(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)

A perennial favorite.

The 72nd Annual Halloween Window Painting on Purchase Street in downtown Rye on Sunday, October 19, 2025 was well attended by pumpkins, princesses, superheroes and regular Rye families. The day also featured the second annual Halloween costume parade. The day was organized by Rye Recreation and Children’s Philanthropy of Rye with assistance from Rye DPW, Rye PD and local merchants.

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(PHOTO: Parade costume contest winners at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: Parade costume contest winners at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: Dressed up as campaigning politicians: Councilmember Keith Cunningham and mayoral candidate Rick McCabe at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: Dressed up as campaigning politicians: Councilmember Keith Cunningham and mayoral candidate Rick McCabe at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: Dressed up as campaigning politicians: Councilmember and mayoral candidate Josh Nathan, council candidate Marion Anderson and Councilmember Keith Cunningham at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: Dressed up as campaigning politicians: Councilmember and mayoral candidate Josh Nathan, council candidate Marion Anderson and Councilmember Keith Cunningham at the 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)
(PHOTO: The 72nd Annual Halloween Window Painting (and second annual parade) on Purchase Street in Downtown Rye, NY on October 19, 2025.)

Jay Sears is the owner and publisher of MyRye.com. He is a 20+ year Rye resident. Contact MyRye.com: https://myrye.com/tips

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