It was felt from the beginning that a work of such magnitude must have the aid of machinery for its execution. Accordingly, a huge machine was built, weighing seventy-five tons, and in the year 1852 was brought face to face with the mountain which it was expected to subdue. It was designed to cut a groove about a foot in width, awl corresponding with the circumference of the proposed tunnel. When this groove bad been cut to a sufficient depth, the machine was to be drawn back, and the great core of rock left in the centre was to be blasted out with powder, or broken off with wedges. When the broken rock had been removed, the operation was to be repeated. The machine promised well. It actually penetrated the mountain to a depth of ten feet., but then it became hopelessly disabled, and gave evidence that it was not adequate for the work to be done. It was sold subsequently for old iron. Two years now passed without any progress in the work. Meantime the aid of the State had been earnestly sought. The legislature had been applied to in 1851, for a loan of $2,000,000. The application was unsuccessful. Another, two years afterward; was also denied, though in both cases committees had reported favorably. Finally, in 1854, the State having consented to give the desired aid, a contract was entered into with E. W. Serrell & Co., under which some work was done. The conditions of the loan were that $600,000 should be subscribed to the stock of the company, and twenty percent of it paid in. Then for every seven miles of road and one thousand linear feet of tunnel completed the company were to receive $100,000 of state scrip. These conditions were found to be difficult of fulfillment, and the work advanced slowly. In the same year that the loan was obtained, the legislature authorized the towns adjacent to the road to aid it to the extent of three percent of their valuation. But in two years only five hundred and twenty shares were taken, and all the money received on them was $1400 from the town of Adams. The contract with Serrell & Co. having thus practically failed, a new contract was entered into with H. Haupt & Co., the next year, to complete the road, with the tunnel, for the sum of $3,880,000, which soon after, by another contract, was increased to $4,000,000. The work now went on without serious interruption. The contractors were energetic and sanguine. Mr. Haupt revived the project of using machinery, and at an expense of 825,000 had another boring engine constructed, which he was very confident would prove successful. He wrote to General Wool concerning it in 1858: “The slowest progress of the machine when working will be fifteen inches per hour; the fastest, twenty-four inches. A machine at each cod, working but half the time with the slowest speed, should go through the mountain in twenty-six months.” This machine never penetrated the mountain an inch, and the work was continued by manual labor, as before. In the latter part of the year 1858 the work had progressed so far that the contractors were able to draw the first installment, $100,000, of the state loan. In 1860, subscriptions to the road still failing, on account of the unwillingness of capitalists to engage in a work attended with so many difficulties and uncertainties, the legislature authorized the application of $650,000 of the state loan to the building of that part of the road situated east of the tunnel, the payments to be in monthly installments.

The progress of the work now scented assured. But in 1861, owing to a misunderstanding between the contractors and the state engineer in regard to the payment of the installments of the loan, Haupt & Co. gave up their contract, and the work was again stopped.