Barrydale has a rich history dating back to 1840, when John Barry (a member of the powerful Barry family and after whom the nearby town of Barrydale was named) opened up the small harbour of Port Beaufort at the mouth of the Breede River. In 1858 local farmers had petitioned government to build a road to the interior to help them get their goods to the port. By 1867 their efforts were rewarded when parliament approved funds of one thousand Pounds Sterling for the proposed road and the Divisional Council appointed 'wunderkind' Thomas Bain to do the job with the help of 300 convict labourers.