Although hurricane season begins June 1st, the "riskiest" time to be in Anguilla is during August, September and October (with the "peak of peaks" being the last weeks of August and stretching to the end of September).
That is normally when hurricane warnings really loom. If you're traveling to Anguilla in September and October take note of the hurricane warnings.
Storms aside, October is the rainiest month of the year...
Average High in October: 87°F
Average Low in October: 77°F
Average Temp. in October: 82°F
Average Rain in October: 6"
That is, of course, a relative term. Anguilla is one of the sunniest islands in the Caribbean.
It does not rain every day and the weather is usually clear and warm - unless a storm passes through.
Weather aside, October is one of the quieter months in Anguilla. Things get exciting towards the end of the month when certain bars and restaurants will start re-opening.
Not many people travel to Anguilla in October. But, those who do are able to enjoy beaches all to themselves!
Anguilla travel tip: October is a hotter month. Leave any heavy clothing behind.