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Mainly letters written and received between 1770 and 1835 by Simon Taylor, his family and heirs, and his friends, agents and business partners, relating to their Jamaican estates and business interests. Over a quarter are contained in Simon Taylor's letterbooks. Though the majority of the correspondence consists of letters either to or from Simon Taylor up to his death in 1813, there is also correspondence of other family members, like his brother Sir John Taylor (1741-1786) and his widow Lady Elizabeth Haughton Taylor (1758-182[?2]), their son and his heir Sir Simon Richard Brissett Taylor, and his cousin and business partner Robert Taylor. Subject matter ranges from the domestic (illness, family quarrels, disinheritance, bigamy) to business (slaves, sugar, trade and shipping, the effects of hurricanes, the introduction of a steam engine on an estate), to the Maroon and French wars and the politics of Abolition. The collection also includes correspondence of George Watson Taylor, 1815-1819, and detailed reports on the estates made for Anna Susannah Watson Taylor in 1835. Genealogical tables for the Taylor, Haughton, Brissett and Hibbert families have been added to the collection at a later date.

The records comprise deeds and legal, administrative and financial papers relating to the Castle Wemyss Estate, Jamaica, 1802-1845, belonging (during the period covered by the papers) successively to Gilbert Mathison, Simon Halliday and Rev Walter Stevenson Halliday. The deeds and legal papers record the ownership of the estate and financial claims upon it by other parties, as well as compensation claims under the Abolition Act. They include the title deeds to the estate 1802-1845; together with correspondence and other papers concerning financial claims upon it (particularly an annuity payable to Catherine Mathison, widow of Gilbert) 1830-1845, compensation payable under the Abolition Act 1834-1835, and the fate of the estate in 1843-1845 when it was no longer viable financially.
The administrative and financial papers illustrate the management of a West Indian sugar estate by attorneys on behalf of absentee landlords, and the process of shipping the sugar and rum produced back to London for sale by a firm of merchants. A fairly complete series of correspondence between Simon Halliday and his attorneys and merchants survives for the period 1823-1828, giving many details of the practical problems of managing a sugar estate and of ensuring an adequate performance by the attorneys. There are many reports on the progress of crops, as well as references to maintenance work required, the need for new cattle (a continuing problem on the Castle Wemyss estate) and the work and health of the slaves. There is further detailed information on the slaves in a series of returns; in addition there are lists of them in the title deeds to the estate after 1807 (following the abolition of the slave trade). There are references to specific events involving the slaves in the correspondence and/or the returns: for example, the case of Catalina alias Susannah Mathison who induced an abortion by taking Vervain and Contrayerva in 1824; and allegations of mistreatment of the slaves by one of the overseers, in 1827.
The correspondence of 1823-1828 also includes letters between Halliday and the firms of merchants he used in London to sell his produce. The state of the sugar and rum markets are regularly discussed, and both attorneys and merchants report on the despatch and receipt of shipments of sugar and rum, on which the successful running of the estate depended. There is one instance of a ship being wrecked and part of the cargo lost.There are also financial accounts, both of the attorneys and of the merchants, which illustrate the returns and financial problems of the estate.