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Answer:
DERBY
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You can bet on it
Churchill Downs event
Bowler
Felt hat
Rounded felt hat
Kentucky attraction
Horse race
Epsom Downs event
Bowler's cousin
Hat type
Louisville race
Hat or race
Game on skates
Chaplin chapeau
Bean covering
Annual May event
Annual Kentucky horse race
Triple-Crown unit
Track thriller
Stiff hat with a rounded top
Stan Laurel trademark
Rounded topper
Roller or demolition follower
Roller ___
Roller __
New Brunswick community or English namesake
Narrow-brimmed hat
Londoner's "billycock"
Kentucky has a famous one
Kentucky event
Hemispherical hat
Headgear for Hardy
Hat with a rounded crown
Hat or contest
Hardy's headgear
Competition for three-year-olds
Competition for 3-year-olds
Charlie Chaplin's hat
Chaplin's chapeau
Bowler hat
Annual Kentucky event
Annual event in Louisville