Before redevelopment, a hotel and numerous trolley lines were located on the site. A roadway at one time crossed the site where the Town Hall parking lot is now located. A perfectly straight row of mature trees attests to the alignment of the roadway.

In 1990 Carl Stearns, a landscape architecture student, completed a planting plan for the town, which is in the process of implementing it. In addition, a Town Green Advisory Committee has been charged with guiding the overall development of the green. The Thompsonville Revitalization Strategy, completed in 1992 by a team headed by architects Russel Gibson von Dohlen Inc., proposes brick sidewalks that would bisect the green.

Contemporary uses of the green include political rallies, farmers markets, summer concerts, and a Fourth of July celebration.

The Enfield Green is significant as an example of a town green created in the late 20th century.