Many engineers claimed that the grade would be too steep and the railroad could not be run. A Mr. Jarvis whose experience included the Erie Railroad and Croton Aqueduct, said that it could be done with good equipment. The first 8 miles above Bennington had a maximum grade of about 4.35% (230 feet in a mile). Some branches had a maximum grade of about 4.73% (250 feet in a mile). The line was constructed using 36 pound rail to a gauge of 4 foot 8 inches, standard gauge is 4 foot 8 and a half inches.
The railroad followed Walloomsac brook valley as most of the company's timber tracts were in this valley between 1,200 and 1,500 feet above sea level. From April 1872 to November 1872 Morrison & Bering's Swedish work crews worked when the weather permitted, about 15 days per month on average. In October the first trains began to run. In 1873 The line bought a 4-4-0 from the Housatonic Railroad. It was retired in 1875, when a lighter Rogers 4-4-0 was purchased, from Shepaug, Litchfield & Northern R.R. This Rogers steam engine was sold to the Bennington & Rutland R.R. where it retained its original number, 3, after the Bennington & Glastenbury Railroad shut down, in March of 1889.
The Bennington & Glastenbury Railroad, Mining and Manufacturing Company's main sawmill could produce 1,000 board feet of lumber per hour. They operated up to eighteen 1,600 bushel charcoal kilns. In 1888 most of company's accessible timber had been cut. In 1888 a blizzard shut down the line for about 3 months. March 1889, operations on the B.&G.R.R. stopped. In 1890 the company's mortgage was foreclosed.
The Bennington and Woodford bought, three second-hand, open single truck trolley cars from Saratoga. There were plans to acquire some new large 45 foot double truck, interurbans, after a successful first season. The company did not get any new equipment, they did however acquire a fourth single truck open trolley and a trailer (second hand). The article on the B&W electric railway stated that some one remembered the company operating an unusual 2 truck trolley for a while, although there were no written records to that effect. The unusual trolley was said to have been made by combining two single truck cars.
According to O.R.Cummings, in the C.R.E.R.A. publication on the Berkshire System, the unusual car was made by the Bennington & Hoosack Valley, rather than the Bennington and Woodford. This trolley was made from a combination of two single truck powered trolleys and/or two trolley trailers.
The first year was a great success, mostly because of advertising and publicity in affluent sections of New York State. On October 6th, 1895 the Bennington & Woodford's first season came to a close. October 12th a special excursion was run for some folks from Bellows Falls.
In 1896 the Casino and a theater were opened and the line was extended to a mill that was converted into an dance hall, with bowling alley, a hotel across from the entertainment hall was reopened as "The Glastenbury Inn".
On October, 5th 1898 a torrential down pour caused flooding and the 1st few of miles of trolley roadbed north from North Bennington were washed down stream. The company never rebuilt.
Bennington Electric Railway's successor, The Bennington and Hoosac Valley Street Railway, acquired their equipment and eventually constructed a trolley route from Bennington to North Bennington. It is interesting to note that the construction of this extension was not done until after the fall of the Bennington & Woodford Electric Railway, even though it was Bennington Electric Railway officials who blocked the expansion of B & W electric railway from North Bennington to Bennington, at a public town meeting a few years before the wash out occurred.
Transportation , A publication of the Connecticut Valley Chapter of the National Railway Historical Society, Vol. 6 part 2 May 1952, Bennington & Glastenbury Railroad Bennington & Woodford Electric Railway, by Donald E. Shaw.
Transportation Bulletin, A publication of the Connecticut Valley Chapter of the National Railway Historical Society, Vol. 72 January-December 1972, Berkshire Street Railway, by Cummings, O.R..