1. Dr. W.J. Perry House, 321 E. Main Street. This house was built in 1914-15 for Dr. Perry and now houses the Douglas Gallery (house was restored in 1990). Of note are the tin ceilings. The house was home to the County Department of Social Services from 1952-1978.

2. Chesterfield Baptist Church, corner of E. Main Street. and Craig Street this imposing brick edifice was constructed in 1928.

3. John Craig House, 203 E. Main Street. This home was completed in 1798 by the town's first settler, John Craig. The oldest house in town, it was used by Union General William T. Sherman as his headquarters during his stay in the Civil War.

4. Post Office, corner of E. Main Street and Scotch Rd. The grounds of this building, built in 1937, were once home to an Indian trading post. Inside is a fine example of New Deal Art, a relief sculpture "The Farmer's Letters," The Sculpture is one of only two such sculptures commissioned for post offices in the Palmetto State.

5. 1884 County Courthouse, 100 W. Main Street. This building, with its imposing cupola, was built to replace the previous courthouse which was burned by Sherman's troops during the Civil War. A monument on the grounds marks the site of the first secession meeting held in the South preceding the Civil War.

6. Old County Jail, 100 W. Main Street. This building was built in 1885 as a jail and as a residence for the sheriff. Its steps are made from granite salvaged from the 1825 Courthouse burned in the Civil War.

7. Bank of Chesterfield Building, 108 W. Main Street. Constructed in 1908 near the peak of the town's prosperity following the completion of railroad service, this building is now home to a restaurant. 

8. County Courthouse, 200 W. Main Street. This modern building was completed in 1977 as the center of Chesterfield County Government.

9. Austin-Craig House, 302 W. Main Street. This house was completed in 1858 as a residence for a Mr. Austin, a lawyer from Pennsylvania. According to legend, Union troops attempted to burn the house during the Civil War but stopped when told by a slave woman it was built for a "Yankee". Evidence of the fire remains visible.

10. St. Paul United Methodist Church, 305 W. Main Street. This Gothic Revival church building was completed in 1905.

11. John T. Hurst House, 306 W. Main Street. This Colonial Revival-influenced house was built in 1904 for a local merchant.

12. B.C. Moore House, 312 W. Main Street. This house, currently under renovation, was built in 1914 for the founder of the B.C. Moore department store chain.

13. Dr. Dewitt Thompson Teal House, 508 W. Main Street. This imposing residence was built in 1921 for Dr. Teal. He once supplied electricity to the town.

14. Old Courthouse/School, 601 W. Main Street. This building, now a residence, was constructed as a temporary replacement to the courthouse burned in the Civil War. It was moved to its present location around 1900 and converted into a school.

15. Dr. Thomas E. Lucas House, 716 W. Main Street. This house was built in 1868 for Dr. Lucas, a member of the S.C. House. According to legend, he made the money to build the home while serving as a doctor to Union troops stationed here following the Civil War.

16. Mt. Tabor United Methodist Church, W. Blvd. This church building was completed in 1878. According to legend, a group of freedmen met in a brush arbor before erecting a building. The grounds contain the original church bell.

17. Old Mall, 109 Church Street, This building was completed in 1900 and housed a general merchandise store, hotel, market and bank. It is now an apartment complex.

18. William Duke Craig House, This house, c. 1820, stood on the site of the 1977 Courthouse before being moved here. Craig, who owned the nearby Craig's Grist Mill, donated the land for Craig Park.

19. Craig Park, between Page Street and Park Drive, Completed in 1935 as a WPA project, this park was built on lands donated by William Duke Craig. The park area includes picnic facilities, playground, amphitheater and community house and is especially inviting in spring when dogwood, the town tree, is in bloom.

20. Chesterfield Presbyterian Church, West Main Street Established 1908. The history of the church orginates in 1889 with nine members. In 1894 the church dissolved, but reorganized in 1908 with 15 members.