In reply to jamesc88:
You can bypass the standard boggy bit at the bottom of the field by walking through the village to join the track where it meets the road. It's not much further and is generally much more pleasant if it's muddy underfoot.
In reply to Kevster:
From the Square and Compass, follow the road to the right of the pond and past the church. As you leave the village, there's a big track on the left with a fingerpost signed Winspit. http://goo.gl/maps/nyyOf
Swanage was in great nic today. Top outs solid too. We were the only team at Boulder Ruckle for the first half of the day. T shirts as it was hot. Very little damp on routes. Have fun those who go tomorrow.