The Highwaymen is the name of at least two musical groups:
- A circa 1960 "collegiate folk" group, which originated at Wesleyan University and had a hit in 1961 with "Michael Row the Boat Ashore". They have played reunion gigs as recently as 2002.
- A country supergroup of outlaw country musicians Willie Nelson, Waylon Jennings, Johnny Cash, and Kris Kristofferson, famous for their song "The Highwayman."