Wollaston was developed as a linear settlement starting at what is now Cobbs Lane moving past Bell End, Rotten Row, St Michaels' Lane and down towards Strixton.
Settlement and activity in the area are known to date from at least Roman times. Remains of a large (35 hectare) Romano British vineyard are known in Wollaston, and are some of the first such sites confirmed in the United Kingdom. A Roman road passes roughly east-west just south of the modern part of Wollaston; another Roman road passes north-south to the east.
There is strong evidence of Saxon settlement and activity, including the discovery of one of the finest Saxon-style iron helmets in a warrior's grave dating from around 700 AD. It is thought that the name Wollaston comes from Wulflaf’s Town, Wulflaf being an early Saxon.
The oldest visible part of Wollaston is known as Beacon Hill, an ancient castle earthwork or burial mound which once belonged to Bury Manor. The mound was once surrounded by a great ditch which dates back to the 12th century. A wall plaque records that this was the site of a Motte & Bailey Norman castle.
Margery de Wolaston - was elected in 1282 as the Abbess of Delapré Abbey in Northampton; she died circa 1296.
In 1788 Wollaston land was enclosed under an act of parliament, at the time David Hennell, a lace dealer from Wollaston wrote "I lament that this field is now agoing to be enclosed. Some that have large quantities of land are set upon it, and pay no regard to the many little ones that may be injured, and I fear many ruined." The enclosure reduced the number of landowners in the village from 108 to just 18.
Wollaston's first school opened in 1842 and was located in a building adjacent to the Indian restaurant (formerly The Cuckoo pub), opposite Bell End. The school was private and was run by a curate, the Reverend J.J. Scott, from his own funds. The school did not come under government control until 1873. The school has moved several times, finally being established on College Street in a building dating from May 1894.
During this period significant industry came to Wollaston in the form of shoe- making and farming. In 1885 one of the shoe factories was established as a workers' co-operative of local cobblers, which survived until the 21st century as Northamptonshire Productive Society and remains a shoe factory as NPS (Shoes) Ltd, making shoes under the George Cox, Tredair, Solovair and NPS brands among others. The Wollaston Vulcanising Co-Operative was another local business.
Shoe-making, and the mechanisation of this work, continued in the early 20th century with a number of nationally-known shoe-making companies establishing themselves in Wollaston and surrounding area.
In 1940 Scott Bader moved manufacturing Wollaston from London; the move became permanent and the company is now an integral part of the local community. The company founders, Ernest Bader and Dora Scott, established the Scott Bader Commonwealth in the 1950s, gifting the whole company to its employees for all time. The company now functions as a co-operative with profits divided between investment in the company, bonus for employees and charitable donations. In the early 70's to late 90's wollaston was also the home to LSM engernering which specilised in making working steam engines but to a much smaller scale.