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He also served as an executive with the American Woolen Company, Lehigh Coal and Navigation Company, Waltham Watch Company, Fanny Farmer, Boston Edison Company, Bangor and Aroostook Railroad, Pittsburg and Shawmut Railroad, Boston and Maine Railroad, Boston Garden-Arena Corporation, and Springfield and Eastern Street Railway.
The first company was incorporated in 1846 and opened a line from Newburyport on the Eastern to Georgetown in 1849, and west to the Boston and Maine Railroad at Bradford in 1851.
Interchange was with the Boston and Maine Railroad and the New York, New Haven and Hartford Railroad at the south end of the line at the Buckland station, which is on the opposite side of the Deerfield River from the village of Shelburne Falls.
As profits from the American shipping industry began to wane, he sold his fleet and turned to urban real estate and railroads, in particular the Boston and Albany and Boston and Maine lines.
The Portland Company built early railway locomotives and the Portland Terminal Company handled joint switching operations for the Maine Central Railroad and Boston and Maine Railroad.