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 towards the end of September).
That is normally when hurricane warnings really loom.
My family had the pleasure of experiencing Hurricane Omar in October 2008...

Barnes Bay, October
(I don't think Dad and I would take those waves on, hehe! ;-)
I wasn't there to share the pain of the hurricane with my family. Hurricane Omar didn't sound particularly dangerous, but very uncomfortable. Living in tropical weather without electricity and running water did not sound like fun.
If you're traveling to Anguilla in September and October take note of the hurricane warnings
Unlike September though, there is far less heat and humidity, but there are buckets of rain...
Average High in October: 87°F
Average Low in October: 77°F
Average Temp. in October: 82°F
Average Rain in October: 6"
October seems to be one of the less exciting months in Anguilla, with most bars and restaurants still boarded up, hurricanes still have a chance of swooping in, and there is an endless amount of rain.
Typically, not many people travel to Anguilla in October.
Anguilla travel tip: October is still a hot and sticky month. Leave any heavy clothing behind.
Update: Click here to read about my family's extreme Anguilla weather experience with Hurricane Omar in 2008.

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