A stiff but shortish climb to the top but any pauses are worthwhile for the views to the south. The southern "entrance" is a bit of a puzzle. The notice board says that the main entrance is in the NE quadrant where the banks and ditches are much larger and deeper as the spur levels off here. At the southern "entrance" the banks and ditches peter out on either side which seems curious as, although the hillside is steep, it seems odd that this part is less defended.
The hill is capped with a layer of clay-with-flints and I just wonder if there has been a slippage down the hill, destroying the banks and ditches.
The tumulus and the pillow mounds are easily visible and the possible dew pond certainly had water in it when I visited.
A great place to visit (in good weather) with buzzards wheeling overhead, sheep peacefully grazing and stupendous 360 degree views.
You really have to want to see this hillfort, it's quite a climb, but utterly worth the effort. It's a large multivallate Durotrigian hillfort, which being built on the highest hill in Dorset is an obvious site for a defensive position. The 360 degree panorama affords views of nearby Lamberts castle, Coneys castle,Lewesdon Hill and the more distant Abbotsbury castle. Today I can see Portland which is about 35 miles away , the last time I was here visibility was about 35 feet.
Pillesdon Pen is a remarkably high hill, a mile north from the village. On its easter limit, near the turnpike road leading from Broad Windsor to Furzemoor Gate and Lambart's Castle, is a large and very strong Entrenchment, encompassed with a triple rampart and ditches, excepting on the eastern summit, where the natural ascent is so steep, as to have rendered the camp inaccessible. The form of this Camp is nearly oval, being adapted to the shape of the hill on which it stands.
Fuller, in his Worthies of England, mentions a proverbial saying current here; "as much a-kin
As Lew'son Hill to Pil'son Pen;"
which was spoken of such as have vicinity without acquaintance.
The two hills are within a mile of each other, and form eminent sea marks: the seamen denominate one the Cow, and the other the Calf, from their imagined resemblance to those animals when beheld from a distance.
From p525 in The Beauties of England and Wales, Or, Delineations, Topographical, Historical, and Descriptive of each County. Vol 4. John Britton and Edward Wedlake Brayley, 1803. Online at Google Books.
The National Trust booklet 'The Cerne Giant & Dorset Hill-Forts' (2000) which is definately available at the Kingston Lacy house and might be available at other Dorset properties, gives the following directions to the hill fort at Pilsdon Pen, "Take the B3164 west out of Broadwindsor. This winding road skirts the northern edge of the Marshwood Vale. After 4km you will see the ramparts and ditches of Pilsdon Pen hill-fort come into view at the southern end of a high flat topped ridge. Park in the lay-by just after the turning to the hamlets of Pilsdon and Bettiscombe. Cross the road and walk up the steep slope".
It adds that the name 'Pilsdon' is Old English for a hill with a peak. The earliest documented reference to the place name dates from the Domesday Book in 1086.
Pilsdon Pen (the name is a part Celtic name, pen being well known to all walkers in Wales as the local name there for a hill) is the highest hill of Dorset, standing 277m - that is 908 feet above the sea, 92 feet short of being a mountain!?