For the third time in as many years, drivers in the 1906 Vanderbilt Cup Race faced a new course layout. The construction of a new trolley line stretching from Queens to Mineola forced a redesign of the western section of the course from its 1905 configuration. The grandstand returned to its 1904 site on Jericho Turnpike in Westbury. The first 12 miles of the new 29.7-mile course was unaltered from 1905, including the turns at Jericho, East Norwich, and Bull’s Head Hotel in Greenvale. The remaining 17.7 miles presented hilly sections and more challenging turns than drivers had seen before. After heading south on Glen Cove Road, the revised course included a “Hairpin Turn” in Old Westbury, two new turns in Roslyn, the challenging hills in Manhasset Valley, and two more turns in Lakeville. The final challenges were a turn at Krug’s Hotel in Mineola and a nearby railroad crossing heading back east on Jericho Turnpike. In all, the course presented 11 turns per lap or a total of 110 during the 10-lap, 297-mile race.