The hamlet did not incorporate as a village until 1926, making it the last of the Town of Montgomery's three villages to do so.

Maybrook's development as a village owes much to the railroads, and in 1910 the largest rail hub in the East was built there. It stayed open until 1974, employing 1,500 at its peak.

Today the railroads are gone but the village's proximity to Interstate 84, the New York State Thruway and Stewart International Airport ensure its continued status as a transportation and distribution center. Yellow Freight operates a center in the village and is its largest employer. For many years, Maybrook was a local destination for Pat's Pizza, Four Star Video, and Lu-Jon's Ice Cream.