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"The town is populous, tho' not large, the streets broad, but the buildings old, and low; however, there is good company and a good deal of it; and a man that coveted a retreat in this world might as agreeably spend his time, and as well in Dorchester, as in any town I know in England". -- Daniel Defoe, in Tour through the whole island of Great Britain (1724 - 1726).

In 1613 and 1725 great fires destroyed large parts of the town, but some of the mediaeval buildings, including Judge Jeffreys' lodgings, and the Tudor almshouse survive in the town centre, amongst the replacement Georgian buildings, many of which are built in Portland limestone.

In 1642, just prior to the English Civil War, Hugh Green, a Catholic chaplain was executed here. After his execution, Puritans then played football with his head.

In the 17th century the town was at the centre of the Puritan emigration to America, and the local Rector, John White, organised the settlement of Dorchester, Massachusetts.

The town was heavily defended against the Royalists in the English Civil War.

In 1685 the Duke of Monmouth failed in his invasion attempt, the Monmouth Rebellion, and almost 300 of his men were condemned to death or transportation in the "Bloody Assizes", held in the Oak Room of the Antelope Hotel, Dorchester and presided over by Judge Jeffreys.

In 1833, The Tolpuddle Martyrs formed the Friendly Society of Agricultural Labourers. However, despite trade unions now being legal and due to them actually swearing an oath of allegiance, they were arrested and tried in the Shire Hall in Dorchester. This building still remains and is preserved as it was at the time. Under the court are the cells in which prisoners were kept while waiting for their appearance in court.

Dorchester remained a compact town within the boundaries of the old town walls until the latter part of the 19th century, due to the ownership of all land immediately adjacent to the west, south and east by the Duchy of Cornwall. This land composed the Manor of Fordington, and a select few developments had encroached onto it:

The Marabout Barracks, to the north of Bridport Road, in 1794
The Dorchester Union Workhouse, to the north of Damer's Road, in 1835
The Southampton & Dorchester Railway and its station east of Weymouth Avenue, in 1847
The Great Western Railway and its station to the south of Damer's Road, in 1857
The Water Works, to the north of Bridport Road, in 1854
A new cemetery, to the west of the new railway and east of Weymouth Avenue, in 1856

This remaining Duchy land was farmed under the open field system until, in 1874, after repeated attempts by both landowner and some residents, the land was enclosed - or consolidated - into three large farms.[9] Soon afterwards followed a series of key developments for the town: the enclosing of Poundbury hillfort for public enjoyment in 1876, the 'Fair Field' (new site for the market, off Weymouth Avenue) in 1877, The Recreation Ground (also off Weymouth Avenue) opening in 1880, and the imposing Eldridge Pope brewery of 1881, adjacent to the railway line to Southampton. Salisbury Field was retained for public use in 1892, with land being purchased in 1895 for the formal Borough Gardens, between West Walks and Cornwall Road.[9] The clock and bandstand were added in 1898.[10]