Sep/Oct is to late to be hiking in the highlands in my opinion. The weather is very unpredictable and winter storms are common.
If you hike along the ring road and stay close to populated areas you can be relatively safe but expect lots of rain and high winds. A few calm day´s maybe if you are lucky.
As far as hiking in the south or north depends more on weather forecast. It´s really impossible to predict where the weather could be better. It all depends on where the low pressure areas hit the island at a given time.
I am a rescue pilot and we have to go search for missing people often. Locals usually will not hike the highlands in october and if they do it´s with a group and good planning.
If you wander of the beaten path please download the 112 app 112 Iceland App - safetravel.is and rent a personal locator beacon or buy a Spot locator. Also make sure you have plenty of battery for your phone. We can find you even if you are outside cell coverage area.
Don´t go Bear Grylls Man vs wild on us That´s all fake.
Fun show as entertainment though: Man vs. Wild_“Iceland Fire and Ice" s07-e03 - Video Dailymotion
Check out this link for hiking trails: HIKING ROUTES TRAILS IN ICELAND
Have a nice visit.
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