Woolsey may refer to:
In places:
- Woolsey, Georgia, USA, a town
- Woolsey Flat, California, USA, a former settlement
In people:
- Calvin Woolsey, American physician and pianist
- Kit Woolsey, bridge expert
- Lynn Woolsey, American politician
- Matt Woolsey, American writer
- Melancthon Taylor Woolsey, United States Naval officer
- R. James Woolsey, former Director of the CIA under the Bill Clinton administration
- Robert Woolsey, American film comedian
- Ted Woolsey, American video game translator
- Theodore Dwight Woolsey, past president of Yale University
In fictional characters:
- Richard Woolsey, a character in Stargate SG-1 and Stargate Atlantis
In other uses:
- USS Woolsey, two ships in the United States Navy
- Woolsey (convention), a Bridge convention