[1] Alford was first settled in 1756 as part of a land purchase from the Shauanum Stockbridge Mahican tribe by a group led by Timothy Woodbridge.

The town, originally part of Great Barrington, separated in 1769 and was officially incorporated in 1773.

It was named for Colonel John Alford of Charlestown, who was known for preaching Christianity to Native Americans and for sponsoring a theology professorship at Harvard College's Divinity School.

This would come to an end when the railroad was laid in a neighboring valley, rendering the last operating quarries of Alford unable to compete.

Around New Year's Day, 1776, General Henry Knox passed into Massachusetts through the town, bringing cannons from Fort Ticonderoga eastward to help end the Siege of Boston.

Today, this route is known as the Knox Trail, and a marker is located at the state line.

The Knox Trail follows this route into the state, and the road heads southeastward into Egremont before ending in Great Barrington.

The population density was 34.5 inhabitants per square mile (13.3/km2), which ranks 21st in the county and 326th in the Commonwealth.

Alford uses the open town meeting form of government, and is led by a board of selectmen.

On the state level, Alford is represented in the Massachusetts House of Representatives by the Fourth Berkshire district, which covers southern Berkshire County, as well as the westernmost towns in Hampden County.

[16] The town is patrolled by the First (Lee) Station of Barracks "B" of the Massachusetts State Police.