How long will the journey take? Welcome Back Services - 1st-14th August The total journey time will be approx. 1 hour. Departure times from Pickering and Grosmont – 09:30 / 11:30 / 13:30 / 15:30 The last train arrives back into Pickering or Grosmont at approx. 16:30 'The Optimist' - 17th - 30th August Service 1: The Pickering departure at 09:20 will depart Whitby 14:00, allowing approx 3 hours in Whitby. Service 2: The Pickering departure at 12:00 will depart Whitby at 16:30, allow approx 2 hours 45 mins in Whitby.