[1] Gregory was a member of the guard of honor to receive General Marquis de La Fayette on his visit to the United States in 1824.

He served three terms on the Hudson County Board of Chosen Freeholders, and was at one time a director of sixteen different railroads.

Upon returning to private business, Gregory was one of the incorporators of the "Mutual Benefit Life and Insurance Company of the County of Hudson" along with several partners including his last predecessor as mayor of Jersey City, Samuel Wescott.

[3] An original stockholder of the Adirondack Iron and Steel Works in Jersey City, Gregory bought the company in 1863.

At the time of his death, Dudley's estate was estimated to be worth $1 million and his will provided for annual payments to be made to some of his children and grandchildren, sister-in-law, and "Adam Thompson, a colored servant.