She is originally from Maplewood, New Jersey, where she attended Columbia High School. Winslow later received a BFA in Acting/Musical Theatre at Carnegie Mellon University. Pamela Winslow was engaged to be married to television talk show host and restaurateur Ken Boxer during the mid 1990s. They met during Pamela Winslow's performance in "Hello Dolly" at the Santa Barbara Civic Light Opera on September 24, 1994.
- Beauty and the Beast, as Babette (Replacement)
- Meet Me in St. Louis (1990), as Lucille (Replacement)
- Into the Woods (1987-1989), as Rapunzel (U/S Cinderella, Florinda, and Lucinda)
- Steal Big Steal Little (1995), as Melanie
- Little Sister (1992), as The Girl
- Passionata (1992), as Liana Buckman
- Into the Woods (1991), as Rapunzel
- Star Trek: The Next Generation
- They Came from Outer Space
- Cindy in "Look Who's Barking"