Map yourself a route down Shippan! That’s where I used to run when I lived in Stamford.

Warning: I’m about to gush about my favorite running place in the whole world, so this is gonna be a long post :)

It’s an incredibly safe area, and with all of its roads you could loop yourself in and out of tons of scenic routes. Shippan has some beautiful homes and even more beautiful landscaping. Also some slightly challenging roads in terms of incline - Shippan Ave itself is mostly flat with a slight decline towards the end, but a lot of its intersecting roads have steep hills and are just great for short bursts.

IMO much better than running in the woods (due to safety). Just be wary that some cell users have patchy service towards the peninsula - but it doesn’t mean you won’t be able to call 911, obviously. I’m also 95% sure you’d be able to find a group of runners who live in or frequent Shippan, if you’re into a group workout.

My route started by the West Beach entrance. I’d run down towards the beach, past both soccer fields on left and baseball on right, following the path behind the pumping station brick building, leading towards Rippowam. I’d either head up Iroquois or follow along the path by the wave breaker towards Lanell. I’d run down Shippan Ave and would just go wherever my heart desired.

-Ralsey and Sagamore are both steep hills, so I liked to do those on my way back out.

-Ocean Drive West is beautiful to run southwest along on during sunset. Views across the water through backyards all the way down, with an AMAZING sunset spot at the end of Fairview Drive at the beach. You can also view the ‘castle’ of Shippan along this route.

-If you’re doing a sunrise run, stick to the eastern side. At the end of Hobson there is a small area adjacent to the rocks of the beach club where you can walk out towards the water. It’s directly to the right of the house at the end of the road; 10/10 spot. Also an incredibly beautiful view from the very top of Ocean View Drive, just around the corner, but this one gets a 9/10 only because there isn’t a spot to sit down.