Created in 1943, the Hillsboro Branch extended originally to its namesake town, Hillsborough. This was eventually cut back to Bennington in 1979. When the Boston & Maine Railroad was purchased by Guilford Transportation Industries in 1983, they continued to serve the paper mill in Bennington, but a labor strike on the railroad prompted the mill to convert to trucks. After the conversion, no customers remained past Wilton and Guilford had no reason to keep the line open. The State of New Hampshire purchased the Hillsboro Branch from Howard Street in Wilton to the end of the line in Bennington to preserve the line for future rail use.
In 1992, the Milford-Bennington Railroad (reporting mark MBRX) started operation moving stone for Granite State Concrete Co. between its quarry in northern Wilton to its processing plant on the west side of Milford. Milford-Bennington holds a touch of the past as it continually uses a caboose on its trains, however not as its traditional role as an office. Because there's no run-around sidings at either facility, the stone train backs up the hill to the quarry in Wilton, so the caboose is used by crew members as the eyes and ears for the engineer at the back of the train.
Through the years, the relationship between Guilford Rail System, and later Pan Am Railways, and the Milford-Bennington has been one full of tension. In 2010, Pan Am Railways refused to allow Milford-Bennington to exercise its trackage rights between Wilton and Milford due to issues stemming from a grade crossing accident the prior year that was determined to be not the fault of the railroad. The Milford-Bennington Railroad did not run a single trip in 2010 forcing Granite State to truck in its stone from alternative sources to its Milford processing plant. Since resuming operation in late 2011, Milford-Bennington and Pan Am Railways have continued to have a strenuous relationship.
In 2003, passenger service returned to the region with the start-up of the Wilton Scenic Railroad, which traveled between Wilton and Greenfield. The scenic train ran weekends and select days during the week depending on the season using two Budd RDCs originally from BC Rail in western Canada.
The train departed from downtown Wilton in the shadows of the old Wilton Station behind the Wilton post office and allowed visitors to witness the beauty of the Monadnock region, especially during the fall. Briefly the scenic train stopped in the center of Greenfield until track work and trimming were completed to the state park. By mid-summer the railroad reached Greenfield State Park, which back in the 1800s was also a stop for trains that brought people from around the region to the fair at what is today Oak Park. In the last year of its operation, the Wilton Scenic's journey was extended out to Spring Pond Farm at Muzzy Hill Road where visitors aboard the train could admire the alpacas at the farm.
Unfortunately the owner passed away prior to the 2006 season and scenic train rides were not continued. The two Budd cars were eventually sold and moved down to Newport, Rhode Island in 2007. They are owned and operated by the Newport Dinner Train and are used for the Islander Touring Train. If you're down in the Newport area, take a ride on these cars and enjoy the views of the Naragansett Bay.
- In Memory of Stuart Draper (1938-2006) -