Massachusetts Avenue may refer to:
- Massachusetts Avenue (metropolitan Boston), Massachusetts
- Massachusetts Avenue (MBTA Orange Line station), a subway station on the MBTA Orange Line
- Massachusetts Avenue (MBTA Silver Line station), a station on the MBTA Silver Line Washington Street route
- "Massachusetts Avenue", a song by Amanda Palmer & the Grand Theft Orchestra from the 2012 album Theatre Is Evil
- Massachusetts Avenue (Halifax, NS)
- Massachusetts Avenue, Indianapolis, Indiana
- Massachusetts Avenue (San Diego Trolley station), a station on the San Diego Metropolitan Transit System
- Massachusetts Avenue (Washington, D.C.), the longest of the state named streets in Washington, D.C.
- Massachusetts Avenue Historic District (Worcester, Massachusetts)
- Massachusetts Avenue, a street in the game Monopoly