Welcome to Montgomery, Massachusetts. We are a rural, residential town situated in the Berkshire foothills. Montgomery's land area is about 15 square miles. First settled in 1767, and incorporated in 1780, Montgomery was until fairly recently a farming community. Our Geography. Montgomery is bordered by Tekoa Mountain to the south, which overlooks the Westfield River Gorge and the Connecticut River Valley. The Tekoa Mountain region was originally inhabited by Native Americans of the Woronoake tribe.