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. The town has been mostly agricultural throughout its existence, although several small mills and a marble quarry existed in the nineteenth century.

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.

According to the United States Census Bureau, the town has a total area of 11.5 square miles (29.9 km²), of which 11.5 square miles (29.8 km²) is land and 0.04 square miles (0.1 km²), or 0.35%, is water. Alford lies along the western border of Berkshire County and Massachusetts, east of Columbia County, New York. The town, which is roughly shaped like an arrowhead, is bordered by to the northeast, Great Barrington to the southeast, Egremont to the south, and Hillsdale and Austerlitz, New York, to the west. Alford is located 19 miles (31 km) south-southwest of Pittsfield, 50 miles (80 km) west-northwest of Springfield, 138 miles (222 km) west of Boston, and 44 miles (71 km) southeast of Albany, New York.

...
Wikipedia