The Pilgrim Man and Woman Balloonheads are part of the start of the Macy's Thanksgiving Day Parade. The original pair began appearing in 1975 and appeared up until 1997. A new pair was introduced in 2005, which are always behind the Tom Turkey float.
- In 1997, The Pilgrim Man's hat was accidentally detached duing preparation,
- In 2018, the Pilgrim Man Balloonhead was taken out of the route at Central Park South due to unknown circumstances. Additionally, the Pilgrim Woman Balloonhead left the parade route at Herald Square while Sugarland was performing.
- In 2019, the Balloonheads couldn't appear at all due to strong wind gusts.