Ravenscar to Robin Hood’s Bay and back.

You have various options here:
1. Park up at Ravenscar and walk (3.5 miles) the Coastal Path in one direction, stop for lunch in Robin Hood’s Bay and return the same way.  This starts you off with a steepish descent and therefore a steepish climb to finish.

2. As above, but return on the Cinder Track (5 miles), which is a far gentler, gradual climb and kinder on the knees. The Cinder Track is the bed of the former railway.

Parking is free in Ravenscar. You can park on the edge of the village as you drive in, where there are handy loos; if it’s busy, follow the road round the corner, head for the Tearooms and there’s a free parking area opposite the old station.

3. Leave a bike/bikes at Ravenscar - there is a bike park outside the National Trust building - then drive up to RH Bay, park in one of the 2 car parks at the top of the village, walk back the Coastal Path route, retrieve the bike(s), ride the Cinder Track back to the car.

4. As above, in reverse. You could leave the bikes at   in RH Bay and park in Ravenscar.

The main problem is that the walk and bus option is not really viable as Ravenscar is 3 miles from the A171, so ingenuity or a long circular walk is required.

So, from Ravenscar:
Start from the National Trust building which is near the Raven Hall Hotel.  You can’t miss it! Call in the NT visitors’ centre as there’s a good little exhibition about the folly that was Ravenscar Resort. You can see RH Bay clearly in the distance
Walk down the path and make sure you take the Cleveland Way signed route. This is where the Cinder Track will bring you out at the end.  The path drops fairly steeply at first - not uncomfortably so - and then soon levels out. Pass through an area of woodland. You will come to the derelict Alum works and again it’s worth reading the information boards.
Follow the path past meadows, sheep pasture and arable crops. It’s pretty level most of the time and easy walking. The path will drop down a short series of steps and back up again, then further on a longer set of steps will take you to beach level and back up.
The third set of steps is Boggle Hole. Here, you’ll find a beach and a Youth Hostel (cafe and loos).
The path winds on along the cliff top - just follow the signs.
Eventually, as you’re nearly in RH Bay, the path meets a T-junction. Turn left and you’ll drop down steps into the village, coming out near the jetty. Turn right and you’ll come out on the beach which is fine if the tide is out. If unsure, turn left!
If you don’t know RH Bay, it’s basically 2 streets with the sea at the bottom, car parks at the top and a variety of eateries, pubs, ice cream shops, gift shops etc. in between.  There’s a fish n chip shop at the bottom and another at the top of the village.
When you’re ready to move on, walk up the main street, across the little roundabout (car park on left) and walk a little further on, past the Post Office towards the next car park, where there are loos.
Turn left in front of the car park, signed Cinder Track.  This will take you along a short tarmac road and bring you out on a busier road. Cross the road, bearing right and you’ll see the Cinder Track. You now have a steady 5 mile walk along a wide path, rising very gently back towards Ravenscar. It dog-legs across a little road at one point. There’s plenty of shade but not many ‘big views’. The Cinder Track comes out just below the National Trust building.
To give an idea of time, we set out on the Coastal Path at 11:20, stopped for a wander and lunch at RH Bay and returned along the Cinder Track at a steady speed, reaching the car at 16:00.
There is not much to Ravenscar apart from the Hotel and Golf Course (not investigated) and the seasonal and friendly Tea Rooms by the old station. They’re open daily in season, selling drinks, light meals, cakes etc.  Recommended by us.
You can get drinks from a machine in the NT centre.

From Robin Hood’s Bay:
See above for access to the Cinder Track if you’re choosing that option.
For the Coastal Path, walk down the street to the jetty. Just before you reach the bottom, look for a narrow road (Albion Road) on your right which has a tiny fish n chip shop on it. Walk about 75 yards and turn left up the Flagstaff Steps which are the start of this section of the Cleveland Way. Follow the signs for 3.5 miles and the path will bring you out by Ravenscar NT centre.

The Cleveland Way

There are numerous websites available which give information about the Cleveland Way, books too, but it’s never quite the same when you tackle somewhere new yourself. They are often written by folk who know an area intimately and who therefore assume you know where you’re going at every turn. But in most cases, you want a one-off walk and need to get it right first time.

You can, if you want, tackle the Cleveland Way in one fell swoop, starting in Helmsley and finishing in Filey, or vice versa. It is possible. There are companies that will sort out accommodation and/or transfer your luggage. Otherwise, you may decide to do it as we have, in sections. Some sections are obvious and relatively easy to organise - Whitby to Robin Hood’s Bay, for example - while others need more planning and possibly 2 cars.