I run all over the place and have never felt unsafe! Harbor Point is a great area for running, but I do most of my long runs around Darien and Rowayton. You can park for free in Darien and run along all the wide roads through Rowayton all the way to South Norwalk. Scalzi park is well-lit after dark. There’s also a great loop at Waveny park in New Canaan that backs up to the New Canaan high school track. The tracks at Darien high school and Wilton high school are also public and they’re great. I recommend Mianus River Park for trail running, too.

Basically if you’re willing to drive a bit, there are loads of great options! Message me if you want a running buddy 👍🏼