[3] The area that is today described as Westford, Vermont originally fell within the traditional territories of the Sokoki, Missisquoi, and Cowasuck bands of the Western Abenaki tribes.

Newly introduced infectious diseases and attacks by English settlers greatly impacted native populations and prompted their emigration to Quebec by the 1670s, opening the land for settlement by European immigrants.

New York immediately began redistricting the area by land patent, putting Westford within the now-extinct Charlotte County (formed 1772), and requiring residents to repurchase their land from New York in order to retain legal title.

In response New York declared that it would halt further subdivision of settled areas until clarification of King George III's intent was made clear.

In her bicentennial work, Vermont Place-Names, historian Esther Munroe Swift suggests that some of the more abstract names of Westford's hills may closely reflect the sentiments of the original English settlers.

Smaller communities include the hamlet of Cloverdale (located near Vermont Route 15 in Westford's northeast corner), Osgood Hill where early settler Manassah Osgood first settled, Bowman's Corners just south of Brookside, and the historic communities along the northern border with Fairfax, which developed in response to the early industry along the Lamoille River from Fairfax Falls to what is now Fairfax village where the Mill Brook forge was located.

The town's first industrial center was located in the Village of Brookside, an area bounded on three sides by the Rogers Brook.

Other businesses flourished along the northern town line with Fairfax, where the Mill Brook forge worked iron ore mined in Colchester from 1796 until its closure in 1810, and in the Hamlet of Cloverdale which developed surrounding the Cloverdale Creamery and freight station on the Burlington and Lamoille Railroad running between Burlington and Cambridge.

Professional services, agribusinesses, transportation and construction companies make up the greatest number of commercial concerns.