So far, so good

I've been to the gym a couple of times this week, and I'll be going again tomorrow morning. I ran on the treadmill today, and earlier this week I put in a session on the elliptical. I do have a question, though. At what settings should I be using these machines to achieve exertion similar to jogging down the street? I get so proud of myself because I run for 2 or 3 miles on the treadmill at a pretty good clip, but I can't achieve similar results when I do my real-world running. Advice? I'd like to run more outside, but during the times that work for me to exercise (early mornings), it's pitch black out there, with little lighting on the street. (Plus, it's COLD!!) :-)