My wife and I left home after dark, and we did 1.9 miles in our neighborhood. She stopped to talk with a friend but soon caught up with me. Before I started running on canal maintenance roads and the Jordan River Parkway, I did all my running on neighborhood streets. I found that by running all streets and cul-de-sacs, I could get about 5 miles. When my distance got bigger than 5 miles, I started running on canal maintenance roads and later on the Parkway. The sidewalks around here are bumpy due to frost heaves and ground settling, but the streets are pretty smooth. My goal is to add 5-10% each week to extend my distance. As my distance gets longer, the amount I add each week gets longer too. Even though daytime temperatures are in the 90s (F), the early morning and evening temperatures are in the 70s, and that helps.
The following picture was taken from the web.