The tunnel project was originally proposed in 1819 as a canal to connect Boston to Upstate New York via the Deerfield River on the east of the Hoosac Range and the Hoosic River on the west. That project was shelved, and later reborn as part of the new Troy and Greenfield Railroad. The project was nicknamed The Great Bore by its critics, including future Supreme Court Justice Oliver Wendell Holmes, Jr., who said that he would like to wall up a dozen lawyers at one end of the tunnel and put a good fee at the other.