While playing for Boston, Bennett returned each year to his home in Detroit for the off-season, and also traveled with his dog to Williamsburg, Kansas, for extended hunting trips. In 1894, Bennett was joined on his annual hunting trip by pitcher John Clarkson. On January 10, 1894, Bennett's legs were crushed by a Santa Fe Railroad passenger train in Wellsville, Kansas, while traveling from Kansas City to Williamsburg.
