Pumpkin Roll
When and Where
One of Brookville’s favorite fall traditions! After Halloween, families gather to send their pumpkins rolling down the steep hill of Pickering Street (known as Shanghai to the locals) in a race of laughter, cheers, and pumpkin pieces.
The event is organized by PATHS (Parents and Teachers Helping Students) with help from the Brookville Fire Department. When the last pumpkin crosses the finish line, everyone pitches in to gather the remains, which are donated to a local farm.
It’s simple, it’s mess, and it’s pure small-town fun! The kind of memory that sticks with you long after the pumpkins are gone.
Meet at the corner of Pickering and Church Streets. Divided into age groups, races begin shortly after.



