People have been living on the land in Stratton for over 5,000 years. The earliest record of Stratton (meaning 'the farm on the road') was the Saxon village but this can only be proved by a few pottery sherds and land boundaries which have survived. After the Norman Conquest Stratton was owned by Salisbury Cathedral and the land leased to a succession of tenants. Some of the open fields survived until 1895 when the last of the land was enclosed and sold freehold becoming the Wrackleford Estate.

On Grimstone Down an earlier settlement was occupied during the Iron Age and Roman periods. The name Grimstone was spelled 'Grimston' in medieval times and means 'the farm belonging to a man named Grim'.

Other ancient features in the Parish include Bronze Age burial mounds and the Roman road from Dorchester to Ilchester which passed across the valley. One notable tenant farmer, Angel Smith who lived in Stratton Manor House and died in 1626, was described as 'Lord of Stratton, 58 years'. One of his daughters married into the Grey family of Kingston Maurward.

The base of Jackmans Cross is near the crossing of bridleways on Grimstone Down. A bench and new stone Cross mark the Millennium. The story goes that Jackman was gibbeted near here for sheep stealing in medieval times. The landscape reflects sheep farming around here in the recent past. The Barns are mostly remembered in name only but 'Meaders' in Grimstone still survives. Dairying is now the major livestock activity, with cereal production in the large modern arable fields. Stratton and Grimstone Mills still have their wheels; Grimstone Mill being on a site which dates back to the 14th Century.

St Mary's Church; of Norman origin on a Saxon site was largely rebuilt in 1890/1. Thomas Hardy, then an architect, helped to preserve the 15th Century tower with its unique wooden staircase and the remains of a Preaching Cross in
the Churchyard. The chancel was rebuilt by Alfred Pope in memory of his first wife at the same time.

The Saxonfield housing development of 1999 is on the site
of West Hall, the old Manor of Grimstone now demolished.

Three cottages made up the house known as 'Cowleaze'. Their land was enclosed in 1670. Church Farm was built in the 17th Century with later additions. The little cottage which has only in recent times been known as 'Plague Cottage' is similar in age. Others, notably 'John Lock's', 'May's', 'Chapel' and 'Rose and Ivy' cottages are typical flint and brick buildings
of the early 19th Century.

Wrackleford House featured in 1669 as 'Ye farme of Wrackleford, belonging to the Pitt family. Subsequently Robert Pattison and one of his daughters, the Hon. Mrs. Jane Ashley-Cooper lived there. The Almshouses and the Church Institute (now the Old Village Hall) were built in her memory. Alfred Pope and succeeding generations of his family have made Wrackleford House their home since 1888.

The Toll Cottage, built 1798 stands where the main Turnpike Road from Maiden Newton to Dorchester branched to Winterborne Abbas at Brewers Ash. The Wiltshire, Somerset and Weymouth Railway came through the Parish in1856.
Note the viaduct at Grimstone, designed and built by Isambard Kingdom Brunel, and the remains of two stations
at Grimstone and Ash Hill.

The houses at Ash Hill were built in 1950.