Montgomery, Massachusetts, first settled by European colonists around the 1760s and incorporated in 1780, has always been one of Hampden County’s smallest towns. Named after General Richard Montgomery, who died in the Battle of Quebec, its early development was primarily a collection of scattered farms rather than a concentrated village. While a “town center” emerged with the construction of a meeting house and later a town hall and churches in the mid-19th century, it was never a bustling hub. The town’s population fluctuated significantly, reaching a peak of around 740 by 1840 before declining steadily for a century, hitting a low of just 141 residents in 1930. Its history reflects the challenges faced by many small, rural New England communities without significant industrial development or major transportation routes.

Today, Montgomery, Massachusetts, remains a quiet, rural residential community nestled in the Berkshire foothills, with a population of approximately 819 as of the 2020 census. While its industrial past was minimal, the town’s charming historic center, with its Greek Revival-style buildings, is well-preserved and now houses the town hall, library, and historical society. The landscape is more forested than in past centuries, contributing to its scenic appeal. While it serves as an outer commuter town to Springfield, Montgomery maintains its peaceful character and is known for its natural beauty, including the Westfield Reservoir and Tekoa Reservoir. The town’s commitment to preserving its historical buildings and rural ambiance continues to define its present-day identity.