Pilgrims' Cross Primary School is situated on Picket Twenty, a village which was once a hamlet and is now effectively a suburb of Andover. Pilgrims' Cross gets its name from being the crossroads of two popular pilgrims' routes: the Old Harrow Way that ran from Seaton in Devon to Canterbury and the pilgrim route that ran from London to Bristol. Picket Twenty was a busy crossroads where these two routes crossed.

The eastern part of the Harrow Way or Old Way from Farnham, Surrey, is a popular footpath, romantically dubbed the Pilgrims' Way in the 19th century. Farnham was an aggregation point for travellers joining from the south coast.^[6] Gibson reports the section going eastward just north of Farnham ran through the area now Farnham Park and continued its course along the chalk outcrop. The Harrow Way then continues to the crest of the Hog's Back, where the ancient trackway is known to have run. 

The western part of the Old Way, the Harrow Way, can be traced from through Basingstoke and Andover to Salisbury Plain and Stonehenge, Wiltshire through Dorset and on to Seaton on the Devon coast. 

In the Picket Twenty development, the street names identify themes which have some reference to the site, its characteristics and history. Following research and having regard to the existing street names in Andover, the following themes were considered for Picket Twenty - coaching / transport, horse racing, Harewood Forest and farming.

Boulter Road and Boulter Crescent were named after a local highwayman called Thomas Boulter. He was renowned for holding up the coaches between Southampton and Salisbury and from London to Salisbury, particularly when they travelled over Salisbury Plain.

Blinker Way is named after the blinkers used on horses' heads in races.

Quicksilver Way refers to the name of a coach from Exeter to London which was deemed to be the fastest coach in England in 1844. It took 17 hours to travel between London and Exeter.