The following information is from Williams (2003). The English undertook the first permanent European settlement on the island in 1650. The sugar industry on Anguilla suffered throughout the 17^th and 18^th centuries due to drought and a lack of investment capital by local planters. Anguillian settlers owned small plots of land, and typically only a few slaves worked with them and their family members in the fields. Slavery did not become fully established on Anguilla until late in the 18^th century, and even then, the ratio of slaves to whites and free coloreds never matched the proportions found in other Caribbean plantation economies. The 1750 population information for Anguilla shows 350 whites, 38 free coloreds, and 1,962 blacks. The census of 1830 reveals the following demographics: 200 whites, 399 free coloreds, and 2,600 blacks. The 1830s on Anguilla saw a period of prolonged droughts that destroyed food crops, animals, and caused human famine.

After emancipation in 1838, a number of white colonists left the island to settle in North America and other parts of the Caribbean. The general distressed conditions of Anguillian life prompted some Anguillians to work as indentured laborers on the sugar plantations in St. Croix during the 1870s. The 1880 census of the island shows 202 whites and 3,017 free coloreds and blacks. The end of the 19^th century brought Anguilla a devastating drought and corresponding famine.

Until recently Anguilla was relatively isolated from other islands of the area. Phone service was not available on the island until the 1960s. Electricity was not brought to the far eastern end of the island, to the villages of Island Harbour, East End, and Mount Fortune until the 1980s. The most recent census of May 2001 reveals a population of 11,300 for Anguilla.

Williams (2003) is the only source for linguistic features in Anguilla. His research focuses on the Webster dialect of Island Harbour, a white enclave dialect of English in the Eastern Caribbean. Non-Afro-American Anglo-Caribbean varieties, i.e. those English varieties spoken among the descendants of Irish, Scots, and English settlers, have largely been ignored within research paradigms except for the work of Williams (1985, 1987). These English-derived language varieties spoken largely by Euro-Caribbeans on the Bahamas, Saba, St. Barts, Bequia, the Cayman Islands, Barbados, and Anguilla may shed light on the Anglophone component heard by Africans and Afro-Caribbeans working alongside many of these European immigrants. Historically, these white indentured servants were often treated socially no differently than African slaves; some of them even joined African-derived Maroon communities. Williams (1987, 1988) uses the term Anglo-Caribbean English to designate the variety spoken by these speech communities.

Williams’ research reveals some phonological features that are clearly derived from Scots or Scottish English sources. Unlike other dialects of English spoken in West Indian white enclave communities such as Cherokee Sound in the Bahamas, the Webster variety does not exhibit a significant degree of h- dropping. Williams correlates this pattern with the fact that there is no h-dropping in Scotland (Volume 1 of Wells 1982: 412). (However, the absence of h-dropping is a regional feature of the Eastern Caribbean in general.) Another feature associated with the Scottish component of this variety is that lexical items with vowels similar to mouth in metropolitan varieties are typically realized with the Scots pronunciation /u/.

The Webster dialect is primarily non-rhotic, although [r] is variably pronounced in some contexts by some speakers, e.g. [g^yanʔfaðər] grandfather, [wamz] worms. The Webster dialect exhibits the /w/ and /v/ alternation (typically with the intermediate value of [ß] ) that is found in many of the English-derived languages of the Eastern Caribbean and beyond. The Webster dialect differs in this regard from the Bahamian white dialect of Cherokee Sound where only the use of v in place of w was recorded by Childs, Reaser, and Wolfram (2003).

Th-stopping is a feature of the Webster dialect and other dialects of Anguilla, e.g. [diz] these, [doz] those, yet there are instances of interdental fricatives, e.g. [g^yanʔfaðər] grandfather. There is a degree of variation in the replacement of the fricatives with the corresponding stops, especially in careful speech. Williams (2003) states, “[c]ontext and the effect of vernacular language loyalty are the factors that affect whether pronunciation /θ/ and /ð/ will occur”. Similar factors are discussed in Aceto (fc.) for the St. Eustatius speech community and in Cutler (2003) for Turks Island English.

The Webster dialect also exhibits a slight degree of palatalization of velar stops before non-back vowels, e.g. [g^yɪlz] girls, [kyarɪʤ] carriage but [golʔ] gold, [kolor] color. Other features include the intervocalic voicing of /f/, e.g. [nevuz] nephews, and the lenition of word-final /t/ and /d/ when preceded by another consonant, e.g. [golʔ] gold, [ainʔ]  ain’t.