The Columbia Greenway Rail Trail is Westfield’s Rail Trail. The Rail Trail is a multi-modal linear park, which follows along a portion of the route of the former New York / New Haven / Hartford Rail Road (and one-time Northampton, Massachusetts to New Haven, Connecticut canal). Stretching from Southwick, Massachusetts to the south, to the Great (Westfield) River Bridge to the north, the Columbia Greenway Rail Trail traverses downtown Westfield on a mostly elevated line for a total of 3.2 miles. The first section from Southwick to just south of Tin Bridge was completed as of Fall 2012.

The Rail Trail incorporates bridge crossings of all streets in the downtown, with one surface street crossing at Shaker Road. The Trail will tie into the Southwick trail to the south and then become the Farmington Valley Greenway, extending to New Haven, Connecticut. At a future date, the Columbia Greenway Rail Trail will extend northward from the Westfield River, eventually connecting to communities in Southampton, Easthampton (the Manhan Rail Trail) and Northampton (the Norwottuck Rail Trail).