Vandiver started a lumber business in Havre de Grace in 1865. He remained there until 1878. He then joined his father in the business of shipping brick moulding sand. His father died in 1885 and he ran the business until 1890.[1][4]
Vandiver was a Democrat. He served in the Maryland House of Delegates in 1876, 1878, 1880, and 1892. In 1881, he was defeated by Herman Stump. He was one of the signers of the charter of Havre de Grace and served as mayor from 1885 to 1886. In 1892, he served as Speaker of the Maryland House of Delegates. In 1892, he was appointed a commissioner for the World's Columbian Exposition. In June 1893, President Grover Cleveland appointed him Collector of Internal Revenue for Maryland, the District of Columbia, Delaware and Virginia's Eastern Shore. He served in this role from July 1, 1893, to 1897.[1][4] He was a delegate to the 1892, 1896, 1900 and 1904 Democratic National Conventions.[1][2] He served as chairman of the Democratic State Central Committee from August 12, 1897, until his death. He served as secretary and treasurer of the committee from 1887 to 1892.[2][4][5]
Vandiver was the director of the First National Bank of Havre de Grace, Commonwealth Bank of Baltimore, Commonwealth Savings Bank, American Banking and Trust Company of Baltimore, Third National Bank of Baltimore, National Bank of Port Deposit and the Delaware Railroad. He also served as director for philanthropic organizations in Havre de Grace, including the Harford Agricultural Society, Maryland Agricultural College, Havre de Grace Improvement Company and the Havre de Grace Water Company. He was trustee of the Maryland Agricultural College.[1][4]
Vandiver bought land from Havre de Grace mayor J. Thompson Frieze. In 1886, he built a Queen Anne style house in Havre de Grace, Maryland, at 301 South Union Avenue that would be called the "Vandiver Mansion".[3][7]
Vandiver received silver service after his election to treasurer in 1900. The items were commissioned by the Democratic Party and manufactured by Samuel Kirk & Son Co. of Baltimore. The articles are in the possession of the Maryland State Art Collection.[8]
The Vandiver mansion at 301 South Union Avenue in Havre de Grace was converted into the Vandiver Inn in September 1987. The property is now used as a bed and breakfast.[9]