I have been trail running in the evenings lately. It's a common problem isn't it. Busy days and full schedules sometimes leave little time for R & R. ( my wife would say, "get up earlier!). Anyway, I am very fortunate that I can run on a full stomach fairly soon after dinner and have been doing some gorgeous sunset into darkness runs around where I live. The route doesn't really matter at the moment, I am really enjoying the still evening air, people are still out and about riding or walking their dogs in the parks. The light seems to cling to the hills well past sunset and the temperature is still hovering around 20C (68F) after dark.
You can trail run in New Zealand all year, with some restrictions in Mountain passes during the winter. Though in my opinion the ultimate time to travel to New Zealand is at the end of summer during late February, March and April and even into May. We have daylight savings in NZ and the sunset is extended 1 hour each night until early April giving plenty of daylight hours and most importantly, the weather is also generally settled.
Okay, I am living in the moment a little bit, there were plenty of clear crisp clear days in winter last year when I wondered if the snow would ever arrive and I was bounding around in shorts and t-shirt. The weather in New Zealand is fairly benign or temperate really, and usually the weather bombs are very well forecasted by www.metservice.co.nz and the conditions improve again shortly afterward.