing the grain, and for powering early sawmills. The estate is 14-room Southern-style Victorian mansion that has remained virtually unchanged to this day. It was placed on the National Historic Register of Historic Places in 1998.

CITY: Jerseyville

Macoupin County Historical Society Museum

The Macoupin County Historical Society Museum is housed in the John Anderson mansion, originally built in 1883. The main house is a museum with exhibits that chronicle the development of Macoupin County and its citizens. In addition to the mansion, several other buildings on the grounds emphasize the county's history: a one-room schoolhouse, blacksmith shop, church, wash house, granary and herb garden.

CITY: Carlinville

Carlinville Historic District

The Historic District includes the Macoupin County Jail, Million Dollar Courthouse, and the largest collection of Sears & Roebuck mail-order homes in the U.S.

CITY: Carlinville

Historic Wabash Train Depot

This historic train depot features a preserved facade and a renovated interior that houses specialty shops.

CITY: Litchfield

Macoupin County Courthouse

The Macoupin County Courthouse, built in 1870, used to be the largest county courthouse in the United States, with the possible exception of one in New York City. It was even larger than the Illinois Statehouse. While the courthouse still serves as the seat of county government, it has also become a showplace that attracts tourists, architects and artists from across the country, as well as overseas.

CITY: Carlinville

Porthole Barn Trail

After the Civil War, Confederate shipbuilder Joe Minch was looking for a fresh start. He made his way back to the Rockbridge area and traded his building expertise for a set of tools. That first project of building a barn set into motion a new trend in barn design. Joe placed round windows, now know as portholes, in the barn. Travel through Greene County today to view the highest concentration of Porthole Barns in the country.

CITY: Carrollton