Chester was settled in the 1760s, with early settlers of the North Chester area including members of the Elder, Smith, and Mann families. One of the most substantial buildings, known as the Cushman Tavern, stands at the junction of East River, North Chester, and Smith Roads; it was built by Thomas Elder about 1773, and served stagecoach travelers on the River Road, which was the preferred route between Springfield and Pittsfield. A short way north of the Smith Road bridge are the remains of a breached dam, where the first sawmill and gristmill stood, built by John Stevens. The large well built up on the building is impressive!

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