Mt Crawford sits above Point Hallswell at the northern tip of the Te Motu Kairangi / Miramar Peninsula, Wellington. You can drive to the top from Miramar Drive onto Maupuia Road, then Akaroa Drive. At the top is the derelict Mt Crawford Prison, dating back to the 1920s and closed around 2012. The land was to be used for housing, but the project has been affected by Māori land disputes. But the delay does make a visit to Mt Crawford a bit more interesting.
When you park, you will see a closed road between the pine trees above the Miramar community gardens. Go through the gate (ignore the sign); it is an easy walk along the road until you see the WWII concrete gun emplacements above the point. The graffiti artists have been busy, and some is quite colourful. The best views of the harbour and back to Wellington are from the emplacements.
If you follow the road a bit further, or just walk northeast below the emplacements you will find access to the (by NZ standards quite spectacular) Memorial to William Massey, a long-serving NZ prime minister who led during WWI.
Keep following the road and you will end up in Shelly Bay.