The CRRR first line opened between Springfield and Northampton in 1845 and by the following summer was extended to Deerfield, Massachusetts, and then to Greenfield in November 1846.

This allowed the CRRR to provide rail service between Springfield, Massachusetts and Brattleboro, Vermont.

For over 40 years, the CRRR operated on its own and acquired a vast network of rail lines north of Brattleboro to Canada.

It became part of the route for crack New York–Montreal trains as early as the 1860s, and was acquired by the Boston and Maine Railroad in 1893.

The Chicopee Falls (1845), Easthampton (1872), and Deerfield (1906) branches were built and served the railroad until two of the three were abandoned by the Guilford Rail System (now Pan Am Railways).