 In 1795 , Jones surveyed Ancaster , Thorold , Grantham , Beverley , Southwold , Whitby , York , Scarboro , Pickering , the lands of Joseph Brant and Lake Simcoe . On December 24 , 1795 Jones was directed by Lieutenant Governor John Graves Simcoe to survey and open a cart road from the newly planned settlement of York , Upper Canada to Lake Simcoe . Jones began the planning work the next day . On the 29th of that December , Jones was given the assistance of thirty of the Queen 's Rangers for the road 's construction . The work began January 4 , 1796 on this road , which would become Yonge Street . Jones worked as the effective master builder in addition to his title as surveyor . The road reached Holland Landing on February 16 , 1796 , and Jones returned to York on February 20 to inform the Lieutenant Governor that the road was completed . This first incarnation of Yonge Street measured some 34 miles and 53 chains . For the rest of 1796 , Jones spent his time surveying Newark , Flamborough , Grimsby , Saltfleet , Beverley , York and Coot 's Paradise . 
